Cesium fluoride → Tert-butyl 4-(6-phenylpyridin-2-yl)piperazine-1-carboxylate

HRID 2415167노트

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HRID 2415167 반응식
Br[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.[C:21]1(OB(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[F-].[Cs+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:21]1([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)[CH:5]=[CH:4][CH:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

8

반응물 4

HCID 25953Cesium fluorideHCID 78412Phenyl dihydrogen orthoborateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 160590464-Boc-1-(6-bromo-2-pyridyl)piperazine

생성물 1

HCID 68577637Tert-butyl 4-(6-phenylpyridin-2-yl)piperazine-1-carboxylate

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
50 °C

실험 절차

A mixture of 2 g (5.84 mmol) of tert.butyl 4-(6-bromo-pyridin-2-yl)-piperazine-1-carboxylate, 0.75 g (6.15 mmol) of phenylboric acid, 2.66 g (17.52 mmol) of caesium fluoride, 0.045 g (0.15 mmol) of 2-(di-t-butylphosphino)-biphenyl and 0.013 g (0.06 mmol) of palladium acetate in 20 ml of dioxane is stirred for six hours at 50° C. under nitrogen. Then it is diluted with water and the reaction mixture is extracted with ethyl acetate. The organic phase is separated off and dried over sodium sulphate. Purification is by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate=4:1).

후처리

  1. extractionthe reaction mixture is extracted with ethyl acetate
  2. customThe organic phase is separated off
  3. dry with materialdried over sodium sulphate
  4. customPurification

출처 및 근거

ORD 기록
ord-3b84e28124a0406f8caf8f62a0e66e56
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06818644B1

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