1,3-Dibromo-5,5-dimethylhydantoin → 7-(2-Bromo-1-fluoroethyl)-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol

HRID 1247234

반응식

HRID 1247234 반응식
N1C=CC=CC=1.[FH:7].C([O:11][C:12]1[CH:13]=[C:14]([CH:32]=[CH2:33])[C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([O:26]C(=O)C)=[C:22]([F:30])[CH:21]=3)=[N:17][C:16]=2[CH:31]=1)(=O)C.[Br:34]N1C(C)(C)C(=O)N(Br)C1=O>S1(CCCC1)(=O)=O.Cl>[Br:34][CH2:33][CH:32]([C:14]1[C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([F:30])[CH:21]=3)=[N:17][C:16]=2[CH:31]=[C:12]([OH:11])[CH:13]=1)[F:7]

참가 물질

6

반응물 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 64774Pyridine, hydrofluoride (1:1)HCID 112682632-[4-(Acetyloxy)-3-fluorophenyl]-7-vinyl-1,3-benzoxazol-5-yl acetate

생성물 1

HCID 1363776577-(2-Bromo-1-fluoroethyl)-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 31347Sulfolane용매

실험 절차

Hydrogen fluoride pyridine (1.14 mL) was added dropwise into a cold (0° C.) solution of 2-[4-(acetyloxy)-3-fluorophenyl]-7-vinyl-1,3-benzoxazol-5-yl acetate (0.25 g, 0.7 mmol), in sulfolane (3 mL). The reaction mixture was stirred for 5 min and then 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (120 mg) was added in one portion. The mixture was stirred at room temperature for 24 h, diluted with HCl (1N) and extracted with EtOAc. The organic layer was dried over MgSO4. Evaporation and purification by flash chromatography (CH2Cl2/isopropyl alcohol 0.3%) gave 7-(2-bromo-1-fluoroethyl)-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol as a white solid (025 g, m.p. 185–186° C.). The product was taken in acetonitrile (2 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (150 mg) was added. The reaction mixture was stirred for 24 h, poured into cold (0° C.) HCl (1N, 10 mL) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (20% EtOAc/hexanes) gave a white solid (160 mg, m.p. 213–214° C.); MS m/e 290 (M+H)+.

후처리

  1. stirringThe mixture was stirred at room temperature for 24 h
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. customEvaporation and purification by flash chromatography (CH2Cl2/isopropyl alcohol 0.3%)

출처 및 근거

ORD 기록
ord-99cd426202e7432a891224308ead01f4
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129258B2

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