3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol → 2,6-difluorobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-ylester

HRID 1766260Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[S:9](Cl)(=[O:11])=[O:10].[CH3:13][N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([OH:29])[CH:27]=3)[NH:22][CH:21]=2)[CH2:16][CH2:15]1.[OH-].[Na+]>>[CH3:13][N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([O:29][S:9]([C:3]4[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])(=[O:11])=[O:10])[CH:27]=3)[NH:22][CH:21]=2)[CH2:16][CH2:15]1

Participants

Reactant 3

HCID 24383-(1-Methyl-4-piperidinyl)-1H-indol-5-ol

HCID 14798Sodium Hydroxide

HCID 27342712,6-Difluorobenzenesulfonyl chloride

Product 1

HCID 102947512,6-difluorobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-ylesterYield 98.4%

Procedure

By a method similar to Example 31, using 2,6-difluorobenzenesulfonyl chloride (256 mg, 1.2 mmol) and 3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole (231 mg, 1.0 mmol), and 0.2 N sodium hydroxide (5.5 mL, 1.1 mmol) gave 400 mg (98%) of the title compound as an off white powder were obtained. The product was recrystallized from ethyl acetate/methanol/hexanes: mp=214-215° C.; MS(m/e): 407 (M+1); Calculated for C20H20F2N2O3S: C, 59.10; H, 4.96; N, 6.89. Found: C, 59.07; H, 5.16; N, 6.73.

Sources & evidence

ORD record: ord-af196751dedc43b9b47750d5ace61fc5
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230011B2

Reaction notes

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