Sodium Carbonate → 4-Bromo-2-(2,6-dichlorophenyl)-7-methyl-2H-pyrazolo[4,3-c]pyridine

HRID 626777노트

반응식

HRID 626777 반응식
O(Br)[Br:2].[P+5].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[N:13]1[CH:23]=[C:16]2[CH:17]=[N+:18]([O-])[CH:19]=[C:20]([CH3:21])[C:15]2=[N:14]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[Br:2][C:17]1[C:16]2=[CH:23][N:13]([C:7]3[C:6]([Cl:5])=[CH:11][CH:10]=[CH:9][C:8]=3[Cl:12])[N:14]=[C:15]2[C:20]([CH3:21])=[CH:19][N:18]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 696710992-(2,6-Dichlorophenyl)-7-methyl-2H-pyrazolo[4,3-c]pyridine-5-oxideHCID 178419731HCID 178419731, 화합물

생성물 1

HCID 866970744-Bromo-2-(2,6-dichlorophenyl)-7-methyl-2H-pyrazolo[4,3-c]pyridine수율 38%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
0 °C

실험 절차

Phosphorus(V) oxybromide (921 mg, 3.43 mmol) was slowly added to a suspension of 2-(2,6-dichlorophenyl)-7-methyl-2H-pyrazolo[4,3-c]pyridine-5-oxide (404 mg, 1.37 mmol) in DCE (9.0 mL) at 0° C., under an atmosphere of nitrogen. The reaction mixture was stirred at 0° C. for 30 minutes and then at room temperature overnight. The orange suspension was poured onto saturated aqueous sodium carbonate solution and was stirred for 10 minutes. This was extracted with DCM and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-30% ethyl acetate in cyclohexane) to afford the title compound as a white solid (185 mg, 38% yield). 1H NMR (300 MHz, DMSO-d6): δ 9.20 (s, 1H), 7.90-7.89 (m, 1H), 7.84-7.80 (m, 2H), 7.76-7.72 (m, 1H), 2.45 (d, J=1.2 Hz, 3H).

후처리

  1. customat room temperature
  2. customovernight
  3. stirringwas stirred for 10 minutes
  4. extractionThis was extracted with DCM
  5. washthe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel flash chromatography (0-30% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-59349fb57e034ea49f76029206146eba
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

반응 노트

불러오는 중…