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

HRID 57961ノート

反応式

HRID 57961 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-85d3b572cb67465e9add09c7c5801774
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

反応ノート

読み込み中…