Cesium carbonate → HCID 58913281, 화합물

HRID 1910388노트

반응식

HRID 1910388 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 58913281HCID 58913281, 화합물수율 71.6%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-20d7266fbabb48f583524e5b5ba2df0e
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08603975B2

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