Tetrahydrofuran → [2-(4-Isobutyl-3-trifluoromethyl-phenyl)-benzooxazol-6-yl]-methanol

HRID 2220273

반응식

HRID 2220273 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[C:15]([CH2:17][OH:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].[Br-].[CH2:24]([Zn+])[CH:25]([CH3:27])[CH3:26].C1COCC1>Cl>[CH2:24]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[C:15]([CH2:17][OH:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20])[CH:25]([CH3:27])[CH3:26]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 68453052{2-[4-Chloro-3-(trifluoromethyl)phenyl]-1,3-benzoxazol-6-yl}methanolHCID 178448254HCID 178448254, 화합물

생성물 1

HCID 68453276[2-(4-Isobutyl-3-trifluoromethyl-phenyl)-benzooxazol-6-yl]-methanol

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

반응 조건

온도
100 °C

실험 절차

A mixture of [2-(4-chloro-3-trifluoromethyl-phenyl)-benzooxazol-6-yl]-methanol (1 eq) and Pd(PBut3)2 (0.05 eq) is treated with isobutyl zinc bromide in THF (0.5 M, 3 eq). The resulting mixture is heated at 100° C. in microwave for 30 minutes. The reaction mixture is diluted with aqueous HCl (5%) and extracted with EtOAc. The organic solution is washed with brine and dried over Na2SO4. After concentration, the residue is purified by flash column chromatography (30% EtOAc in hexane) to give the desired intermediate [2-(4-isobutyl-3-trifluoromethyl-phenyl)-benzooxazol-6-yl]-methanol. MS: (ES+): 350.1 (M+1)+.

후처리

  1. extractionextracted with EtOAc
  2. washThe organic solution is washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration
  5. customthe residue is purified by flash column chromatography (30% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-7dfa2d220c9e4b939e22386d033ff832
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417065B2

연결된 노트

불러오는 중…