Methyl Acrylate → methyl 6-fluoro-5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2-methyl-2H-indazole-4-carboxylate

HRID 887783Notes

Reaction equation

Br[C:2]1[C:10]([F:11])=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:12])[N:7]=2)[C:3]=1[C:13]([O:15][CH3:16])=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:42]([O:46][CH3:47])(=[O:45])[CH:43]=[CH2:44]>CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:11][C:10]1[C:2](/[CH:44]=[CH:43]/[C:42]([O:46][CH3:47])=[O:45])=[C:3]([C:13]([O:15][CH3:16])=[O:14])[C:4]2[C:8]([CH:9]=1)=[N:7][N:6]([CH3:12])[CH:5]=2

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of methyl 5-bromo-6-fluoro-2-methyl-2H-indazole-4-carboxylate (503 mg, 1.75 mmol), palladium acetate (39.3 mg, 0.175 mmol), triphenylphosphine (91.8 mg, 0.350 mmol), potassium carbonate (266 mg, 1.93 mmol) and methyl acrylate (314 μL, 3.50 mmol) in N,N-dimethylformamide (8.8 mL) was stirred with heating at 100° C. for 1 hr. The reaction solution was diluted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→60/40) to give the title compound (452 mg, yield 88%).

Workup

washwashed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→60/40)

Sources & evidence

ORD record: ord-55b594ffb9254b3195191f6fdcb6cd8f
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247429B2

Reaction notes

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