Chloride → 1-(2-(Phenylethynyl)pyridin-3-yl)ethanone

HRID 1402703노트

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HRID 1402703 반응식
[C:1]([C:4]1[C:5](Br)=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C.[Cl-]>CN(C=O)C.C(Cl)Cl>[C:11]1([C:17]#[C:18][C:5]2[C:4]([C:1](=[O:3])[CH3:2])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

7

반응물 4

HCID 312ChlorideHCID 10821PhenylacetyleneHCID 81531DiisopropylethylamineHCID 99903691-(2-Bromopyridin-3-yl)ethan-1-one

생성물 1

HCID 147130351-(2-(Phenylethynyl)pyridin-3-yl)ethanone

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
25 °C

실험 절차

66 mg 3-Acetyl-2-bromopyridine, 56 μL phenylacetylene, 170 μL DIPEA, 22.5 mg triphenylphosphinpalladium(II) chlorid, 3 mg Cu(I)I were suspended in 1 mL DMF under argon atmosphere and stirred for 16 h at 25° C. The mixture was diluted with DCM and extracted with diluted aq. NH3 and brine. The organic phase was concentrated and the mixture separated via flash chromatography (10 g SiO2, cyclohexane→cyclohexane/ethylacetate 70:30) to yield 40 mg 1-(2-(phenylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS: Rt=1.21 min (method E), M+H=222.

후처리

  1. extractionextracted with diluted aq. NH3 and brine
  2. concentrationThe organic phase was concentrated
  3. customthe mixture separated via flash chromatography (10 g SiO2, cyclohexane→cyclohexane/ethylacetate 70:30)

출처 및 근거

ORD 기록
ord-8a061502be2847f99efc0c4be2cee822
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912173B2

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