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

HRID 2389272

반응식

HRID 2389272 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.C(=O)([O-])[O-].[Cs+].[Cs+].CNC1CCCCC1NC>[Cu]I.CN1CCCC1=O>[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 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 8171545-Bromopyridine-2-carbonitrile

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

A mixture of the 5-bromopyridine-2-carbonitrile (0.957 g, 5.23 mmol), tert-butyl piperazine-1-carboxylate (1.36 g, 7.32 mmol), cesium carbonate (3.41 g, 10.5 mmol), racemic N,N′-dimethylcyclohexane-1,2-diamine (0.074 g, 0.52 mmol), and copper(I) iodide (0.010 mg, 0.052 mmol) was stirred with 13.1 mL of 1-methylpyrrolidin-2-one and purged with a stream of nitrogen. The reaction was heated to 120° C. for 8 hours. The mixture was diluted with dichloromethane (20 mL) and washed with water (3×20 mL). The organic layer was dried over sodium sulfate, filtered, concentrated, and subjected to purified by silica gel chromatography eluting with 0-50% EtOAc in hexanes. Collection of product containing fractions and removal of solvent yielded to yield tert-butyl 4-(6-cyanopyridin-3-yl)piperazine-1-carboxylate.

후처리

  1. custompurged with a stream of nitrogen
  2. additionThe mixture was diluted with dichloromethane (20 mL)
  3. washwashed with water (3×20 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto purified by silica gel chromatography
  8. washeluting with 0-50% EtOAc in hexanes
  9. customCollection of product
  10. additioncontaining
  11. customfractions and removal of solvent
  12. customyielded

출처 및 근거

ORD 기록
ord-c9d12e60c76c40658aeafca1f092aea5
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273737B2

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