Water → 7-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde

HRID 1797077노트

반응식

HRID 1797077 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[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[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[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[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 111841947-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine

생성물 1

HCID 221748437-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N,N-Dimethylformamide (100 mL) was cooled to 0° C. and treated with phosphorous oxychloride (5.7 mL, 60.8 mmol). After the addition was complete, the mixture was warmed to room temperature and stirred for 1 hour. To this was added 7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine (10.0 g, 40.5 mmol) and the resultant solution was stirred overnight. Water was added, followed by dichloromethane. The aqueous layer was extracted with dichloromethane. The combined organics were washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was recrystallized from diethyl ether and hexanes to give 7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (10.6 g, 95%) as a fluffy white solid. 1H NMR (CDCl3): δ 10.07 (s, 1 H), 8.37 (d, 1 H), 7.78 (m, 2 H), 7.48 (t, 1 H), 7.20 (m, 3 H); 19F NMR (CDCl3) δ −111.25; MS m/z 275 (M+1); Anal. Calcd for C14H8ClFN2O: C, 61.22; H, 2.94; N, 10.20. Found: C, 61.34; H, 2.90; N, 10.15; mp 212–213° C. (decomp.).

후처리

  1. additionAfter the addition
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washThe combined organics were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was recrystallized from diethyl ether and hexanes

출처 및 근거

ORD 기록
ord-f82e0e678dcb48099af6bd42ee0ab3ed
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07034030B2

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