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

HRID 69317노트

반응식

HRID 69317 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
75 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-31ccca9ee4c4403b8381c5710ae5ccca
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822494B2

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