Stannane, tributyl(1-ethoxyethenyl)- → HCID 86694713, 화합물

HRID 475165노트

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HRID 475165 반응식
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]

참가 물질

4

반응물 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 86694712HCID 86694712, 화합물

생성물 1

HCID 86694713HCID 86694713, 화합물수율 90.1%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
110 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-2c0f45ea40ad4f0387beee11373e21cf
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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