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

HRID 1007370

反応式

HRID 1007370 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 31347Sulfolane溶媒

実験手順

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 (0.25 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)+.

後処理

  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%)

出典と根拠

ORDレコード
ord-873edf5c2d404bcfbdced83db5255cd9
出典データセット
uspto-grants-2004_09
特許番号
US06794403B2

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