2-Chloro-5-nitropyridine → HCID 67235239, 화합물

HRID 1505323노트

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HRID 1505323 반응식
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[CH3:3].CC([O-])(C)C.[K+].Cl[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=1>CS(C)=O>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:11][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=2)[CH:8]=[CH:9][CH:10]=1)[CH3:1]

참가 물질

5

반응물 3

HCID 783082-Chloro-5-nitropyridineHCID 2353733-(propan-2-yloxy)phenol2회HCID 23665647Potassium tert-butoxide

생성물 1

HCID 67235239HCID 67235239, 화합물수율 81.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
20 °C

실험 절차

To a solution of 3-[(1-methylethyl)oxy]phenol (Intermediate 27, 456 mg) in DMSO (8 mL) was added t-BuOK (336 mg, 3 mmol, Acros). The reaction mixture was stirred at 20° C. for 30 minutes. 2-chloro-5-nitropyridine (474 mg, 3 mmol, Aldrich) was added and the resulting mixture was stirred at 120° C. for 2 hours. The reaction mixture was cooled to room temperature, poured into ice-water (50 mL) and extracted with dichloromethane (3 times 50 mL). The combined organic layers were dried over sodium sulphate, filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with (PE:EtOAc=50:1) to afford the title compound as a light yellow solid (670 mg).

후처리

  1. stirringthe resulting mixture was stirred at 120° C. for 2 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with dichloromethane (3 times 50 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel eluting with (PE:EtOAc=50:1)

출처 및 근거

ORD 기록
ord-1a2912d2fcd04b9dbbe2532c5a604279
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216967B2

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