Ammonium Chloride → 7-(4'-Fluoro[1,1'-biphenyl]-3-yl)-6,7-dihydro-5h-pyrrolo[1,2-c]imidazol-7-ol

HRID 724221노트

반응식

HRID 724221 반응식
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1.[CH:20]1[N:24]=[CH:23][N:22]2[CH2:25][CH2:26][C:27](=[O:28])[C:21]=12.[Cl-].[NH4+]>CCCCCC.C1COCC1>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([C:27]3([OH:28])[C:21]4[N:22]([CH:23]=[N:24][CH:20]=4)[CH2:25][CH2:26]3)[CH:8]=2)=[CH:14][CH:15]=1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 27569773-Bromo-4'-fluorobiphenylHCID 111709605,6-Dihydropyrrolo[1,2-c]imidazol-7-oneHCID 178418339Butyllithium

생성물 1

HCID 97961407-(4'-Fluoro[1,1'-biphenyl]-3-yl)-6,7-dihydro-5h-pyrrolo[1,2-c]imidazol-7-ol수율 45.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

A solution (1.6 M; 1.98 ml) of n-butyl lithium in hexane was gently added dropwise to a solution of 3-bromo-4′-fluoro-1,1′-biphenyl (753 mg) in THF (10 ml) at −78° C., and the mixture was stirred at −78° C. for 30 min. A solution of 5,6-dihydro-7Hpyrrolo[1,2-c]imidazol-7-one (244 mg) in THF (10 ml) solution was gently added dropwise and the mixture was stirred at −78° C. for 1 h. A saturated aqueous ammonium chloride solution was added to the reaction mixture and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent, ethyl acetate→ethyl acetate:methanol=5:1) and recrystallized from acetone-hexane to give the title compound (265 mg) as colorless needle crystals.

후처리

  1. stirringthe mixture was stirred at −78° C. for 1 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent, ethyl acetate→ethyl acetate:methanol=5:1)
  7. customrecrystallized from acetone-hexane

출처 및 근거

ORD 기록
ord-6d5d550a3d10474193688d5d4178dcce
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141598B2

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