Cesium carbonate → Tert-butyl 4-(6-fluoropyridin-3-yl)piperazine-1-carboxylate

HRID 271560

반응식

HRID 271560 반응식
Cl.[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].Br[C:16]1[CH:17]=[CH:18][C:19]([F:22])=[N:20][CH:21]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O.CCCCCC.O>[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:16]2[CH:21]=[N:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:3])[CH3:4]

참가 물질

10

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2755973Tert-butyl Piperazine-1-carboxylate HydrochlorideHCID 27831685-Bromo-2-fluoropyridine

생성물 1

HCID 59834735Tert-butyl 4-(6-fluoropyridin-3-yl)piperazine-1-carboxylate수율 43%

시약·촉매·용매 5

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A suspension of piperazine-1-carboxylic acid tert-butyl ester hydrochloride (0.75 mmol), 5-bromo-2-fluoropyridine (0.90 mmol), (R)-2,2′-bis(diphenylphosphino)-1, 1′-binaphthyl (0.038 mmol), palladium acetate (0.038 mmol) and cesium carbonate (1.8 mmol) in toluene is stirred at 80° C. for 7 h and then 100° C. for 4 h, and poured into water. The mixture is extracted with AcOEt. The organic layer is washed with water, dried over magnesium sulfate, and concentrated. The crude product is purified by silica gel column chromatography to give the product in 43% yield. Rf=0.61 (n-hexane:AcOEt=1:1)

후처리

  1. wait100° C. for 4 h
  2. extractionThe mixture is extracted with AcOEt
  3. washThe organic layer is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified by silica gel column chromatography
  7. customto give the product in 43% yield

출처 및 근거

ORD 기록
ord-61ffb66676194eb78c51d58eeeef3fb6
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452886B2

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