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

HRID 2100664

반응식

HRID 2100664 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

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

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ba3598acb7104e6bb407b1de0f1fbc2d
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572811B2

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