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Dimethylformamide → N-((R)-5-bromoindan-2-yl)-5-[(S)-1-(tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxamide

HRID 1039640
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인쇄 미리보기

반응식

HRID 1039640 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@@H:6]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][N:15]=1)=[O:13])[CH2:5]2.CS(O[CH2:26][C@@H:27]1[CH2:31][CH2:30][CH2:29][O:28]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@@H:6]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:26][C@@H:27]3[CH2:31][CH2:30][CH2:29][O:28]3)=[CH:16][N:15]=1)=[O:13])[CH2:5]2
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 18649743(S)-1-(tetrahydrofuran-2-yl)methyl methanesulfonateHCID 66679915N-((R)-5-Bromoindan-2-yl)-5-hydroxypyridine-2-carboxamide

생성물 1

HCID 66679917N-((R)-5-bromoindan-2-yl)-5-[(S)-1-(tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxamide

시약·촉매·용매 1

HCID 962
Water
용매

반응 조건

온도
60 °C

실험 절차

A mixture of N-((R)-5-bromoindan-2-yl)-5-hydroxypyridine-2-carboxamide (1.50 g), (S)-1-(tetrahydrofuran-2-yl)methyl methanesulfonate (0.81 g), cesium carbonate (1.46 g) and DMF (20 ml) was heated to 60° C. for 4 hours. The cooled reaction mixture was admixed with water and extracted with ethyl acetate. The organic phase was washed three times with water, dried over magnesium sulfate and concentrated. This afforded the product with the molecular weight of 417.31 (C20H21BrN2O3); MS (ESI): 417 (M+H+).

후처리

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed three times with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThis afforded the product with the molecular weight of 417.31 (C20H21BrN2O3)

출처 및 근거

ORD 기록
ord-582578daa5ef4a2a8803afc8f6716584
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08552199B2

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