tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(6-cyanopyridin-3-yl)piperazine-1-carboxylate

HRID 2100664

反応式

HRID 2100664 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:8]([C:5]1[N:6]=[CH:7][C:2]([N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)=[CH:3][CH:4]=1)#[N:9]

参加物

7

反応物 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 8171545-Bromopyridine-2-carbonitrileHCID 23676156Sodium t-butoxide

生成物 1

HCID 67030211Tert-butyl 4-(6-cyanopyridin-3-yl)piperazine-1-carboxylate

試薬・触媒・溶媒 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

5-Bromo-pyridine-2-carbonitrile (8 mmol), tert-butyl 1-piperazine-carboxylate (9.6 mmol), Pd(dppf)Cl2 (0.24 mmol), dppf (0.36 mmol) and sodium tert-butoxide (11.9 mmol) are mixed in toluene (12 mL) and purged with N2. The mixture is heated in a microwave reactor at 120° C. for 15 minutes, poured into saturated Na2CO3 solution and extracted with EtOAc. The combined extracts are washed with saturated aqueous NaCl and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (2:1 hexanes/EtOAc) to give tert-butyl 4-(6-cyano-pyridin-3-yl)-piperazine-1-carboxylate.

後処理

  1. custompurged with N2
  2. additionpoured into saturated Na2CO3 solution
  3. extractionextracted with EtOAc
  4. washThe combined extracts are washed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. customthe residue is purified by silica gel chromatography (2:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-ba3598acb7104e6bb407b1de0f1fbc2d
出典データセット
uspto-grants-2009_08
特許番号
US07572811B2

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