Sodium Hydroxide → 3-(2-Fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1[S:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][C:17]=1[F:24])=[O:5])C.[OH-].[Na+]>>[F:24][C:17]1[CH:18]=[C:19]([S:22][CH3:23])[CH:20]=[CH:21][C:16]=1[NH:15][C:7]1[C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[S:14][C:6]=1[C:4]([OH:5])=[O:3]Participants
3
Conditions
- Temperature
- 60 °C
Procedure
A suspension of 3-(2-fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester (0.19 g, 0.52 mmol) in IMS (10 ml) was treated with sodium hydroxide (1M aqueous solution, 0.63 ml) and the reaction mixture heated at 60° C. for 3 hours. The resultant mixture was allowed to cool then concentrated in vacuo. The crude residue was treated with water and the mixture adjusted to pH 5 with acetic acid. The resultant suspension was filtered, the residue collected and dried in vacuo to give the title compound as a green solid (0.107 g, 56%) which was used without purification in the subsequent step.