Benzenesulfonyl chloride → 1-Benzenesulfonyl-5-fluoro-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester

HRID 60221ノート

反応式

HRID 60221 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([F:14])[CH:12]=2)[NH:7][C:6]=1[CH3:15])=[O:4].[OH-].[Na+].[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([F:14])[CH:12]=2)[N:7]([S:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:26])=[O:25])[C:6]=1[CH3:15])=[O:4]

参加物

6

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 58365050Methyl 5-fluoro-2-methyl-1H-pyrrolo[2,3-B]pyridine-3-carboxylate

生成物 1

HCID 583651851-Benzenesulfonyl-5-fluoro-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester収率 93%

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 6344Dichloromethane溶媒

反応条件

温度
2.5 °C

実験手順

A cooled (0-5° C.) suspension of 5-fluoro-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (9.0 g, 43.2 mmol), powdered sodium hydroxide (5.4 g, 133.9 mmol) and benzyltriethylammonium chloride (0.2 g, 0.86 mmol) in dichloromethane (100 mL) was treated over ca. 5 minutes with benzenesulfonyl chloride (9.5 g, 6.9 mL, 54.0 mmol). The reaction mixture was allowed to stir at 0-5° C. for 20 minutes then allowed to warm to ambient temperature and stirred for 24 hours. The solid was removed by filtration through celite and the cake washed with dichloromethane. The filtrate was evaporated and the resultant residue triturated with diethyl ether to afford the title compound as a cream solid (14.0 g, 93%). 1H NMR (400 MHz, CDCl3): 8.27 (dd, J=2.8, 1.1 Hz, 1H), 8.18-8.18 (m, 2H), 7.97 (dd, J=8.7, 2.8 Hz, 1H), 7.61-7.61 (m, 1H), 7.52-7.51 (m, 2H), 3.94 (s, 3H), 3.16 (s, 3H).

後処理

  1. temperatureA cooled
  2. temperatureto warm to ambient temperature
  3. stirringstirred for 24 hours
  4. customThe solid was removed by filtration through celite
  5. washthe cake washed with dichloromethane
  6. customThe filtrate was evaporated
  7. customthe resultant residue triturated with diethyl ether

出典と根拠

ORDレコード
ord-283fc5e95c444d55995fdda501c270ac
出典データセット
uspto-grants-2016_09
特許番号
US09440976B2

反応ノート

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