Potassium Carbonate → 3-Chloro-2-(3-chloro-pyrazol-1-YL)-pyridine

HRID 571659ノート

反応式

HRID 571659 の反応式
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:14]=[CH:13][NH:12][N:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:8][C:7]1[C:2]([N:12]2[CH:13]=[CH:14][C:10]([Cl:9])=[N:11]2)=[N:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 169882,3-DichloropyridineHCID 178478253HCID 178478253、化合物2 回

生成物 1

HCID 228315663-Chloro-2-(3-chloro-pyrazol-1-YL)-pyridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a mixture of 2,3-dichloropyridine (92.60 g, 0.629 mol) and 3-chloropyrazole (i.e. the product of Step B) (64.44 g, 0.629 mol) in N,N-dimethylformamide (400 mL) was added potassium carbonate (147.78 g, 1.06 mol), and the reaction mixture was then heated to 100° C. for 36 hours. The reaction mixture was cooled to room temperature and slowly poured into ice water. The precipitated solids were filtered and washed with water. The solid filter cake was taken up in ethyl acetate, dried over magnesium sulfate and concentrated. The crude solid was chromatographed on silica gel using 20% ethyl acetate/hexane as eluent to afford the title product as a white solid (39.75 g). 1H NMR (CDCl3) δ 6.43 (s, 1H), 7.26 (m, 1H), 7.90 (d, 1H), 8.09 (s, 1H), 8.41 (d, 1H).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe precipitated solids were filtered
  3. washwashed with water
  4. filtrationThe solid filter cake
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude solid was chromatographed on silica gel using 20% ethyl acetate/hexane as eluent

出典と根拠

ORDレコード
ord-3f45bb451874453caf54a94bd77f4aea
出典データセット
uspto-grants-2015_05
特許番号
US09029365B2

反応ノート

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