Dimethylacetamide → 4-(4-Aminobenzoyl)benzonitrile

HRID 926470

반응식

HRID 926470 반응식
CN1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)=[O:8])=[CH:5]N=C1.C1(P(C2CCCCC2)[C:25]2C=CC=C[C:26]=2[C:31]2[C:36](C(C)C)=CC(C(C)C)=C[C:32]=2C(C)C)CCCCC1.CC([N:55](C)C)=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Zn]>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]([C:6]2[CH:5]=[CH:36][C:31]([C:32]#[N:55])=[CH:26][CH:25]=2)=[O:8])=[CH:14][CH:13]=1

참가 물질

8

반응물 3

HCID 31374DimethylacetamideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86715600(1-Methyl-1H-imidazol-5-yl)(4-nitrophenyl)methanone2회

생성물 1

HCID 198022084-(4-Aminobenzoyl)benzonitrile

시약·촉매·용매 4

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 23994Zinc촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

A mixture containing (4-aminophenyl)(4-chlorophenyl)methanone (2.5 g, 11 mmol, Intermediate 16: step b), zinc cyanide (1.65 g, 14.0 mmol), tris(dibenzylideneacetone)dipalladium (692 mg, 0.755 mmol), zinc powder (141 mg, 2.16 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos, 371 mg, 0.755 mmol), and dimethylacetamide (54 mL, sparged with nitrogen for 45 minutes) was heated to 120° C. After 2 hours, the flask was allowed to cool to 23° C. The mixture was diluted with ethyl acetate (150 mL) and then filtered through Celite®. The filtrate was washed with saturated aqueous sodium chloride solution (2×100 mL). The organic phase was dried over sodium sulfate and then filtered. Silica gel (8 g) was added to the filtrate and the solvent was removed by rotary evaporation to afford a free-flowing powder. The powder was loaded onto a column of silica gel for purification. Elution with dichloromethane initially, grading to 5% methanol-dichloromethane provided the title compound as a solid.

후처리

  1. temperatureto cool to 23° C
  2. filtrationfiltered through Celite®
  3. washThe filtrate was washed with saturated aqueous sodium chloride solution (2×100 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. additionSilica gel (8 g) was added to the filtrate
  7. customthe solvent was removed by rotary evaporation
  8. customto afford a free-flowing powder
  9. customThe powder was loaded onto a column of silica gel for purification
  10. washElution with dichloromethane initially

출처 및 근거

ORD 기록
ord-981720d70fbb48f2848e2d08a4c622fd
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284308B2

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