Tricyclohexylphosphine → 6-[1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridin-6-yl]-N-[(4-methoxyphenyl)methyl]pyrazin-2-amine

HRID 57961노트

반응식

HRID 57961 반응식
Br[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=[N:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:23]1[N:28]=[CH:27][C:26]2[CH:29]=[N:30][N:31]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[N:33]=3)[C:25]=2[CH:24]=1)CCC.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>CN(C)C(=O)C.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]>[F:38][C:34]1[N:33]=[C:32]([N:31]2[C:25]3[CH:24]=[C:23]([C:2]4[N:7]=[C:6]([NH:8][CH2:9][C:10]5[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=5)[CH:5]=[N:4][CH:3]=4)[N:28]=[CH:27][C:26]=3[CH:29]=[N:30]2)[CH:37]=[CH:36][CH:35]=1

참가 물질

6

반응물 3

HCID 75806TricyclohexylphosphineHCID 867071426-bromo-N-[(4-methoxyphenyl)methyl]pyrazin-2-amineHCID 86707144Tributyl-[1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridin-6-yl]stannane

생성물 1

HCID 867071436-[1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridin-6-yl]-N-[(4-methoxyphenyl)methyl]pyrazin-2-amine수율 74.5%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 31374Dimethylacetamide용매

반응 조건

온도
150 °C

실험 절차

A mixture of 6-bromo-N-[(4-methoxyphenyl)methyl]pyrazin-2-amine (0.9932 mmol; 768.8 mg), tributyl-[1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridin-6-yl]stannane (2.173 mmol; 1093 mg), tricyclohexylphosphine (0.1192 mmol; 33.42 mg) and Tris(dibenzylideneacetone)dipalladium (0) (0.04966 mmol; 45.47 mg) in N,N-Dimethylacetamide (15 mL) was purged with Argon for 1 min. The reaction mixture was sealed and heated at 150° C. under microwave for 45 min. The mixture was partitioned between EtOAc and water. The organic layer was concentrated and the residue was purified on silica eluted with 0 to 100% EtOAc in Heptane to afford 6-[1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridin-6-yl]-N-[(4-methoxyphenyl)methyl]pyrazin-2-amine (316.3 mg, 48%).

후처리

  1. customwas purged with Argon for 1 min
  2. customThe reaction mixture was sealed
  3. customThe mixture was partitioned between EtOAc and water
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified on silica
  6. washeluted with 0 to 100% EtOAc in Heptane

출처 및 근거

ORD 기록
ord-85d3b572cb67465e9add09c7c5801774
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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