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

HRID 626777ノート

反応式

HRID 626777 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-59349fb57e034ea49f76029206146eba
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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