Acetonitrile → 2-[3-(4'-fluorobiphenyl-2-ylmethyl)-3H-imidazol-4-yl]ethanol

HRID 1877947노트

반응식

HRID 1877947 반응식
C([N:20]1[CH:24]=[C:23]([CH2:25][CH2:26][OH:27])[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C.Br[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1>C(Cl)Cl>[F:45][C:42]1[CH:43]=[CH:44][C:39]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH2:32][N:22]2[C:23]([CH2:25][CH2:26][OH:27])=[CH:24][N:20]=[CH:21]2)=[CH:40][CH:41]=1

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 106894902-(1-Trityl-1H-imidazol-4-yl)ethanolHCID 114484672-Bromomethyl-4'-fluorobiphenyl

생성물 1

HCID 668864042-[3-(4'-fluorobiphenyl-2-ylmethyl)-3H-imidazol-4-yl]ethanol

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of 2-(1-trityl-1H-imidazol-4-yl)ethanol (0.65 g, 1.80 mmol), acetonitrile (9 mL) and CH2Cl2 (12 mL) is added a solution of 2-bromomethyl-4′-fluorobiphenyl (0.478 g, 1.80 mmol) in CH2Cl2 (2 mL). The resulting mixture is stirred at room temperature overnight. The solution is concentrated and the residue is taken up in MeOH and heated to 75° C. for 3.5 h. The solution is then concentrated and the residue is partitioned between CH2Cl2 and aqueous 5% NaHCO3. The aqueous layer is then extracted with CH2Cl2 (3×). The combined organic layers are then washed with brine and dried over Na2SO4. The residue is then purified by flash chromatography (CH2Cl2/MeOH) give 2-[3-(4′-fluorobiphenyl-2-ylmethyl)-3H-imidazol-4-yl]ethanol. MS (ESI) m/z 297.1 (M+H).

후처리

  1. concentrationThe solution is concentrated
  2. temperatureheated to 75° C. for 3.5 h
  3. concentrationThe solution is then concentrated
  4. customthe residue is partitioned between CH2Cl2 and aqueous 5% NaHCO3
  5. extractionThe aqueous layer is then extracted with CH2Cl2 (3×)
  6. washThe combined organic layers are then washed with brine
  7. dry with materialdried over Na2SO4
  8. customThe residue is then purified by flash chromatography (CH2Cl2/MeOH)

출처 및 근거

ORD 기록
ord-37274ff09fda477eb8b518c2b9504db2
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314097B2

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