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

HRID 238267

反応式

HRID 238267 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1a6eb3fef2f14ed88af10f8a85558141
出典データセット
uspto-grants-2014_02
特許番号
US08642621B2

関連ノート

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