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

HRID 1039640Notes

Reaction equation

HRID 1039640 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-582578daa5ef4a2a8803afc8f6716584
Source dataset
uspto-grants-2013_10
Patent number
US08552199B2

Reaction notes

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