Sodium Hydroxide → 2,6-Difluorobenzenesulfonic acid 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1h-indol-5-yl ester

HRID 1766262

反応式

HRID 1766262 の反応式
[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][CH:18]=[C: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[CH2:15][CH:16]=[C: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)[CH2:18][CH2:19]1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 27342712,6-Difluorobenzenesulfonyl chlorideHCID 149732073-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-1H-indol-5-ol

生成物 1

HCID 102228832,6-Difluorobenzenesulfonic acid 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1h-indol-5-yl ester収率 28.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

By a method similar to Example 31, using a solution of 2,6-difluorobenzenesulfonyl chloride (380 mg, 1.79 mmol) in THF (5 mL) was added to a mixture of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-hydroxy-1H-indole (340 mg, 1.49 mmol) in 0.2 N sodium hydroxide (8.2 mL, 1.64 mmol) and THF (5 mL) gave 170 mg (28%) of homogeneous product as a tan solid. The product was crystallized from ethyl acetate to give 96 mg (16%) of the title compound as a yellow powder: mp 183° C. dec; MS(m/e): 405 (M+1), 403 (M−1); Calculated for C20H18F2N2O3S: C, 59.40; H, 4.49; N, 6.93. Found: C, 59.22; H, 4.24; N, 6.65.

出典と根拠

ORDレコード
ord-f1eda14f4d4a47628ec6d9026a31fc14
出典データセット
uspto-grants-2007_06
特許番号
US07230011B2

関連ノート

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