Stannane, trimethylphenyl- → Ethyl 6-phenylnicotinate

HRID 842696

反応式

HRID 842696 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 11096332Ethyl 6-phenylnicotinate収率 46%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-66b0726e5dd443c1b89dd6a6d53587aa
出典データセット
uspto-grants-2002_04
特許番号
US06376490B1

関連ノート

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