Dichloromethane → HCID 67504874, compound

HRID 1159219Notes

Reaction equation

HRID 1159219 reaction equation
Br[C:2]1[N:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:5]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[C:20]([O:23][CH2:24]C)(=[O:22])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>[CH3:24][O:23][C:20]([C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[N:3]=1)=[O:22]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 86619567HCID 86619567, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 67504874HCID 67504874, compound

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 5-bromo-3-(2-chloro-phenyl)-2-pyrrolidin-1-yl-pyrazine (0.25 g) in 7 ml methanol was added 2 ml ethyl acetate, 0.035 g [1,1′-bis(diphenylphosphino)-ferrocen]palladium(II)chloride 1:1 complex with dichloromethane and 0.25 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=2:1 to yield 0.15 g of the title compound as off-white foam, MS (ISP) 318.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-1a0eb0f9178a4183b5777a9d14322ecd
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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