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

HRID 1269066ノート

反応式

HRID 1269066 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dc06c0c05c054162845f4f9f0c79fec4
出典データセット
uspto-grants-2007_04
特許番号
US07199120B2

反応ノート

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