Sodium hydride → 2-(4,5-Difluoro-2-nitro-phenylamino)-benzo[b]thiophene-3-carbonitrile

HRID 131376

반응식

HRID 131376 반응식
[NH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]#[N:12].F[C:14]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=1[N+:22]([O-:24])=[O:23].[H-].[Na+]>C1COCC1>[F:21][C:17]1[C:18]([F:20])=[CH:19][C:14]([NH:1][C:2]2[S:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[C:3]=2[C:11]#[N:12])=[C:15]([N+:22]([O-:24])=[O:23])[CH:16]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 750121,2,4-Trifluoro-5-nitrobenzeneHCID 232735812-Amino-1-benzothiophene-3-carbonitrile

생성물 1

HCID 184222662-(4,5-Difluoro-2-nitro-phenylamino)-benzo[b]thiophene-3-carbonitrile수율 22.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Combine 2-amino-benzo[b]thiophene-3-carbonitrile (3.93 g, 22.6 mmol), 2,4,5-trifluoro-nitrobenzene (4.0 g, 22.6 mmol) in 30 mL of THF, add sodium hydride (3.54 g, 88.5 mmol)) portionwise at 0˜5° C., after addition, the reaction stir overnight at RT, Pour the rection on ice water (200 mL), extract with dichloromethane (3×50 mL), the combined organic layer wash with water and brine, dry over Na2SO4. Concentrate down to a residue, purify by chromatography, gradient hexanes to hexane:CH2Cl2: EtOAc=5:5:0.5, obtain red orange solid 1.71 g as the title compound. 1H NMR (300 MHz, DMSO-d6): δ 10.34 (br, 1H), 8.41-8.35 (m, 1H), 7.96-7.94 (m, 1H), 7.85-7.79 (m, 1H), 7.64-7.61 (m, 1H), 7.52-7.49 (m, 1H), 7.42-7.36 (m, 1H).

후처리

  1. additionafter addition
  2. additionPour the rection on ice water (200 mL)
  3. extractionextract with dichloromethane (3×50 mL)
  4. washthe combined organic layer wash with water and brine
  5. dry with materialdry over Na2SO4
  6. concentrationConcentrate down to a residue
  7. custompurify by chromatography, gradient hexanes to hexane

출처 및 근거

ORD 기록
ord-64adf720ae0c44cd8666c28b7ddd9a6a
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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