Formic Acid → HCID 22008819, compound

HRID 322000Notes

Reaction equation

HRID 322000 reaction equation
Br[C:2]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([N:6]1[CH:11]=[CH:10][C:9](=[O:12])[CH2:8]C1)=O.C(N(CC)CC)C.[CH:25]([OH:27])=O>CN(C=O)C.C(O[Pd]OC(=O)C)(=O)C.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>[Cl:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:3]2[C:2]=1[C:25](=[O:27])[N:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH:4]12

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 22008820HCID 22008820, compound

Product 1

HCID 22008819HCID 22008819, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 84538Palladium(2+) acetate--triphenylphosphane (1/2/2)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(2-bromo-chlorobenzoyl)-2,3-dihydro-4-pyridinone (Preparation 3) (300 mg, 0.954 mmol), triethylamine (0.39 mmol, 0.54 ml), formic acid (0.05 ml, 1.3 mmol) and di(triphenylphosphine) diacetoxypalladium (47 mg, 0.063 mmol) in DMF (3 ml) was heated to 80° C. for 2 h. The cooled solution was filtered through celite, diluted with water, extracted twice with ethyl acetate, the extracts dried over sodium sulphate and evaporated. The residue was purified by flash column chromatography on silica eluting with 50% ethyl acetate in hexane to yield the title compound as a colourless oil (70 mg). MS (+CI) m/z 235/237 [M+H]+.

Workup

  1. filtrationThe cooled solution was filtered through celite
  2. additiondiluted with water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialthe extracts dried over sodium sulphate
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica eluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d095710205ce4149af120fea9605be03
Source dataset
uspto-grants-2001_04
Patent number
US06211189B1

Reaction notes

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