Dimethylformamide → 10a-(4-methoxyphenyl)-5-oxo-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]-pyrazine-8-carbonitrile

HRID 1753164노트

반응식

HRID 1753164 반응식
Br[C:2]1[N:6]2[CH2:7][C:8]3([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=4)[NH:14][CH2:13][CH2:12][N:9]3[C:10](=[O:11])[C:5]2=[CH:4][CH:3]=1.[CH3:23][N:24](C=O)C>[C-]#N.[Zn+2].[C-]#N>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:8]23[NH:14][CH2:13][CH2:12][N:9]2[C:10](=[O:11])[C:5]2[N:6]([C:2]([C:23]#[N:24])=[CH:3][CH:4]=2)[CH2:7]3)=[CH:16][CH:17]=1

참가 물질

4

반응물 2

HCID 6228DimethylformamideHCID 67369880HCID 67369880, 화합물

생성물 1

HCID 6736752410a-(4-methoxyphenyl)-5-oxo-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]-pyrazine-8-carbonitrile수율 71%

시약·촉매·용매 1

HCID 11186Zinc cyanide (Zn(CN)2)촉매

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온도
160 °C

실험 절차

8-bromo-10a-(4-methoxyphenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (50 mg, 0.14 mmol), zinc cyanide (24 mg, 0.20 mmol) and palladium(0) tetrakistriphenylphosphine (32 mg, 0.03 mmol) were suspended in dry DMF (2.5 mL) in a microwave vial flushed with argon. The mixture was heated in the microwave at 160° C. for 20 minutes. Water was added and the mixture extracted with CH2Cl2. The organic layers were dried (MgSO4), filtrated and concentrated in vacuo. The resulting residue was purified by flash chromatography (Biotage SP4 12 g cartridge, gradient 0-10% MeOH in CH2Cl2) to give 10a-(4-methoxyphenyl)-5-oxo-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazine-8-carbonitrile as a brown solid (45 mg, yield 71%) ESI-MI m/z [M+H]+ 309.1.

후처리

  1. customvial flushed with argon
  2. additionWater was added
  3. extractionthe mixture extracted with CH2Cl2
  4. dry with materialThe organic layers were dried (MgSO4)
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by flash chromatography (Biotage SP4 12 g cartridge, gradient 0-10% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-dc8cf21cf5cc41c4a41c0ba6ed8f671f
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163029B2

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