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Methanol → 5-Amino-6-(4-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid methyl ester

HRID 416471
Notes
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Reaction equation

HRID 416471 reaction equation
Br[C:2]1[N:3]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:5]([NH2:12])=[N:6][C:7]=1[C:8]([F:11])([F:10])[F:9].CO.[C:22]([O:25][CH2:26]C)(=[O:24])C.[C]=O>C(N(CC)CC)C>[CH3:26][O:25][C:22]([C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[N:6][C:5]([NH2:12])=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:3]=1)=[O:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 866347035-Bromo-3-(4-chloro-phenyl)-6-trifluoromethyl-pyrazin-2-ylamineHCID 178418416HCID 178418416, compound

Product 1

HCID 666225955-Amino-6-(4-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8471
Triethylamine
Solvent

Procedure

A mixture of 12.57 g 5-bromo-3-(4-chloro-phenyl)-6-trifluoromethyl-pyrazin-2-ylamine, 0.60 g palladium(II)chloride-dppf-dichloromethane complex, 75 ml methanol, 75 ml ethyl acetate and 10.0 ml triethylamine was heated to 110° C. in an autoclav under 70 bar of carbon monoxide for 20 h. The solvents were evaporated and the residue was purified by chromatography on silica gel with dichloromethane to yield 6.48 g of the title compound as off white solid. MS (M−H) at 330.1.

Workup

  1. customThe solvents were evaporated
  2. customthe residue was purified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-7d190378fde043ddac389aae374f20d3
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08088920B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes