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

HRID 586374

反応式

HRID 586374 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒2 回HCID 31374Dimethylacetamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8d638e36cfbd4aaab052ecb27541dd34
出典データセット
uspto-grants-2005_08
特許番号
US06936617B2

関連ノート

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