1-ethyl-2,3-dihydro-1H-indole-5-sulfonamide → 1-(3,4-Dichlorophenethyl)indoline-5-sulfonamide

HRID 528832Notes

Reaction equation

HRID 528832 reaction equation
C(N1C2C(=CC(S(N)(=O)=O)=CC=2)CC1)C.[Cl:16][C:17]1[CH:18]=[C:19]([CH2:24][C:25]([N:27]2[C:35]3[C:30](=[CH:31][C:32]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:33][CH:34]=3)[CH2:29][CH2:28]2)=O)[CH:20]=[CH:21][C:22]=1[Cl:23]>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:24][CH2:25][N:27]1[C:35]2[C:30](=[CH:31][C:32]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:33][CH:34]=2)[CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 321037261-ethyl-2,3-dihydro-1H-indole-5-sulfonamideHCID 710610531-(2-(3,4-Dichlorophenyl)acetyl)indoline-5-sulfonamide2×

Product 1

HCID 710861861-(3,4-Dichlorophenethyl)indoline-5-sulfonamideYield 66%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 53, 1-(2-(3,4-dichlorophenyl)acetyl)indoline-5-sulfonamide (Intermediate 64, 140 mg, 0.363 mmol) was converted to the title compound (89 mg, 66%) after purification using preparative HPLC. 1H NMR (DMSO-d6) δ 7.64-7.63 (m, 1H), 7.54 (d, J=8.1 Hz, 1H), 7.43 (dd, J=8.4, 2.0 Hz, 1H), 7.39 (d, J=1.5 Hz, 1H), 7.33 (dd, J=8.3 Hz, 2.1 Hz, 1H), 6.90 (s, 2H), 6.56 (d, J=8.4 Hz, 1H), 3.49 (t, J=8.7 Hz, 2H), 3.42-3.38 (m, 2H), 2.95 (t, J=8.5 Hz, 2H), 2.84 (t, J=7.5 Hz, 2H); MS(ESI+) m/z 371.0 (M+H)+.

Sources & evidence

ORD record
ord-7eee0e02ed6c4cfd876211ac4c276c5f
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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