Chloride → HCID 67703741, compound

HRID 55291Notes

Reaction equation

HRID 55291 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9](I)[C:8]([O:12][CH3:13])=[CH:7][CH:6]=1)=[O:4].[CH3:14][O:15][C:16](=[O:19])[CH:17]=[CH2:18].[Cl-].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:14][O:15][C:16](=[O:19])/[CH:17]=[CH:18]/[C:9]1[C:8]([O:12][CH3:13])=[CH:7][CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[N:10]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 49766559Methyl 6-iodo-5-methoxypicolinate

Product 1

HCID 67703741HCID 67703741, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

Under the conditions of example 1 B, a solution of 22 g of 2-iodo-3-methoxypyridine-6-carboxylic acid methyl ester in 50 ml of dimethylformamide is reacted with 12.6 g of acrylic acid methyl ester in the presence of 5.3 g of bis-triphenylphosphinepalladium(II) chloride, 25.9 g of potassium carbonate and 23.4 g of tetrabutylammonium bromide, worked up, and the crude product is chromatographed on silica gel with hexane/0-30% ethyl acetate. 11 g of 3-(3-methoxy-6-methoxycarbonyl-2-pyridyl)-(2E)-2-propenoic acid methyl ester of melting point 123°-126° C. is obtained.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-30% ethyl acetate

Sources & evidence

ORD record
ord-875e44878e014bf1b62a0846eeac75c5
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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