Dichloromethane → 5-Amino-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid methyl ester

HRID 1865874Notes

Reaction equation

HRID 1865874 reaction equation
Br[C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[C:16]([O:19][CH2:20]C)(=[O:18])C.ClCCl.[C]=O>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(N(CC)CC)C>[CH3:20][O:19][C:16]([C:2]1[CH:7]=[N:6][C:5]([NH2:8])=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[N:3]=1)=[O:18]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 714639895-Bromo-3-(4-fluorophenyl)pyrazin-2-amineHCID 178418416HCID 178418416, compound

Product 1

HCID 675046415-Amino-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1.87 g 5-bromo-3-(4-fluoro-phenyl)-pyrazin-2-ylamine in 35 ml methanol was added 15 ml ethyl acetate, 0.260 g [1,1′-bis(diphenylphosphino)ferrocen]palladium(II)chloride 1:1 complex with dichloromethane and 1.95 ml triethylamine and the mixture was stirred at 110° C. under 70 bar carbon monoxide for 18 h. The reaction mixture was evaporated and the residue was purified by chromatography on silica gel with heptane:ethyl acetate=1:1 to yield 1.26 g of the title compound as white crystals. MS (ISP) (M+H+)=248.3.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by chromatography on silica gel with heptane

Sources & evidence

ORD record
ord-7cf0b260aca9458588db973534923d84
Source dataset
uspto-grants-2009_12
Patent number
US07629346B2

Reaction notes

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