Ethyl Methacrylate → HCID 18449898, compound

HRID 1696571Notes

Reaction equation

HRID 1696571 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]([NH2:13])=[CH:11][C:10]([C:14]([CH3:17])([CH3:16])[CH3:15])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+].C([O:45][C:46](=[O:50])[C:47]([CH3:49])=[CH2:48])C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:13][C:12]1[N:8]([C:4]2[CH:3]=[C:2](/[CH:48]=[C:47](\[CH3:49])/[C:46]([OH:50])=[O:45])[CH:7]=[CH:6][CH:5]=2)[N:9]=[C:10]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:11]=1

Participants

7

Reactant 4

HCID 7343Ethyl MethacrylateHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 184498781-(3-Bromophenyl)-3-(tert-butyl)-1H-pyrazol-5-amine

Product 1

HCID 18449898HCID 18449898, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-(3-bromo-phenyl)-5-t-butyl-2H-pyrazol-3-ylamine (5.8 g, 20 mmol), Pd(OAc)2 (450 mg, 2 mmol), PPh3 (1.0 g, 4 mmol), and K2CO3 (5.5 g, 40 mmol) in DMF (50 mL) was added 2-methyl-acrylic acid ethyl ester (2.8 g, 25 mmol) at RT under N2. The mixture was stirred at 80° C. overnight, concentrated under reduced pressure, and purified by column chromatography to afford (E)-3-[3-(5-amino-3-t-butyl-1H-pyrazol-1-yl)phenyl]-2-methylacrylic acid (3.2 g). MS (ESI) m/z: 328 (M+H+)

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-d2cdfe3f2e6c410a8a61de847f7a9e9e
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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