Cesium carbonate → 1,1-Dimethylethyl 4-(2-cyanophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate

HRID 238267

반응식

HRID 238267 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11](OS(C(F)(F)F)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O)#[N:23].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:22]#[N:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 27346102-Cyanophenylboronic acidHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

생성물 1

HCID 183265921,1-Dimethylethyl 4-(2-cyanophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate수율 51.6%

시약·촉매·용매 2

HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
120 °C

실험 절차

4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.5 g, 1.5 mmol), 2-cyanophenylboronic acid (0.23 g, 1.6 mmol), tetrakis-triphenylphosphine (0.17 g, 0.15 mmol) and cesium carbonate (0.73 g, 2.26 mmol) were dissolved in a mixture of DME (3 mL), IMS (1.0 mL) and water (0.4 mL) under argon. The mixture was heated by microwave irradiation to 120° C. for 0.3 hours then diluted with water. The products were extracted into DCM, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 0-20% ethyl acetate/hexane. The fractions containing the desired product were concentrated under vacuum to give the title compound as a yellow oil (0.22 g). LCMS m/z 261.2 [M+H]+. R.T.=4.59 min (Analytical Method 4).

후처리

  1. extractionThe products were extracted into DCM
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent removed by evaporation under vacuum
  5. customThe residue was purified by flash chromatography on silica eluting with 0-20% ethyl acetate/hexane
  6. additionThe fractions containing the desired product
  7. concentrationwere concentrated under vacuum

출처 및 근거

ORD 기록
ord-1a6eb3fef2f14ed88af10f8a85558141
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642621B2

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