Water → 7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde

HRID 1269066노트

반응식

HRID 1269066 반응식
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[Cl:11][C:12]1[N:17]2[N:18]=[C:19]([C:21]3[O:22][CH:23]=[CH:24][C:25]=3[CH3:26])[CH:20]=[C:16]2[CH:15]=[CH:14][CH:13]=1.O>ClCCl>[Cl:11][C:12]1[N:17]2[N:18]=[C:19]([C:21]3[O:22][CH:23]=[CH:24][C:25]=3[CH3:26])[C:20]([CH:3]=[O:4])=[C:16]2[CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 184466337-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridine

생성물 1

HCID 184466327-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde수율 760%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A dry flask charged with dry N,N-dimethylformamide (100 mL) was treated with phosphorous oxychloride (8.8 mL, 94 mmol). The resultant solution was stirred at room temperature for 1 hour. 7-Chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridine (14.6 g, 63 mmol) was added and the reaction mixture was stirred for 2.5 hours. Water and dichloromethane were added to quench the reaction. The aqueous phase and organic phase were separated. The aqueous phase was extracted with dichloromethane. The organics were combined and washed with water, dried over magnesium sulfate, filtered and the filtrate was concentrated. Crystallization from a small amount of methanol gave 7-chloro-2-(3-methyl-2-furyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (12.4 g, 760%) as a peach color crystalline compound. 1H NMR (CDCl3): δ 10.58 (s, 1H), 8.43 (d, 1H), 7.58 (d, 1H), 7.48 (t, 1H), 7.21 (d, 1H), 6.51 (d, 1H), 2.56 (s, 3H). MS m/261 (M+1).

후처리

  1. customto quench
  2. customthe reaction
  3. customThe aqueous phase and organic phase were separated
  4. extractionThe aqueous phase was extracted with dichloromethane
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customCrystallization from a small amount of methanol

출처 및 근거

ORD 기록
ord-dc06c0c05c054162845f4f9f0c79fec4
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199120B2

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