Stannane, trimethylphenyl- → Ethyl 6-phenylnicotinate

HRID 842696

반응식

HRID 842696 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 11096332Ethyl 6-phenylnicotinate수율 46%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-66b0726e5dd443c1b89dd6a6d53587aa
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06376490B1

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