Cesium carbonate → 4-(4-amino-3-methylphenoxy)-N-methylpyridine-2-carboxamide

HRID 2370553Notes

Reaction equation

HRID 2370553 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([OH:8])=[CH:6][CH:7]=1.Cl[C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]([NH:19][CH3:20])=[O:18])[CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([C:17]([NH:19][CH3:20])=[O:18])[CH:12]=2)=[CH:4][C:3]=1[CH3:9]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 178194-Amino-m-cresolHCID 14768144-Chloro-N-methylpicolinamide

Product 1

HCID 231372464-(4-amino-3-methylphenoxy)-N-methylpyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
75 °C

Procedure

To the solution of 4-amino-m-cresol (125 mg, 1.01 mmol, 1.0 eq) in 1 mL of NMP was added 4-chloro-N-methylpicolinamide (189 mg, 1.11 mmol, 1.1 eq) and cesium carbonate (658 mg, 2.02 mmol, 2.0 eq) at room temperature. The reaction mixture was stirred at 75° C. for 12 hours, thereafter the mixture was diluted with water (ca. 50 mL) and aqueous layer extracted with ethyl acetate (ca. 50 mL×3). Combined organic layers were dried over sodium sulfate, filtered and condensed under reduced pressure to give sufficiently pure crude product which was carried to next step without further purification. LC/MS (m/z) [258.1] (MH+).

Workup

  1. extractionextracted with ethyl acetate (ca. 50 mL×3)
  2. dry with materialCombined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customcondensed under reduced pressure
  5. customto give sufficiently pure crude product which
  6. customwas carried to next step without further purification

Sources & evidence

ORD record
ord-eb7cb584233e44e2b5a015078a4923ea
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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