Phosphorus oxychloride → N-(5-bromo-2-pyridinyl)-(2-nitro)-5fluorophenylcarboxamide

HRID 514731Notes

Reaction equation

HRID 514731 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:7]([C:6]2[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[N+:11]([O-:13])=[O:12])=[O:9])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 706222-Amino-5-bromopyridineHCID 27374205-Fluoro-2-nitrobenzoic acid

Product 1

HCID 22596298N-(5-bromo-2-pyridinyl)-(2-nitro)-5fluorophenylcarboxamideYield 68.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 5-fluoro-2-nitrobenzoic acid (10.0 g, 54 mmol, 1.0 equiv), 2-amino-5-bromopyridine (12.2 g, 1.3 equiv), in 80 mL of pyridine was treated with phosphorous oxychloride (25.3 g, 3.0 equiv) for 30 min. The volatile was evaporated and the residue was redissolved into EtOAc, washed with 1N HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered, and evaporated. The volatile was evaporated, and the product was triturated with diethyl ether to give N-(5-bromo-2-pyridinyl)-(2-nitro)-5-fluorophenylcarboxamide (12.5 g, 68%). MS found for C12H7BrFN3O3 (M+H)+: 340, 342.

Workup

  1. customThe volatile was evaporated
  2. dissolutionthe residue was redissolved into EtOAc
  3. washwashed with 1N HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe volatile was evaporated
  8. customthe product was triturated with diethyl ether

Sources & evidence

ORD record
ord-37ee20ad261542128e56caa3cc46af19
Source dataset
uspto-grants-2015_08
Patent number
US09108922B2

Reaction notes

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