3,4-Difluorobenzoyl chloride → 1-(3,4-Difluorobenzoyl)indoline-5-sulfonamide

HRID 528829Notes

Reaction equation

HRID 528829 reaction equation
C1(C(N2C3C(=CC(S(N)(=O)=O)=CC=3)CC2)=O)CCCCC1.[NH:22]1[C:30]2[C:25](=[CH:26][C:27]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:28][CH:29]=2)[CH2:24][CH2:23]1.[F:35][C:36]1[CH:37]=[C:38]([CH:42]=[CH:43][C:44]=1[F:45])[C:39](Cl)=[O:40]>>[F:35][C:36]1[CH:37]=[C:38]([CH:42]=[CH:43][C:44]=1[F:45])[C:39]([N:22]1[C:30]2[C:25](=[CH:26][C:27]([S:31]([NH2:34])(=[O:32])=[O:33])=[CH:28][CH:29]=2)[CH2:24][CH2:23]1)=[O:40]

Participants

4

Reactant 3

HCID 27245193,4-Difluorobenzoyl chlorideHCID 80272522,3-dihydro-1H-indole-5-sulfonamide2×HCID 606987421-(Cyclohexanecarbonyl)indoline-5-sulfonamide

Product 1

HCID 710864401-(3,4-Difluorobenzoyl)indoline-5-sulfonamideYield 78.8%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 55, indoline-5-sulfonamide (Intermediate 54A, 90 mg, 0.45 mmol) and 3,4-difluorobenzoyl chloride (69 μL, 0.54 mmol) were converted to the title compound (120 mg, 78%). 1H NMR (DMSO-d6) δ 7.60-7.21 (m, 6H), 7.01 (s, 2H), 3.85 (t, J=8.6 Hz, 2H), 2.92 (t, J=8.6 Hz, 2H); MS(ESI+) m/z 338.9 (M+H)+.

Sources & evidence

ORD record
ord-c0045dcafec34760bf8796cbecb3c20c
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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