3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol → HCID 10221872, compound

HRID 1766258Notes

Reaction equation

HRID 1766258 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[CH3:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([OH:28])[CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1.[OH-].[Na+]>C1COCC1>[CH3:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:28][S:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])(=[O:10])=[O:9])[CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 24383-(1-Methyl-4-piperidinyl)-1H-indol-5-olHCID 14798Sodium HydroxideHCID 1377612-Fluorobenzenesulphonyl chloride

Product 1

HCID 10221872HCID 10221872, compoundYield 115.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By a method similar to Example 31, using 2-fluorobenzenesulfonyl chloride (234 mg, 1.2 mmol) added dropwise to a solution of 3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole (231 mg, 1.0 mmol) in 0.2 N sodium hydroxide (5.5 mL, 1.1 mmol) and THF (5 mL) gave 448 mg of the title compound as a crystalline solid. The product was recrystallized from ethyl acetate/hexanes to give 320 mg (82%) of the title compound an off white powder: mp=180-182° C.; MS(m/e): 389 (M+1); Calculated for C20H21FN2O3S: Calcd: C, 61.84; H, 5.45; N, 7.21. Found: C, 61.83; H, 5.57; N, 7.26.

Sources & evidence

ORD record
ord-8a6160740d6f4dd39637d8e4d8c9b629
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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