Cesium carbonate → HCID 117843166, 화합물

HRID 2209231노트

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HRID 2209231 반응식
[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

참가 물질

7

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

생성물 1

HCID 117843166HCID 117843166, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-75111048523e460b8ea5e7057f6dff62
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376441B2

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