Potassium Carbonate → 3-Amino-6-(4-fluorophenyl)picolinamide

HRID 42333Notes

Reaction equation

HRID 42333 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH2:11])=[O:10])=[N:4][C:5](Cl)=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>CN(C=O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[C:3]([C:9]([NH2:11])=[O:10])=[N:4][C:5]([C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 107497043-Amino-6-chloropyridine-2-carboxamide

Product 1

HCID 596479063-Amino-6-(4-fluorophenyl)picolinamideYield 92%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-amino-6-chloro-pyridine-2-carboxylic acid amide (2 g), potassium carbonate (3.2 g), tetrakis(triphenylphosphine) palladium (0.674 g) and 4-fluorophenylboronic acid (1.79 g) in DMF (50 mL) and water (10 mL) was heated to 120° C. for 16 hours. Solvents were removed and 1N HCl (30 ml) was added to the mixture. The resulting solid was filtered to provide 2.48 g of 3-amino-6-(4-fluorophenyl)picolinamide which was characterized by its mass spectrum as follows: MS (m/z) 232 [M+H]+.

Workup

  1. customSolvents were removed
  2. addition1N HCl (30 ml) was added to the mixture
  3. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-b1f82f732dc844c7962596577fe63c41
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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