Triethylamine → HCID 67396130, compound

HRID 869706Notes

Reaction equation

HRID 869706 reaction equation
FC(F)(F)S(O[C:7]1[N:8]=[C:9]2[CH2:17][CH2:16][CH2:15][O:14][C:10]2=[N:11][C:12]=1[CH3:13])(=O)=O.C(N(CC)CC)C.[C:27]([O:30][CH2:31][CH3:32])(=[O:29])C>CN(C)C(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:13][C:12]1[N:11]=[C:10]2[O:14][CH2:15][CH2:16][CH2:17][C:9]2=[N:8][C:7]=1[C:27]([O:30][CH2:31][CH3:32])=[O:29]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86674516HCID 86674516, compound

Product 1

HCID 67396130HCID 67396130, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 31374DimethylacetamideSolvent

Procedure

A solution of 3-methyl-7,8-dihydro-6H-pyrano[2,3-b]pyrazin-2-yl trifluoromethanesulfonate (298 mg, 1.00 mmol), palladium(II) acetate (11 mg, 0.0490 mmol), bis(diphenylphosphino)ferrocene (55 mg, 0.0992 mmol), and triethylamine (202 mg, 2.00 mmol) in N,N-dimethylacetamide (3.0 mL) was heated at 80° C. for 24 h under carbon monoxide. After being cooled to ambient temperature, the reaction mixture was diluted ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, filtrated and concentrated in vacuo. The crude was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 to ethyl acetate) to give ethyl 3-methyl-7,8-dihydro-6H-pyrano[2,3-b]pyrazine-2-carboxylate. MS (APCI): m/z 223 (M+H).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltrated
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 to ethyl acetate)

Sources & evidence

ORD record
ord-78240e8a838c4ce3b54a24077bc29fb2
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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