Stannane, trimethylphenyl- → Ethyl 6-phenylnicotinate

HRID 842696

Reaction equation

HRID 842696 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9](Br)=[N:10][CH:11]=1)=[O:5])[CH3:2].[C:13]1([Sn](C)(C)C)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Li+]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 123095Stannane, trimethylphenyl-HCID 433294Lithium ChlorideHCID 14784668Ethyl 6-bromonicotinate

Product 1

HCID 11096332Ethyl 6-phenylnicotinateYield 46%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromopyridine-5-carboxylic acid ethyl ester (see part (i)) (1.855 g, 8.065 mmol), phenyltrimethyl tin (3.89 g, 16.13 mmol), bis(triphenylphosphine)palladium(II) chloride (371 mg) and lithium chloride (1.03 g. 24. 195 mmol) in dry dimethylformamide (40 ml) was heated at 100° C. for 1.5 hours under nitrogen. After cooling the mixture was concentrated under reduced pressure and the residue purified by flash chromatography on silica gel eluting with hexane:ethyl acetate (10:1, by volume) to give the title compound (0.843 g, 46%) as a white solid.

Workup

  1. temperatureAfter cooling the mixture
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue purified by flash chromatography on silica gel eluting with hexane:ethyl acetate (10:1, by volume)

Sources & evidence

ORD record
ord-66b0726e5dd443c1b89dd6a6d53587aa
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Linked notes

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