1-ethyl-2,3-dihydro-1H-indole-5-sulfonamide → 1-(2-(Phenylthio)ethyl)indoline-5-sulfonamide

HRID 528834Notes

Reaction equation

HRID 528834 reaction equation
C(N1C2C(=CC(S(N)(=O)=O)=CC=2)CC1)C.[C:16]1([S:22][CH2:23][C:24]([N:26]2[C:34]3[C:29](=[CH:30][C:31]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:32][CH:33]=3)[CH2:28][CH2:27]2)=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:16]1([S:22][CH2:23][CH2:24][N:26]2[C:34]3[C:29](=[CH:30][C:31]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:32][CH:33]=3)[CH2:28][CH2:27]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 321037261-ethyl-2,3-dihydro-1H-indole-5-sulfonamideHCID 710607121-(2-(Phenylthio)acetyl)indoline-5-sulfonamide2×

Product 1

HCID 710629851-(2-(Phenylthio)ethyl)indoline-5-sulfonamideYield 57%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 53, 1-(2-(phenylthio)acetyl)indoline-5-sulfonamide (Intermediate 66, 74 mg, 0.21 mmol) was converted to the title compound (40 mg, 52%) after purification using preparative HPLC. 1H NMR (DMSO-d6) δ 7.43-7.33 (m, 6H), 7.21 (t, J=7.2. Hz, 1H), 6.90 (s, 2H), 6.36 (d, J=8.4 Hz, 1H), 3.53 (t, J=8.6 Hz, 2H), 3.39 (t, J=6.8 Hz, 2H), 3.19 (t, J=6.9 Hz, 2H), 2.94 (t, J=8.6 Hz, 2H); MS(ESI+) m/z 335.1 (M+H)+.

Sources & evidence

ORD record
ord-9cb86ddd57574206b32e148a9581c2e2
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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