Thionyl Chloride → 2-Chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine

HRID 586372ノート

反応式

HRID 586372 の反応式
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]2[C:15]=1[CH2:16][CH2:17][CH3:18]>C(Cl)Cl.CCOC(C)=O>[Cl:3][CH2:6][C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]2[C:15]=1[CH2:16][CH2:17][CH3:18]

参加物

5

反応物 2

HCID 24386Thionyl ChlorideHCID 223350472-Hydroxymethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine

生成物 1

HCID 223350602-Chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Thionyl chloride (125 mg, 1.06 mmol) is added to a solution of 2-hydroxymethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine (100 mg, 0.53 mmol) in CH2Cl2 (3 mL) at 0° C. under nitrogen with magnetic stirring. After 1 hour, the reaction is diluted with EtOAc (20 mL), washed with saturated aqueous NaHCO3 (10 mL), water (10 mL) and brine (10 mL). The solution is then dried over anhydrous sodium sulfate, filtered and evaporated at reduced pressure to obtain 2-chloromethyl-3-(1-propyl)-imidazolo[1,2-a]pyridine as a colorless oil. TLC (10% MeOH/CH2Cl2) Rf=0.60. Step 5. Preparation of 3-{1-[(3-propylimidazo[1,2-a]pyridin-2-yl)methyl]-1H-imidazol-2-yl}benzonitrile

後処理

  1. washwashed with saturated aqueous NaHCO3 (10 mL), water (10 mL) and brine (10 mL)
  2. dry with materialThe solution is then dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated at reduced pressure

出典と根拠

ORDレコード
ord-8ad0518c2cf24898b0c7b4a219712732
出典データセット
uspto-grants-2005_08
特許番号
US06936617B2

反応ノート

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