Stannane, tributyl(1-ethoxyethenyl)- → HCID 86694713、化合物

HRID 475165ノート

反応式

HRID 475165 の反応式
Br[C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH3:12].C([Sn](CCCC)(CCCC)[C:18]([O:20][CH2:21][CH3:22])=[CH2:19])CCC>CN1C(=O)CCC1>[CH2:21]([O:20][C:18]([C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH3:12])=[CH2:19])[CH3:22]

参加物

4

反応物 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 86694712HCID 86694712、化合物

生成物 1

HCID 86694713HCID 86694713、化合物収率 90.1%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
110 °C

実験手順

To a mixture of 4-bromo-6-fluoro-1-methyl-1H-indazole (1.42 g, 6.25 mmol) and tributyl(1-ethoxyvinyl)stannane (2.74 mL, 8.13 mmol, 1.3 eq.) in NMP (24 mL) under an argon atmosphere was added Pd(0)(PPh3)4 (1.08 g, 0.94 mmol, 0.2 eq.). After the mixture was heated at 110° C. overnight, it was cooled and partitioned between EtOAc and water. The organic layer was washed with brine, dried (MgSO4), and evaporated in vacuo. The crude was purified by SiO2 chromatography eluting with hexane:ethyl acetate (3:1) to afford 4-(1-ethoxyvinyl)-6-fluoro-1-methyl-1H-indazole as a yellow oil (1.24 g, 90%). MS (ESI): m/z=221.3 [M+1]+.

後処理

  1. temperatureit was cooled
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe crude was purified by SiO2 chromatography
  7. washeluting with hexane:ethyl acetate (3:1)

出典と根拠

ORDレコード
ord-2c0f45ea40ad4f0387beee11373e21cf
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

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