N-bromobutanimide → (Rac)-3-[1-(3-bromo-imidazo[1,2-a]pyridin-6-yl)-ethyl]-6-(1-methyl-1h-pyrazol-4-yl)imidazo[1,2-b]pyridazine

HRID 69306ノート

反応式

HRID 69306 の反応式
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH:10]([C:12]3[N:16]4[N:17]=[C:18]([C:21]5[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=5)[CH:19]=[CH:20][C:15]4=[N:14][CH:13]=3)[CH3:11])[CH:7]=[CH:6][C:5]=12.C1C(=O)N([Br:34])C(=O)C1>C(Cl)Cl>[Br:34][C:3]1[N:4]2[CH:9]=[C:8]([CH:10]([C:12]3[N:16]4[N:17]=[C:18]([C:21]5[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=5)[CH:19]=[CH:20][C:15]4=[N:14][CH:13]=3)[CH3:11])[CH:7]=[CH:6][C:5]2=[N:1][CH:2]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 57917425HCID 57917425、化合物

生成物 1

HCID 57917281(Rac)-3-[1-(3-bromo-imidazo[1,2-a]pyridin-6-yl)-ethyl]-6-(1-methyl-1h-pyrazol-4-yl)imidazo[1,2-b]pyridazine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(rac)-3-(1-Imidazo[1,2-a]pyridin-6-yl-ethyl)-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine (Example 293, 607 mg, 1.768 mmol) was dissolved in DCM (18 mL) and NBS (346 mg, 1.944 mmol) was added. It was stirred at rt for 30 min then the solvent was removed. The residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM). Combined fractions were concentrated to give the title compound as a yellow solid (tR 0.7 min (conditions 2), MH+=422, 1H-NMR in DMSO-d6: 8.47 (s, 1H); 8.37 (s, 1H); 8.04 (m, 2H); 7.78 (s, 1H); 7.67 (s, 1H); 7.54 (d, 1H); 7.47 (d, 1H); 7.32 (d, 1H); 4.81 (q, 1H); 3.89 (s, 3H); 1.80 (d, 3H)).

後処理

  1. customthe solvent was removed
  2. customThe residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM)
  3. concentrationCombined fractions were concentrated

出典と根拠

ORDレコード
ord-35572baab7de40f989c3136453622910
出典データセット
uspto-grants-2014_09
特許番号
US08822468B2

反応ノート

読み込み中…