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

HRID 271560

反応式

HRID 271560 の反応式
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]

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-61ffb66676194eb78c51d58eeeef3fb6
出典データセット
uspto-grants-2008_11
特許番号
US07452886B2

関連ノート

読み込み中…