Hexane → 1-[1-(4-cyanophenyl)4-(4-fluorophenyl)butyl]-1H-imidazole

HRID 1737858노트

반응식

HRID 1737858 반응식
[C:1]([C:3]1[CH:14]=[CH:13][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].[Li]CCCC.CCCCCC.[F:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35]Br)=[CH:29][CH:28]=1.[Cl-].[NH4+]>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:7]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[CH2:35][CH2:34][CH2:33][C:30]2[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=2)=[CH:13][CH:14]=1)#[N:2]

참가 물질

7

반응물 5

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 12364494-(Imidazol-1-ylmethyl)benzonitrileHCID 147371331-(3-Bromopropyl)-4-fluorobenzeneHCID 178418339Butyllithium

생성물 1

HCID 99051151-[1-(4-cyanophenyl)4-(4-fluorophenyl)butyl]-1H-imidazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-70 °C

실험 절차

1-(4-cyanobenzyl)-imidazole (1 g, 0.0054 mol) is dissolved into dry tetrahydrofuran (30 ml) and cooled to -70° C. n-BuLi in hexane (0.0054 mol) is added dropwise into the reaction mixture. After stirring for additional 30 min at -70° C. 3-(4-fluorophenyl)propyl bromide (1.5 g, 0.0069 mol) in THF (10 ml) is added to the mixture and stirig is continued for 2 hours. Then the mixture is allowed to warm to room temperature. Saturted aqueous ammonium chloride solution is added to the mixture, shaked and then the layers are separated. THF-phase is dried and evaporated to dryness. The residue is crystalizd from isopropanol as hydrogen chloride salt. The filtrate is purified by flash chromatography.

후처리

  1. additionis added dropwise into the reaction mixture
  2. waitis continued for 2 hours
  3. temperatureto warm to room temperature
  4. customshaked and then the layers are separated
  5. dry with materialTHF-phase is dried
  6. customevaporated to dryness
  7. customThe filtrate is purified by flash chromatography

출처 및 근거

ORD 기록
ord-a37b8f5ca0db421ba5455d1607c863bc
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962495

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