Triethylamine → N-(4-bromo-3-fluorophenyl)pyridine-2-carboxamide

HRID 2080658

Reaction equation

HRID 2080658 reaction equation
C(N(CC)CC)C.Cl.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](Cl)=[O:16].[Br:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][C:20]=1[F:26]>C(Cl)(Cl)Cl>[Br:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=2)=[O:16])=[CH:21][C:20]=1[F:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 8218484-Bromo-3-fluoroaniline

Product 1

HCID 23145244N-(4-bromo-3-fluorophenyl)pyridine-2-carboxamideYield 92.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2.9 ml of triethylamine and 1.87 g of picolinic acid chloride hydrochloride were added to a chloroform (30 ml) solution of 1 g of 4-bromo-3-fluoroaniline, and stirred at room temperature for 4 hours. The reaction liquid was diluted with chloroform, washed with aqueous saturated sodium bicarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1) to obtain 1.44 g of the entitled compound as a pale yellow crystal.

Workup

  1. customThe reaction liquid
  2. washwashed with aqueous saturated sodium bicarbonate solution and saturated saline water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe solvent was evaporated away
  5. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-d0c1e3ecd2c34458b553a72b4096c6c1
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Linked notes

Loading…