3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol → 2,4-Difluorobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-yl ester

HRID 1766253

반응식

HRID 1766253 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][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+]>C1COCC1>[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[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=4[F:1])(=[O:11])=[O:10])[CH:27]=3)[NH:22][CH:21]=2)[CH2:16][CH2:15]1

참가 물질

5

반응물 3

HCID 24383-(1-Methyl-4-piperidinyl)-1H-indol-5-olHCID 14798Sodium HydroxideHCID 27342732,4-Difluorobenzenesulfonyl Chloride

생성물 1

HCID 102947522,4-Difluorobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-yl ester수율 100.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

By a method similar to Example 31, using 2,4-difluorobenzenesulfonyl chloride (463 mg, 2.2 mmol) was added to a solution of 3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole (418 mg, 1.8 mmol) in 0.2 N sodium hydroxide (10 mL, 2.0 mmol) and THF (5 mL) gave 735 mg of product. The crude product was recrystallized from ethyl acetate/hexanes to give 680 mg (92%) of white crystals: mp=163-164° C.; MS(m/e): 406 (M+); Calculated for C20H20F2N2O3S: C, 59.10; H, 4.96; N, 6.89. Found: C, 58.86; H, 4.94; N, 6.95.

출처 및 근거

ORD 기록
ord-3263906d8e394de4afb2f1f453bfbc69
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230011B2

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