4-Fluoroaniline → 6-Bromo-N-(4-Fluorophenyl)Nicotinamide

HRID 859164Notes

Reaction equation

HRID 859164 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:16][C:15]2[CH:17]=[CH:18][C:12]([F:11])=[CH:13][CH:14]=2)=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 234995286-Bromonicotinoyl chloride

Product 1

HCID 218782716-Bromo-N-(4-Fluorophenyl)NicotinamideYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 6-bromonicotinoyl chloride (0.5 g, 2.5 mmol) in dry chloroform (10 mL) was added 4-fluoroaniline (0.33 mL, 3.5 mmol) and 2-ethyoxy-1-ethoxycarbonyl-1,2-dihydroquinoline, (0.85 g, 3.5 mmol). The mixture was stirred for 12 h, diluted with hexanes and the solids isolated by filtration. Purification by trituration using ethyl acetate/hexanes gave 0.53 g (73%) of the desired product as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 10.51 (s, 1H), 8.87 (m, 1H), 8.20 (m, 1H), 7.82 (m, 1H), 7.74 (m, 2H), 7.19 (m, 2H).

Workup

  1. customthe solids isolated by filtration
  2. customPurification by trituration

Sources & evidence

ORD record
ord-b63c3a78dba74290b4f7fdc6ed0d07fa
Source dataset
uspto-grants-2006_12
Patent number
US07151112B1

Reaction notes

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