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

HRID 475165Notes

Reaction equation

HRID 475165 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

HCID 86694713HCID 86694713, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-2c0f45ea40ad4f0387beee11373e21cf
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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