Benzoyl chloride → 1-Benzoylindoline-5-sulfonamide

HRID 528828

Reaction equation

HRID 528828 reaction equation
[CH:1]1([C:7]([N:9]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C2C(=CC(S(N)(=O)=O)=CC=2)CC1.C(Cl)(=O)C1C=CC=CC=1>>[C:7]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 7412Benzoyl chlorideHCID 80272522,3-dihydro-1H-indole-5-sulfonamide2×HCID 606987421-(Cyclohexanecarbonyl)indoline-5-sulfonamide

Product 1

HCID 176811371-Benzoylindoline-5-sulfonamideYield 79%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 55, indoline-5-sulfonamide (Intermediate 54A, 100 mg, 0.50 mmol) and benzoyl chloride (64 μL, 0.56 mmol) were converted to the title compound (120 mg, 79%). 1H NMR (DMSO-d6) δ 7.70 (s, 1H), 7.65-7.60 (m, 3H), 7.57-7.49 (m, 4H), 7.24 (s, 2H), 4.07 (t, J=8.5 Hz, 2H), 3.15 (t, J=8.4 Hz, 2H); MS(ESI+) m/z 303.2 (M+H)+.

Sources & evidence

ORD record
ord-e980f2a76d114151a079ad587acb17b1
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Linked notes

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