Ammonia → 1-Acetyl-5-bromoindoline-6-sulfonamide

HRID 528827Notes

Reaction equation

HRID 528827 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:17])=[C:10]([S:13](Cl)(=[O:15])=[O:14])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[NH3:18]>>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:17])=[C:10]([S:13]([NH2:18])(=[O:15])=[O:14])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 140245841-acetyl-5-bromo-2,3-dihydro-1H-indole-6-sulfonyl chloride

Product 1

HCID 551511491-Acetyl-5-bromoindoline-6-sulfonamideYield 65%

Procedure

A solution of 1-acetyl-5-bromoindoline-6-sulfonyl chloride (2.30 g, 6.79 mmol) in NH3 (54.3 mL, 27.2 mmol, 0.5M solution in dioxane) was stirred at room temperature overnight. The reaction mixture was then concentrated in vacuo, and the residue was triturated with CH2Cl2 to give the title compound (1.40 g, 65%) as a brown solid. 1H NMR (DMSO-d6) δ 8.73 (s, 1H), 7.63 (s, 1H), 7.15 (s, 2H), 4.15 (t, J=8.5 Hz, 2H), 3.19 (t, J=8.6 Hz, 2H), 2.17 (s, 3H); MS(ESI+) m/z 321.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was triturated with CH2Cl2

Sources & evidence

ORD record
ord-b0d5468cb33249cfb1bb24c3064d951f
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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