Water → HCID 57792065, 화합물

HRID 889623노트

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HRID 889623 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH3:18])[C:3]=1[NH:19][C:20]([C:22]1[S:23][CH:24]=[C:25]([NH2:27])[CH:26]=1)=[O:21].[Br:28]N1C(=O)CCC1=O.O>O1CCCC1>[CH3:18][C:4]1[CH:5]=[C:6]([C:8]([F:17])([C:13]([F:14])([F:15])[F:16])[C:9]([F:11])([F:12])[F:10])[CH:7]=[C:2]([CH3:1])[C:3]=1[NH:19][C:20]([C:22]1[S:23][C:24]([Br:28])=[C:25]([NH2:27])[CH:26]=1)=[O:21]

참가 물질

5

반응물 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 57792047HCID 57792047, 화합물

생성물 1

HCID 57792065HCID 57792065, 화합물수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-amino-thiophene-2-carboxylic acid [2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-amide (360 mg, 0.87 mmol) (Example I3) in tetrahydrofuran (20 ml) was added N-bromosuccinimide (NBS) (155 mg, 0.87 mmol). The mixture was stirred at room temperature for 1.5 hours. Water (50 ml) was added and the organic phase was extracted twice with ethyl acetate (50 ml). The combined organic extracts were dried over sodium sulfate and the solvent evaporated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane) to give 5-bromo-4-amino-thiophene-2-carboxylic acid [2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-amide (343 mg; 80% yield); 1H-NMR (CDCl3, 400 MHz): 7.26 (s, 2H), 7.10 (s, 1H), 3.8 (s, 2H), 2.24 (s, 6H) ppm.

후처리

  1. extractionthe organic phase was extracted twice with ethyl acetate (50 ml)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. customthe solvent evaporated
  4. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-cd238f135ff14385a62e42a6f73d68d7
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252936B2

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