Process for making organic compounds and the organic compounds made therefrom
View Patent ↗An organic compound of formula E is made from a process comprising: reacting a compound of formula A and a compound of formula B to form a compound of formula C; and reacting one of the compound of formula C and the compound of formula D with a first boron esterification reagent to generate a boronic acid or a boronic ester to react with another of the compound of formula C and the compound of formula D to form a compound of formula E; wherein R 1 , R 2 , and R 3 are, independently at each occurrence, a C 1 -C 20 aliphatic radical, a C 3 -C 20 aromatic radical, or a C 3 -C 20 cycloaliphatic radical.
1. A process comprising:
reacting a compound of formula A and a compound of formula B to form a compound of formula C; and
reacting one of the compound of formula C and the compound of formula D with a first boron esterification reagent to generate a boronic acid or a boronic ester to react with another of the compound of formula C and the compound of formula D to form a compound of formula E;
wherein R 1 , R 2 , and R 3 are, independently at each occurrence, a C 1 -C 20 aliphatic radical, a C 3 -C 20 aromatic radical, or a C 3 -C 20 cycloaliphatic radical;
X1 is chloro, bromo, trifluoromethanesulfonate, or hydroxy;
X2 is chloro, bromo, iodo; and when X1 is chloro, X2 is bromo or iodo, when X1 is bromo, X2 is iodo, when X1 is hydroxy, X2 is chloro, bromo or iodo, when X1 is trifluoromethanesulfonate, X2 is bromo or iodo;
X3 is boronic acid or boronic ester;
X is CH or N and when X is CH, at least one of R 2 is pyridyl;
X4 is chloro, bromo, trifluoromethanesulfonate, or hydroxy;
X5 is chloro, bromo, iodo; and when X4 is chloro, X5 is bromo or iodo, when X4 is bromo, X5 is iodo, when X4 is hydroxy, X5 is chloro, bromo or iodo, when X4 is trifluoromethanesulfonate, X5 is bromo or iodo;
a, and c are, independently at each occurrence, an integer ranging from 0-4; and
b is an integer ranging from 0-3.
2. The process of claim 1 , further comprising converting the compound of formula E into a compound of formula:
wherein Ar is heteroaryl, aryl, alkyl or cycloalkyl, n is an integer ranging from 2-4.
3. The process of claim 1 , further comprising converting the compound of formula E into a compound of formula:
wherein Ar is heteroaryl, aryl, alkyl or cycloalkyl, n is an integer ranging from 2-4.
4. The process of claim 1 , further comprising converting the compound of formula E into a compound of formula:
wherein Ar is heteroaryl, aryl, alkyl or cycloalkyl, n is an integer ranging from 2-4.
5. The process of claim 1 , further comprising reacting the compound of formula E with a second borane esterification reagent to form a boronic acid or a boronic ester to react with a pyridyl dihalide to form a compound of formula I
wherein
R 1 , R 2 , R 3 , and R 4 are, independently at each occurrence, a C 1 -C 20 aliphatic radical, a C 3 -C 20 aromatic radical, or a C 3 -C 20 cycloaliphatic radical;
X is CH or N and when X is CH, at least one of R 2 is pyridyl;
a, c, and d are, independently at each occurrence, an integer ranging from 0-4; and
b is an integer ranging from 0-3.
6. The process of claim 5 , wherein the first and the second borane esterification reagents are pinacol diborane and the pyridyl dihalide is
7. The process of claim 6 , wherein the compound of formula D is of formula
8. The process of claim 7 wherein the compound of formula A is 1-chloro-3,5-dibromobenzene and the compound of B is of formula
9. The process of claim 8 , wherein the compound of formula C is of formula
10. The process of claim 9 , wherein the compound of formula C reacts with pinacol diborane to generate a compound of formula H to react with the compound of formula D.
11. The process of claim 10 , further comprising reacting 3-(3-bromophenyl)pyridine with pinacol diborane to form the compound of formula F.
12. The process of claim 11 , wherein the compound of formula E is of formula
13. The process of claim 12 , further comprising converting the compound of formula J into a compound of formula K
14. The process of claim 13 , wherein the compound of formula I is of formula II
15. The process of claim 7 , wherein the compound of formula C is of formula
16. The process of claim 15 , wherein the compound of formula A is 1-chloro-3,5-dibromobenzene and the compound of formula B is 3-pyridine boronic acid.
17. The process of claim 16 , wherein the compound of formula C reacts with pinacol diborane to generate a compound of formula M to react with the compound of formula D.
18. The process of claim 17 , wherein the compound of formula E is of formula
19. The process of claim 18 , wherein the compound of formula I is of formula III
20. The process of claim 1 , wherein the compound of formula A is selected from