Triethylamine → HCID 68565220, compound

HRID 639305Notes

Reaction equation

HRID 639305 reaction equation
Br[C:2]1[N:3]=[C:4]([O:13][CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:5]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[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]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[C:4]([O:13][CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[N:3]=1)=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86619520HCID 86619520, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 68565220HCID 68565220, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.563 g (0.0017 mol) 5-bromo-3-cyclopentylmethoxy-2-pyrrolidin-1-yl-pyrazine in 4 mL methanol and 2 mL ethyl acetate was added 0.050 g PdCl2dppfCH2Cl2 and 0.48 mL (0.0035 mol) triethylamine and the mixture was stirred under an atmosphere of 70 bar carbon monoxide at 110° C. for 18 h in an autoclave. The solids were removed by filtration and the mother liquor was partitioned between water and ethyl acetate. The phases were separated and the organic phase was washed with water (2×) dried over sodium sulfate, evaporated and the residue was purified by chromatography on silica gel with dichloromethane:ethyl acetate=19:1 to yield 0.423 g of the title compound as slightly yellow orange crystals melting at 69-70° C.

Workup

  1. customThe solids were removed by filtration
  2. customthe mother liquor was partitioned between water and ethyl acetate
  3. customThe phases were separated
  4. washthe organic phase was washed with water (2×)
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customthe residue was purified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-2a64071349304adcb9a363ca07c0fece
Source dataset
uspto-grants-2010_04
Patent number
US07691863B2

Reaction notes

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