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

HRID 887791Notes

Reaction equation

Br[C:2]1[C:10]([Cl: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>[Cl: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-chloro-2-methyl-2H-indazole-4-carboxylate (330 mg, 1.09 mmol), palladium acetate (24.5 mg, 0.109 mmol), triphenylphosphine (57.2 mg, 0.218 mmol), potassium carbonate (226 g, 1.64 mmol) and methyl acrylate (147 μL, 1.64 mmol) in N,N-dimethylformamide (11 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=30/70→60/40) to give the title compound (270 mg, yield 80%).

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=30/70→60/40)

Sources & evidence

ORD record: ord-152b9d9851ad47389f415d786cc4d647
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247429B2

Reaction notes

Loading…