Cesium carbonate → HCID 58913281、化合物

HRID 1910388ノート

反応式

HRID 1910388 の反応式
FC(F)(F)S(O[C:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH:12]=1)(=O)=O.[S:22]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23]1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[S:22]1[CH:26]=[CH:25][C:24]([C:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:11][CH:12]=2)=[CH:23]1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 581760Thiophene-3-boronic acidHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

生成物 1

HCID 58913281HCID 58913281、化合物収率 71.6%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a solution of tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (610 mg) in 1,2-dimethoxyethane (15 ml) was added 3-thienylboronic acid (353 mg), tetrakis(triphenylphosphine) palladium (106 mg) and aq. 2M cesium carbonate solution (2.7 ml) and the mixture was refluxed 2 hours under nitrogen atmosphere. After removal of solvent in vacuo, the residue was extracted by EtOAc. The extract was washed with brine, dried over MgSO4 and concentrated in vacuo. The resultant residue was purified by silica gel column (n-hexane:EtOAc=80:20) to give tert-butyl 4-(3-thienyl)-3,6-dihydropyridine-1(2H)-carboxylate (350 mg) as a colorless oil.

後処理

  1. temperaturethe mixture was refluxed 2 hours under nitrogen atmosphere
  2. customAfter removal of solvent in vacuo
  3. extractionthe residue was extracted by EtOAc
  4. washThe extract was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by silica gel column (n-hexane:EtOAc=80:20)

出典と根拠

ORDレコード
ord-20d7266fbabb48f583524e5b5ba2df0e
出典データセット
uspto-grants-2013_12
特許番号
US08603975B2

反応ノート

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