Triethylamine → 1-Acetyl-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonic acid methylamide

HRID 1475324Notes

Reaction equation

HRID 1475324 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH3:19])([CH3:18])[CH2:11][N:12]2[C:15](=[O:17])[CH3:16])=[CH:8][C:7]=1Br)(=[O:5])=[O:4].C(N(CC)CC)C>CO.[Pd]>[CH3:1][NH:2][S:3]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH3:19])([CH3:18])[CH2:11][N:12]2[C:15](=[O:17])[CH3:16])=[CH:8][CH:7]=1)(=[O:5])=[O:4]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 709804931-Acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonic acid methylamide

Product 1

HCID 673767091-Acetyl-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonic acid methylamideYield 75.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonic acid methylamide (270 mg, 0.75 mmol), Pd/C (10%, 79 mg) and triethylamine (209 μL, 1.5 mmol) were suspended in MeOH (10 mL). The reaction was stirred under a hydrogen atmosphere for 1 h, then the mixture was filtered through Celite and filtrate was evaporated in vacuo to give the title compound (160 mg) as a white solid. 1H NMR (CDCl3): 8.65 (1H, s), 7.62 (1H, d), 7.26 (1H, d), 4.52 (1H, s), 3.88 (2H, s), 2.70 (3H, d), 2.26 (3H, s), 1.40 (6H, s). MS: [M+H]+=283.

Workup

  1. filtrationthe mixture was filtered through Celite and filtrate
  2. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-5af7d7e87eb44cf8b43e31006ea8ff7b
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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