1-ethyl-2,3-dihydro-1H-indole-5-sulfonamide → 5-Bromo-1-ethylindoline-6-sulfonamide

HRID 528836Notes

Reaction equation

HRID 528836 reaction equation
C(N1C2C(=CC(S(N)(=O)=O)=CC=2)CC1)C.[C:16]([N:19]1[C:27]2[C:22](=[CH:23][C:24]([Br:32])=[C:25]([S:28]([NH2:31])(=[O:30])=[O:29])[CH:26]=2)[CH2:21][CH2:20]1)(=O)[CH3:17]>>[Br:32][C:24]1[CH:23]=[C:22]2[C:27](=[CH:26][C:25]=1[S:28]([NH2:31])(=[O:30])=[O:29])[N:19]([CH2:16][CH3:17])[CH2:20][CH2:21]2

Participants

3

Reactant 2

HCID 321037261-ethyl-2,3-dihydro-1H-indole-5-sulfonamideHCID 551511491-Acetyl-5-bromoindoline-6-sulfonamide2×

Product 1

HCID 867188845-Bromo-1-ethylindoline-6-sulfonamideYield 51.1%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 53, 1-acetyl-5-bromoindoline-6-sulfonamide (Intermediate 60A, 110 mg, 0.34 mmol) was converted to the title compound (53 mg, 50%). 1H NMR (DMSO-d6) δ 7.34 (s, 1H), 7.32 (s, 2H), 7.00 (s, 1H), 3.41 (t, J=8.5 Hz, 2H), 3.14 (q, J=7.1 Hz, 2H), 2.95 (t, J=8.5 Hz, 2H), 1.10 (t, J=7.2 Hz, 3H); MS(ESI+) m/z 307.1 (M+H)+.

Sources & evidence

ORD record
ord-69da3752e5994f19ad83234661095bfa
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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