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

HRID 1844174ノート

反応式

HRID 1844174 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.CS(O[CH2:23][CH:24]1[CH2:27][C:26]([F:29])([F:28])[CH2:25]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:28][C:26]1([F:29])[CH2:27][CH:24]([CH2:23][O:1][C:2]2[C:3]3[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=2)[CH2:25]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 582234121132843-09-4HCID 86717883Ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

生成物 1

HCID 86718191Ethyl 8-[(3,3-difluorocyclobutyl)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

1.85 g (7.89 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate Example 87A and 2.37 g (9.47 mmol) of (3,3-difluorocyclobutyl)methyl methanesulphonate Example 105A were initially charged in 104 ml of DMF, and 10.28 g (31.56 mmol) of caesium carbonate were added. The reaction mixture was stirred at 60° C. overnight. After cooling, the reaction mixture was filtered, the solid was washed thoroughly with ethyl acetate, the filtrate was concentrated and about 150 ml of water were added to the residue. The solid formed was filtered off and dried under high vacuum. This gave 2.51 g (89% of theory; purity 95%) of the title compound.

後処理

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. washthe solid was washed thoroughly with ethyl acetate
  4. concentrationthe filtrate was concentrated
  5. additionabout 150 ml of water were added to the residue
  6. customThe solid formed
  7. filtrationwas filtered off
  8. customdried under high vacuum

出典と根拠

ORDレコード
ord-4fbd1659be474af8b07214e5e99bd258
出典データセット
uspto-grants-2015_02
特許番号
US08946215B2

反応ノート

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