Pyridine → 5-Benzyloxycarbonylamino-2-(2-methyl-imidazol-1-yl)fluorobenzene

HRID 1582337

반응식

HRID 1582337 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH3:14])=[C:6]([F:8])[CH:7]=1.N1C=CC=CC=1.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:25]([O:24][C:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH3:14])=[C:6]([F:8])[CH:7]=1)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 218766203-fluoro-4-(2-methyl-1H-imidazol-1-yl)aniline

생성물 1

HCID 218766515-Benzyloxycarbonylamino-2-(2-methyl-imidazol-1-yl)fluorobenzene수율 93.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5-Amino-2-(2-methylimidazol-1-yl)fluorobenzene (34.25 g, 0.179 M) was dissolved in dry dichloromethane (600 ml) under nitrogen, and cooled to −5°. Pyridine (17.7 g, 0.224 M) was added, followed by benzyl chloroformate (33.7 g, 0.197 M) over 20 minutes. The mixture was stirred and the temperature allowed to rise to ambient over 16 hours. Aqueous sodium bicarbonate (5%, 250 ml) was added, the organic layer separated, the aqueous layer re-extracted with dichloromethane (2×300 ml), and combined extracts dried (magnesium sulfate). After filtration and evaporation, the residue was recrystallised from toluene (400 ml) to give title product (54.5 g). NMR (DMSO-d6) δ: 2.13 (s, 3H); 5.18 (s, 2H); 6.89 (s, 1H); 7.17 (s, 1H); 7.41 (overlapping m, 7H); 7.73 (dd, 1H); 10.21 (br, 1H). MS (ESP): 326 (MH+) for C18H16FN3O2

후처리

  1. temperaturecooled to −5°
  2. customthe organic layer separated
  3. extractionthe aqueous layer re-extracted with dichloromethane (2×300 ml)
  4. dry with materialdried (magnesium sulfate)
  5. filtrationAfter filtration and evaporation
  6. customthe residue was recrystallised from toluene (400 ml)

출처 및 근거

ORD 기록
ord-71348f1e773d4121a09a5c5e9061104a
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734200B1

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