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

HRID 60221노트

반응식

HRID 60221 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 6344Dichloromethane용매

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온도
2.5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-283fc5e95c444d55995fdda501c270ac
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440976B2

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