Diisopropylethylamine → N'-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)-2,2-difluoroacetohydrazide

HRID 1925136ノート

反応式

HRID 1925136 の反応式
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([F:15])([F:14])[C:9]([O:11]CC)=O)=[CH:4][CH:3]=1.[Br:16][C:17]1[CH:18]=[CH:19][C:20]([NH:23][NH2:24])=[N:21][CH:22]=1.CCN(C(C)C)C(C)C>CO>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([NH:23][NH:24][C:9](=[O:11])[C:8]([C:5]2[N:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([F:14])[F:15])=[N:21][CH:22]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 115356995-Bromo-2-hydrazinopyridineHCID 46941483Ethyl 2-(6-chloropyridazin-3-yl)-2,2-difluoroacetate

生成物 1

HCID 59233291N'-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)-2,2-difluoroacetohydrazide収率 77%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of ethyl 2-(6-chloropyridazin-3-yl)-2,2-difluoroacetate (10.8 g, 45.6 mmol) and 5-bromo-2-hydrazinylpyridine (8.58 g, 45.6 mmol) in anhydrous MeOH (100 mL) was added DIEA (5.90 g, 45.6 mmol). The reaction was stirred at ambient temperature for 18 hrs. The solvent was removed via rotary evaporation and the resulting material was reconstituted in EtOAc. The organic phase was washed with water and concentrated to dryness. The resulting residue was purified by MPLC (EtOAc) to provide the title compound, N′-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)-2,2-difluoroacetohydrazide 45E (13.3 g, 35.1 mmol, 77% yield). 1H NMR (400 MHz, CDCl3) δ ppm 6.62 (d, J=8.84 Hz, 1 H) 7.11 (d, J=9.35 Hz, 1 H) 7.47-7.60 (m, 2 H) 8.06 (d, J=2.53 Hz, 1 H). ESI-MS:m/z 377.9 (M+H)+.

後処理

  1. customThe solvent was removed via rotary evaporation
  2. washThe organic phase was washed with water
  3. concentrationconcentrated to dryness
  4. customThe resulting residue was purified by MPLC (EtOAc)

出典と根拠

ORDレコード
ord-7debc1cd7ee945158af263b135947272
出典データセット
uspto-grants-2012_05
特許番号
US08178534B2

反応ノート

読み込み中…