Sodium hydride → HCID 67485570, 화합물

HRID 1511042노트

반응식

HRID 1511042 반응식
[CH2:1]([C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].[H-].[Na+].Br[C:13]1[CH:14]=[C:15]([N+]([O-])=O)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[SH:30]>CN(C=O)C.O>[CH2:1]([C:3]1[C:8]([O:9][C:15]2[C:16]([C:19]#[N:20])=[N:17][CH:18]=[C:13]([S:30][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=3)[CH:14]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

참가 물질

7

반응물 4

HCID 24758Sodium hydride2회HCID 27696985-Bromo-3-nitropyridine-2-carbonitrileHCID 38372322-Ethylpyridin-3-olHCID 178418616HCID 178418616, 화합물

생성물 1

HCID 67485570HCID 67485570, 화합물수율 58%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-ethylpyridin-3-ol (2.5 g, 20.3 mmol) in DMF (20 ml) at 0° C. was added sodium hydride (0.512 g, 21.3 mmol). After 15 minutes, 5-bromo-3-nitropicolinonitrile (4.63 g, 20.3 mmol) was added and the mixture was allows to warm slowly to ambient temperature and stirred for 2 hours. Pridine-2-thiol (0.804 g, 7.23 mmol) was added followed by sodium hydride (0.182 g, 7.60 mmol) and the mixture was stirred at ambient temperature overnight. Water (200 ml) was added and the mixture was extracted with diethyl ether (3×100 mL), washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified over silica gel (25 to 75% EtOAc in Hexanes) to afford 3-(2-ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile (1.4 g, 4.19 mmol).

후처리

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. extractionthe mixture was extracted with diethyl ether (3×100 mL)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified over silica gel (25 to 75% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-10f083994ec64f1db97d7d6e72f74cb2
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08212045B2

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