Phosphorus oxychloride → HCID 59233259、化合物

HRID 1925137ノート

反応式

HRID 1925137 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10](=O)[C:11]([C:14]2[N:15]=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=2)([F:13])[F:12])=[N:6][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)Cl.O=P(Cl)(Cl)Cl>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([C:11]([C:14]3[N:15]=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([F:13])[F:12])=[N:9][N:8]=2)[CH:7]=1

参加物

4

反応物 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 59233291N'-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)-2,2-difluoroacetohydrazide

生成物 1

HCID 59233259HCID 59233259、化合物収率 84%

反応条件

温度
140 °C

実験手順

A mixture of N′-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)-2,2-difluoroacetohydrazide (1.0 g, 2.64 mmol) and PCl5 (1.2 g, 8 mmol) in POCl3 (40.5 g, 264 mmol) was heated at 140° C. in a sealed tube for 18 hrs. Solvent was removed via rotary evaporation, and the resulting residue was reconstituted in EtOAc. The organic solution was washed with saturated NaHCO3, dried with MgSO4, filtered, and concentrated to dryness. The resulting material was purified via MPLC (Hex:EtOAc, 50-100% gradient) to provide the title compound, 6-bromo-3-((6-chloropyridazin-3-yl)difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine 45F (0.8 g, 2.21 mmol, 84%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.75 (dd, J=9.85, 1.77 Hz, 1 H) 8.01 (dd, J=9.85, 1.01 Hz, 1 H) 8.31 (d, J=9.09 Hz, 1 H) 8.42-8.51 (m, 1 H) 8.93 (s, 1 H). ESI-MS:m/z 359.9 (M+H)+.

後処理

  1. customSolvent was removed via rotary evaporation
  2. washThe organic solution was washed with saturated NaHCO3
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe resulting material was purified via MPLC (Hex:EtOAc, 50-100% gradient)

出典と根拠

ORDレコード
ord-1b360e952c4746729feba85fba6764cc
出典データセット
uspto-grants-2012_05
特許番号
US08178534B2

反応ノート

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