2,6-Difluorobenzenesulfonyl chloride → 2,6-difluorobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-ylester

HRID 1766264Notes

Reaction equation

HRID 1766264 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=3)[NH:10][CH:9]=2)=[CH:4][CH2:3]1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[S:26](Cl)(=[O:28])=[O:27]>CN(C)C=O.[H-].[Na+]>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][S:26]([C:20]4[C:21]([F:25])=[CH:22][CH:23]=[CH:24][C:19]=4[F:18])(=[O:28])=[O:27])[CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 27342712,6-Difluorobenzenesulfonyl chlorideHCID 179801143-(1-methylpyridin-4-yl)-5-hydroxy-1H-indole

Product 1

HCID 102947512,6-difluorobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-ylesterYield 51.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24758Sodium hydrideSolvent

Procedure

By a method similar to Example 45, using 3-(1-methyl-pyridin-4-yl)-5-hydroxy-1H-indole (1.50 g, 6.5 mmol) in dimethylformamide (40 mL), sodium hydride (0.29 g of a 60% dispersion in oil, 7.2 mmol), 2,6-difluorobenzenesulfonyl chloride (1.52 g, 7.2 mmol) provided 1.35 g (51%) of 2,6-difluorobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-ylester as an off-white solid: mp 235-238° C.; MS(ES+): m/e 407.0 (M+1); 1H NMR (400 MHz, dmso-d6): 11.04 (br s, 1H), 7.92-7.82 (m, 1H), 7.42-7.33 (m, 2H), 7.29 (d, 1H, J=8.8 Hz), 7.15 (d, 1H, J=2.0 Hz), 7.06 (d, 1H, J=2.0 Hz), 6.79 (dd, 1H, J=8.8, 1.8 Hz), 2.78 (br d, 2H, J=11.2 Hz), 2.56-2.46 (m, 1H), 2.16 (s, 3H), 1.93 (br t, 2H, J=11.8 Hz), 1.74-1.64 (m, 2H), 1.60-1.46 (m, 2H).

Sources & evidence

ORD record
ord-a3d5b980a90948929d9a844a7262bbbe
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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