4-Chloropyridine-2-carboxamide → 4-((6-Aminopyridin-3-yl)oxy)picolinamide

HRID 872971Notes

Reaction equation

HRID 872971 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH2:24])=[O:23])[CH:17]=1>CN(C=O)C.CCOC(C)=O.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH2:24])=[O:23])[CH:17]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 3035434-Chloropyridine-2-carboxamideHCID 42319722-Amino-5-hydroxypyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 900310284-((6-Aminopyridin-3-yl)oxy)picolinamideYield 50%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 6-aminopyridin-3-ol (220 mg, 2 mmol) and t-BuOK (225 mg, 2.16 mmol) in DMF (2.5 mL) was added 4-chloropicolinamide (315 mg, 2 mmol). The reaction was heated to 80° C. for 5 hours, then cooled to rt and diluted with EtOAc (50 mL) and H2O (50 mL). The organic phase was concentrated in vacuo and the residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=30/1) to give the title compound as a brown solid (230 mg, 50%).

Workup

  1. temperaturecooled to rt
  2. concentrationThe organic phase was concentrated in vacuo
  3. customthe residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=30/1)

Sources & evidence

ORD record
ord-850738ae0aa4444ab6fc9710478e7fbd
Source dataset
uspto-grants-2015_03
Patent number
US08975282B2

Reaction notes

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