Methyl Acrylate → methyl 5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2-methyl-2H-indazole-4-carboxylate

HRID 887742Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:41]([O:45][CH3:46])(=[O:44])[CH:42]=[CH2:43]>CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:46][O:45][C:41](=[O:44])/[CH:42]=[CH:43]/[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of methyl 5-bromo-2-methyl-2H-indazole-4-carboxylate (1.65 g, 6.18 mmol), palladium acetate (139 mg, 0.62 mmol), triphenylphosphine (325 mg, 1.24 mmol), potassium carbonate (1.28 g, 9.27 mmol) and methyl acrylate (834 μL, 9.27 mmol) in N,N-dimethylformamide (60 mL) was stirred with heating at 100° C. for 50 min. The reaction solution was diluted with water, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→70/30) to give the title compound (1.33 g, yield 78%).

Workup

extractionextracted with ethyl acetate
washwashed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→70/30)

Sources & evidence

ORD record: ord-85bc38418f6c4746a1fc2a176729ab42
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247429B2

Reaction notes

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