Process for the synthesis of C-2, C-3 substituted N-alkylated indoles useful as cPLA
View Patent ↗The present invention provides method for making a compound of formula 1: comprising the steps of reacting compounds of formulas 2 and 3: to produce a compound of formula 4: wherein R 1 , R 2 , R 3 , R 4 and R 5 are defined as described herein. The compound of formula 4 is then converted to the compound of formula 1. The invention further comprises compounds of formulas 3 and 4 and methods for making compounds of formulas 3 and 4.
1. A compound of formula 3:
wherein:
R 1 , R 2 , R 3 , and R 4 each is independently selected from the group consisting of H, —CN, —CHO, —CF 3 , —OCF 3 , —OH, —NO 2 , —C 1-6 alkyl, —C 1-6 alkoxy, —NH 2 , —NH(C 1-6 alkyl), —N(C 1-6 alkyl) 2 , and —NHC(O)—C 1-6 alkyl; and
R 5 is selected from the group consisting of H and —C(O)O—C 1-6 alkyl.
2. The compound of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 each is independently selected from the group consisting of H, —CF 3 , and —C 1-6 alkyl.
3. The compound of claim 2 , wherein R 1 is —CF 3 , R 2 is H, R 3 is H, and R 4 is H.
4. The compound of claim 1 , selected from the group consisting of:
N-but-3-ynyl-C-(2,6-dimethylphenyl)methanesulfonamide, and
N-but-3-ynyl-C-(2-[trifluoromethyl]phenyl)methanesulfonamide.