Water → 6-(Tert-butylthio)methyl-pyridine-3-carbonitrile

HRID 1190967노트

반응식

HRID 1190967 반응식
Br[CH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.[CH3:11][C:12]([SH:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.C(Cl)Cl>[C:12]([S:15][CH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1)([CH3:14])([CH3:13])[CH3:11]

참가 물질

7

반응물 4

HCID 962WaterHCID 6387tert-Butyl mercaptanHCID 10796Cesium carbonateHCID 219277766-(Bromomethyl)pyridine-3-carbonitrile

생성물 1

HCID 584955036-(Tert-butylthio)methyl-pyridine-3-carbonitrile수율 76%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

Dissolve 6-bromomethyl-pyridine-3-carbonitrile (6.2 g, 31.4 mmol) in anhydrous DMF (60 mL) under nitrogen. Add tert-butylthiol (5.32 mL, 47.2 mmol) followed by cesium carbonate (15.3 g, 47.2 mmol) and stir the resulting suspension overnight. Dissolve the reaction mixture in DCM (200 mL) and add water (200 mL). Extract the aqueous phase with DCM (2×200 mL) and dry the combined organic extracts over MgSO4. Filter, add silica gel and concentrate the mixture in vacuo. Purify the residue by chromatography on silica gel (40 g) eluting with cyclohexane/EtOAc (98:2 to 65:35 gradient) to obtain the desired material as a yellow solid (4.92 g, 76%). MS (ES+) m/z: 207 (M+H)+.

후처리

  1. extractionExtract the aqueous phase with DCM (2×200 mL)
  2. dry with materialdry the combined organic extracts over MgSO4
  3. filtrationFilter
  4. additionadd silica gel
  5. concentrationconcentrate the mixture in vacuo
  6. customPurify the residue by chromatography on silica gel (40 g)
  7. washeluting with cyclohexane/EtOAc (98:2 to 65:35 gradient)

출처 및 근거

ORD 기록
ord-c31941f3b78f4f8c88108a028e0da764
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680091B2

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