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

HRID 887783
Notes
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Reaction equation

HRID 887783 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 59145845methyl 5-bromo-6-fluoro-2-methyl-2H-indazole-4-carboxylate

Product 1

HCID 59145866methyl 6-fluoro-5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2-methyl-2H-indazole-4-carboxylateYield 88.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

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

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes