Cesium carbonate → HCID 117843166、化合物

HRID 2209231ノート

反応式

HRID 2209231 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]2[N:6]([N:8]=[CH:9][CH:10]=2)[CH:7]=1.CS(O[C@H:17]([C@@H:19]1[CH2:23][C:22](=[O:24])[N:21]([C@@H:25]([C:27]2[CH:32]=[CH:31][C:30](OC)=[CH:29][CH:28]=2)[CH3:26])[CH2:20]1)[CH3:18])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([O:11][C@@H:17]([C@H:19]2[CH2:20][N:21]([C@@H:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH3:26])[C:22](=[O:24])[CH2:23]2)[CH3:18])[C:5]2[N:6]([N:8]=[CH:9][CH:10]=2)[CH:7]=1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 67207447HCID 67207447、化合物HCID 117842947(S)-1-((R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidin-3-yl)ethyl methanesulfonate

生成物 1

HCID 117843166HCID 117843166、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

To a solution of 6-bromopyrazolo[1,5-a]pyridin-4-ol (125 mg, 0.587 mmol) in DMF (4 mL) was added (S)-1-((R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidin-3-yl)ethyl methanesulfonate 1.30 (220 mg, 0.645 mmol) and Cs2CO3 (239 mg, 0.733 mmol) and the reaction mixture was heated at 90° C. for 2 h. The reaction mixture was diluted with EtOAc and water, the layers were separated and the aqueous layer was extracted with EtOAc. The combined organics were dried, filtered, and concentrated. The residue was purified by flash chromatography to afford (R)-4-((R)-1-(6-bromopyrazolo[1,5-a]pyridin-4-yloxy)ethyl)-1-((R)-1-phenylethyl)pyrrolidin-2-one 6.01.

後処理

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. customThe combined organics were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-75111048523e460b8ea5e7057f6dff62
出典データセット
uspto-grants-2016_06
特許番号
US09376441B2

反応ノート

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