Methyl iodide → HCID 11623273, 화합물

HRID 422299노트

반응식

HRID 422299 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][CH2:9][CH2:10][C:11]1[O:12][C:13]2[C:14](=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=2)[N:15]=1.CI.[C:23]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[CH3:23][O:20][C:16]1[C:14]2[N:15]=[C:11]([CH2:10][CH2:9][C:8]#[C:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[O:12][C:13]=2[CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11680534HCID 11680534, 화합물

생성물 1

HCID 11623273HCID 11623273, 화합물수율 47.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazol-4-ol (20 mg, 76 μmol, Example 70), methyl iodide (57 μL, 114 μmol) and K2CO3 (18 mg, 130 μmol) in DMF (2 mL) was stirred under reflux for 3 h. The reaction mixture was then allowed to cool to room temperature and was dissolved in DCM. The organic phase was washed with water, HCl 1N; saturated solution of NaHCO3, brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 10 mg (36 μmol, 47%) of 4-methoxy-2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazole as a brown solid.

후처리

  1. temperatureunder reflux for 3 h
  2. washThe organic phase was washed with water, HCl 1N
  3. dry with materialsaturated solution of NaHCO3, brine, dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1)

출처 및 근거

ORD 기록
ord-d85be23755e84283b0da0505076ac68c
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101637B2

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