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

HRID 586372노트

반응식

HRID 586372 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-8ad0518c2cf24898b0c7b4a219712732
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936617B2

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