Ethyl Propionate → HCID 57899240, compound

HRID 1802767Notes

Reaction equation

HRID 1802767 reaction equation
C(N(CC)CC)C.I[C:9]1[CH:14]=[N:13][CH:12]=[CH:11][N:10]=1.[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:16][CH3:17]>O1CCCC1.C(OCC)C.[Br-].[Zn+2].[Br-].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:20]([O:19][C:15](=[O:18])[C:16]#[C:17][C:9]1[CH:14]=[N:13][CH:12]=[CH:11][N:10]=1)[CH3:21]

Participants

8

Reactant 3

HCID 7749Ethyl PropionateHCID 8471TriethylamineHCID 642841Iodopyrazine

Product 1

HCID 57899240HCID 57899240, compoundYield 52%

Reagents, catalysts & solvents 4

HCID 10421208Zinc bromideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a dry solution of zinc bromide (6.49 g, 28.8 mmol) in tetrahydrofuran (60 mL) was added triethylamine (16 mL, 115.2 mmol), iodopyrazine (4.95 g, 24 mmol), ethyl proprionate (3.66 mL, 36 mmol) and tetrakis(triphenylphosphine) palladium (832 mg, 0.72 mmol). The reaction mixture was allowed to stir at ambient temperature for 16 h, diluted with diethyl ether, washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried with anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified via silica gel column chromatography (40% ethyl acetate in heptane) to yield the title compound as an orange oil (2.19 g, 52% yield). LCMS (m/z): 176.97 (M+).

Workup

  1. washwashed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via silica gel column chromatography (40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-e4b43616fc454edc8024b22d5bd27303
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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