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

HRID 2415167ノート

反応式

HRID 2415167 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3b84e28124a0406f8caf8f62a0e66e56
出典データセット
uspto-grants-2004_11
特許番号
US06818644B1

反応ノート

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