Sodium Nitrite → 4-chloro-7-methoxy-1H-pyrazolo[4,3-c]pyridine

HRID 69317ノート

反応式

HRID 69317 の反応式
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[C:11]([CH3:12])=[C:10]([NH2:13])[C:9]([O:14][CH3:15])=[CH:8][N:7]=1>O.C(O)(=O)C>[Cl:5][C:6]1[C:11]2[CH:12]=[N:1][NH:13][C:10]=2[C:9]([O:14][CH3:15])=[CH:8][N:7]=1

参加物

5

反応物 2

HCID 23668193Sodium NitriteHCID 867178172-Chloro-5-methoxy-3-methylpyridin-4-amine

生成物 1

HCID 867178184-chloro-7-methoxy-1H-pyrazolo[4,3-c]pyridine

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

A solution of sodium nitrite (98%, 326 mg, 4.63 mmol) in water (0.6 mL) was added to a solution of C4 (200 mg, 1.16 mmol) in acetic acid (8 mL), and the reaction mixture was heated at 75° C. for 1 hour. After the reaction mixture had cooled to room temperature, it was concentrated in vacuo, diluted with saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Silica gel chromatography (Gradient: 25% to 50% ethyl acetate in heptane) provided the product as a yellow solid. Yield: 140 mg, 0.763 mmol, 66%. LCMS m/z 184.0 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 8.17 (s, 1H), 7.74 (s, 1H), 4.06 (s, 3H).

後処理

  1. temperatureAfter the reaction mixture had cooled to room temperature
  2. concentrationit was concentrated in vacuo
  3. additiondiluted with saturated aqueous sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-31ccca9ee4c4403b8381c5710ae5ccca
出典データセット
uspto-grants-2014_09
特許番号
US08822494B2

反応ノート

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