Diethyl Ether → 2-(1-(4-bromophenyl)-2-(2-(2-fluorophenyl)propan-2-yl)-1H-imidazol-4-yl)propan-2-ol

HRID 1916885노트

반응식

HRID 1916885 반응식
[CH3:1][Mg+].[Br-].[Br:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14](C(OCC)=O)[N:13]=[C:12]2[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])([CH3:23])[CH3:22])=[CH:7][CH:6]=1.ClCCl.CC[O:36][CH2:37][CH3:38]>>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:37]([OH:36])([CH3:38])[CH3:1])[N:13]=[C:12]2[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])([CH3:23])[CH3:22])=[CH:7][CH:6]=1

참가 물질

5

반응물 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 66797364ethyl 1-(4-bromophenyl)-2-(2-(2-fluorophenyl)propan-2-yl)-1H-imidazole-4-carboxylateHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 667973732-(1-(4-bromophenyl)-2-(2-(2-fluorophenyl)propan-2-yl)-1H-imidazol-4-yl)propan-2-ol수율 78%

반응 조건

온도
0 °C

실험 절차

To a 250 mL round bottom flask, purged with dry N2 and attached with addition funnel, was added a 3.0M MeMgBr (12 mL, 3.7 equiv) solution in Et2O. The flask was cooled to 0° C. prior to dropwise addition of ethyl 1-(4-bromophenyl)-2-(2-(2-fluorophenyl)propan-2-yl)-1H-imidazole-4-carboxylate (4.22 g, 9.78 mmol) in a solution of anhydrous dichloromethane (80 mL). The reaction solution was allowed to stir, warming to room temperature over 1 hr. The reaction solution was quenched by addition of aq NH4Cl. The mixture was poured to a reparatory funnel and the dichloromethane layer was partitioned, dried over Na2SO4, filtered, concentrated and chromatographed through a 40 g SiO2 column using a gradient of 100% Hx to 70% EtOAc to yield the title compound (3.19 g, 78% yield). LCMS (ES): m/z=417.3, 419.3 [M+H]+.

후처리

  1. customTo a 250 mL round bottom flask, purged with dry N2
  2. additionattached with addition funnel
  3. temperaturewarming to room temperature over 1 hr
  4. customThe reaction solution was quenched by addition of aq NH4Cl
  5. additionThe mixture was poured to a reparatory funnel
  6. customthe dichloromethane layer was partitioned
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customchromatographed through a 40 g SiO2 column

출처 및 근거

ORD 기록
ord-84ea08fb65af47a2aca49649b886d58e
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618154B2

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