Aniline → [5-Fluoro-2-methyl-3-(2-phenylsulfamoylbenzyl)indol-1-yl]acetic acid methyl ester

HRID 1944427Notes

Reaction equation

HRID 1944427 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:15][O:16][C:17](=[O:41])[CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[C:21]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[S:36](Cl)(=[O:38])=[O:37])=[C:20]1[CH3:40]>ClCCl>[CH3:15][O:16][C:17](=[O:41])[CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([F:28])=[CH:25][CH:26]=2)[C:21]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[S:36](=[O:38])(=[O:37])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:20]1[CH3:40]

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 86652191[3-(2-Chlorosulfonylbenzyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester

Product 1

HCID 67045012[5-Fluoro-2-methyl-3-(2-phenylsulfamoylbenzyl)indol-1-yl]acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of aniline (0.022 mL), triethylamine (0.051 mL) and dichloromethane (0.5 mL) was treated with [3-(2-chlorosulfonylbenzyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester (0.10 g), and resulting mixture was stirred at room temperature for 4 days. The mixture was diluted with dichloromethane, washed with water and concentrated under reduced pressure to afford the title compound as a colourless gum (0.078 g).

Workup

  1. customresulting mixture
  2. washwashed with water
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8dc7d95e33364601a613861b52f5e7a1
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

Loading…