Cesium carbonate → Ethyl 8-[(3,5-difluoropyridine-4-yl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

HRID 1844192ノート

反応式

HRID 1844192 の反応式
[OH:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl[CH2:19][C:20]1[C:25]([F:26])=[CH:24][N:23]=[CH:22][C:21]=1[F:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:27][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([F:26])[C:20]=1[CH2:19][O:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 86717883Ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylateHCID 867182084-(Chloromethyl)-3,5-difluoropyridine

生成物 1

HCID 86718219Ethyl 8-[(3,5-difluoropyridine-4-yl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

5.0 g (21.34 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate from Example 87A and 3.83 g (23.48 mmol) of 4-(chloromethyl)-3,5-difluoropyridine from Example 115A were initially charged in 306 ml of abs. DMF, and 20.8 g (64.03 mmol) of caesium carbonate were added. The reaction mixture was stirred at 60° C. overnight. The reaction mixture, cooled to RT, was filtered, washed with ethyl acetate and concentrated. The residue was purified by silica gel chromatography (cyclohexane/ethyl acetate gradient=4:1 to 2:1). This gave 5.40 g (70% of theory) of the target compound.

後処理

  1. temperatureThe reaction mixture, cooled to RT
  2. filtrationwas filtered
  3. washwashed with ethyl acetate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (cyclohexane/ethyl acetate gradient=4:1 to 2:1)

出典と根拠

ORDレコード
ord-10789e9e581a42f49dda858e6a82620f
出典データセット
uspto-grants-2015_02
特許番号
US08946215B2

反応ノート

読み込み中…