Phosphorus oxychloride → 2-Chloropyrazolo[1,5-a]pyridine

HRID 530030ノート

反応式

HRID 530030 の反応式
[N:1]1[N:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[CH:3][C:2]=1O.O=P(Cl)(Cl)[Cl:13]>>[Cl:13][C:2]1[CH:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[N:1]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178515341HCID 178515341、化合物

生成物 1

HCID 122844332-Chloropyrazolo[1,5-a]pyridine

実験手順

A stirred solution of pyrazolo[1,5-a]pyridin-2-ol (27-1; 0.9 g, 0.0067 mol) in POCl3 (10 mL) was heated in a sealed tube at 145° C. for 6 h. The reaction mixture was cooled to room temperature, poured into ice cold water (20 mL) and extracted with dichloromethane (3×20 mL). The combined organic layers were washed with saturated sodium chloride, dried over sodium sulphate and concentrated under vacuum to afford the crude compound, which was purified by column chromatography to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.36-8.34 (d, J=7.2 Hz, 1 H), 7.44-7.42 (d, J=9.2 Hz, 1 H), 7.17-7.13 (m, 1 H), 6.78-6.74 (m, 1 H), 6.43 (s, 1 H). MS (M+1): 152.8.

後処理

  1. extractionextracted with dichloromethane (3×20 mL)
  2. washThe combined organic layers were washed with saturated sodium chloride
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under vacuum
  5. customto afford the crude compound, which
  6. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-c5075422d4994c00b5a740a524b8be16
出典データセット
uspto-grants-2016_05
特許番号
US09351973B2

反応ノート

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