Triethylamine → HCID 68799100, compound

HRID 1865882Notes

Reaction equation

HRID 1865882 reaction equation
Br[C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[C]=O.[C:29]([O:32][CH2:33]C)(=[O:31])C>CO>[CH3:33][O:32][C:29]([C:2]1[CH:7]=[N:6][C:5]([NH2:8])=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[N:3]=1)=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86616967HCID 86616967, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 68799100HCID 68799100, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 10.20 g (0.029 mol) 5-bromo-3-(4-trifluoromethoxy-phenyl)-pyrazin-2-ylamine in 100 ml methanol and 40 ml ethyl acetate was added 0.500 g (0.0006 mol) PdCl2 dppf CH2Cl2 ([1,1′-Bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct, Cas Registry No. [95464-05-4]) and 8.113 ml (5.9 g, 0.058 mol) triethylamine and the mixture was stirred at 110° C. under 70 bar carbon monoxide pressure for 4 h. The solvents were evaporated and the residue was purified by chromatography on silica gel with a gradient of 100% heptane to 100% ethyl acetate to yield 6.800 g (73% yield) of the title compound as off white crystalline solid. MS (ISP) (M+H+)=314.0.

Workup

  1. customThe solvents were evaporated
  2. customthe residue was purified by chromatography on silica gel with a gradient of 100% heptane to 100% ethyl acetate

Sources & evidence

ORD record
ord-b706abd63fa846debb30998eb89cb580
Source dataset
uspto-grants-2009_12
Patent number
US07629346B2

Reaction notes

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