4-Tert-Butylaniline → n-(4-Tert-butylphenyl)-2-fluoronicotinamide

HRID 2251854Notes

Reaction equation

HRID 2251854 reaction equation
[F:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[C:11]([C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([NH:19][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][CH:9]=[N:10][C:2]=2[F:1])=[CH:20][CH:21]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 698614-Tert-ButylanilineHCID 516892Sodium BicarbonateHCID 219595822-Fluoropyridine-3-carbonyl chloride

Product 1

HCID 21959540n-(4-Tert-butylphenyl)-2-fluoronicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-fluoro-nicotinoyl chloride (5.10 g, 32.0 mmol), 4-tert-butylaniline (5.20 mL, 32.0 mmol), and NaHCO3 (5.40 g, 64.0 mmol) in 50 mL of CH2Cl2 was stirred at RT for 2 h and filtered through Celite®. The solvents were removed and the titled compound was obtained as a white solid after flash column chromatography. MS (ES+): 273.4 (M+H)+. Calc'd for C16H17FN2O-272.32

Workup

  1. filtrationfiltered through Celite®
  2. customThe solvents were removed

Sources & evidence

ORD record
ord-6dabfdf4bba046b0ba30997c1e44766c
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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