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Dimethylformamide → 4-(5-Methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzonitrile

HRID 717091
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HRID 717091 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:19])[C:11]3[C:16]([CH:17]=2)=[C:15]([CH3:18])[CH:14]=[CH:13][CH:12]=3)=[CH:4][CH:3]=1.[CH3:20][N:21](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:18][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[CH:17]=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:20]#[N:21])=[CH:3][CH:4]=1)[NH:9][C:10]2=[O:19]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 762845543-(4-Bromophenyl)-5-methyl-1(2h)-isoquinolinone

생성물 1

HCID 898129544-(5-Methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzonitrile수율 79%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

실험 절차

3-(4-Bromo-phenyl)-5-methyl-2H-isoquinolin-1-one (200 mg, 0.64 mmol), zinc cyanide (90 mg, 0.76 mmol) and tetrakis(triphenylphosphine)palladium(0) (74 mg, 0.064 mmol) were stirred in DMF (2.1 mL) and degassed with N2. The reaction mixtures were irradiated using a microwave (300 W, 180° C., 30 min). The reaction mixtures were combined and the resulting precipitate was filtered, washed with DMF and water and dried to give 4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzonitrile as a yellowish solid (718 mg, 79%) which was used in the next step without further purification.

후처리

  1. customdegassed with N2
  2. customThe reaction mixtures
  3. customwere irradiated
  4. customa microwave (300 W, 180° C., 30 min)
  5. customThe reaction mixtures
  6. filtrationthe resulting precipitate was filtered
  7. washwashed with DMF and water
  8. customdried

출처 및 근거

ORD 기록
ord-e1c5511e683f41ea9684beca2c6ba8ea
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09193689B2

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