2-(3-fluorophenyl)-1H-imidazole → 6-chloro-2-{[2-(3-fluorophenyl)-1H-imidazol-1-yl]methyl}-3-propylimidazo[1,2-a]pyridine

HRID 586374

반응식

HRID 586374 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:14][C:15]1[N:16]=[C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]2[C:24]=1[CH2:25][CH2:26][CH3:27].CO.C(Cl)Cl>CC(N(C)C)=O.CCOC(C)=O>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]2[N:18]([C:24]([CH2:25][CH2:26][CH3:27])=[C:15]([CH2:14][N:12]3[CH:11]=[CH:10][N:9]=[C:8]3[C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[N:16]=2)[CH:19]=1

참가 물질

6

반응물 3

HCID 3168162-(3-fluorophenyl)-1H-imidazoleHCID 21226129Dichloromethane methanolHCID 223351072-Chloromethyl-6-chloro-3-(1-propyl)-imidazolo[1,2-a]pyridine

생성물 1

HCID 223350846-chloro-2-{[2-(3-fluorophenyl)-1H-imidazol-1-yl]methyl}-3-propylimidazo[1,2-a]pyridine

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매2회HCID 31374Dimethylacetamide용매

반응 조건

온도
60 °C

실험 절차

Kt-BuO (0.69 mL of 1 M in THF, 0.69 mmol) is added to a solution of 3-fluoro-(1H-imidazol-2-yl)benzene (88 mg, 0.58 mmol) in anhydrous DMA (1 mL). After 15 minutes, 2-chloromethyl-6-chloro-3-(1-propyl)-imidazolo[1,2-a]pyridine (140 mg, 0.58 mmol) is added and the reaction mixture is stirred and heated at 60° C. for 15 minutes. The reaction mixture is diluted with EtOAc (10 mL), washed with water (3 mL), brine (3 mL), dried over Na2SO4, filtered and evaporated at reduced pressure to obtain a yellow solid. Sequential chromatography on silica gel eluting with EtOAc and then 5%MeOH/CH2Cl2 provides 6-chloro-2-{[2-(3-fluoropheny)-1H-imidazol-1-yl]methyl}-3-propylimidazo[1,2-a]pyridine as a cream-colored yellow solid. TLC (10% MeOH/CH2Cl2) Rf=0.35.

후처리

  1. washwashed with water (3 mL), brine (3 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated at reduced pressure
  5. customto obtain a yellow solid

출처 및 근거

ORD 기록
ord-8d638e36cfbd4aaab052ecb27541dd34
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936617B2

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