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Potassium Carbonate → 4-[4-(6-Fluoro-benzo[b]thiophen-3yl)-[1,4]diazapan-1-yl]butyronitrile

HRID 1986907
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HRID 1986907 반응식
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]([N:16]3[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:14][S:13][C:12]=2[CH:23]=1.Br[CH2:25][CH2:26][CH2:27][C:28]#[N:29]>C(#N)C>[F:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]([N:16]3[CH2:22][CH2:21][CH2:20][N:19]([CH2:25][CH2:26][CH2:27][C:28]#[N:29])[CH2:18][CH2:17]3)=[CH:14][S:13][C:12]=2[CH:23]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 231124871-(6-Fluoro-benzo[b]thiophen-3-yl)-[1,4]diazepane

생성물 1

HCID 577225594-[4-(6-Fluoro-benzo[b]thiophen-3yl)-[1,4]diazapan-1-yl]butyronitrile수율 42.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Add potassium carbonate (39.3 g, 284 mmol) to a solution of 1-(6-fluoro-benzo[b]thiophen-3-yl)-[1,4]diazepane (Example 4) (23.7 g, 95 mmol) and 4-bromobutyronitrile (21.0 g, 142 mmol) in acetonitrile (400 mL) and stir the mixture under reflux for 10 h. Filter the mixture, evaporate the solvent, and dissolve the residue in ethyl acetate (EtOAc). Wash with water and saturated sodium chloride solution, and dry the organic phase over MgSO4. Evaporate the solvent under vacuum, and purify the crude product by column chromatography (EtOAc/MeOH 9:1) to give 12.9 g of a yellow oil LC/MS, (LiChrospher 5μ, RP-18, 250 mm

후처리

  1. temperatureunder reflux for 10 h
  2. filtrationFilter the mixture
  3. customevaporate the solvent
  4. dissolutiondissolve the residue in ethyl acetate (EtOAc)
  5. washWash with water and saturated sodium chloride solution
  6. dry with materialdry the organic phase over MgSO4
  7. customEvaporate the solvent under vacuum
  8. custompurify the crude product by column chromatography (EtOAc/MeOH 9:1)

출처 및 근거

ORD 기록
ord-425816799d0c42dd937dc897a4c7406c
출처 데이터셋
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07550469B2

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