Tributylvinyltin → Methyl 1-methyl-6-vinyl-1H-indazole-3-carboxylate

HRID 2280866Notes

Reaction equation

HRID 2280866 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]([O:14][CH3:15])=[O:13])=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[CH2:16]([Sn](CCCC)(CCCC)C=C)[CH2:17]CC>CN(C=O)C>[CH3:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([CH:16]=[CH2:17])[CH:10]=2)[C:6]([C:12]([O:14][CH3:15])=[O:13])=[N:7]1

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 46942338Methyl 6-bromo-1-methyl-1H-indazole-3-carboxylate

Product 1

HCID 89370565Methyl 1-methyl-6-vinyl-1H-indazole-3-carboxylateYield 109.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To the solution of methyl 6-bromo-1-methyl-1H-indazole-3-carboxylate (60 mg, 0.22 mmol) in DMF (10 mL), tributyl(vinyl)tin (99 μL, 0.34 mmol), Pd(Ph3)4 (11 mg, 9 μmol) was added. After the addition was completed, the mixture was stirred at 90° C. for 4 h under Ar. Then the solvent was removed under reduced pressure. Purification by CC afforded compound 9a (52 mg, 88%).

Workup

  1. additionAfter the addition
  2. customThen the solvent was removed under reduced pressure
  3. customPurification by CC

Sources & evidence

ORD record
ord-59c64011fcc44757aa24d73c3ef5ffb7
Source dataset
uspto-grants-2015_09
Patent number
US09139539B2

Reaction notes

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