N-bromobutanimide → 5-broMo-3-(trifluoroMethoxy)pyridin-2-aMine

HRID 2203653Notes

Reaction equation

HRID 2203653 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[C:5]([NH2:10])=[N:6][CH:7]=[CH:8][CH:9]=1.[Br:13]N1C(=O)CCC1=O>ClCCl>[Br:13][C:8]1[CH:9]=[C:4]([O:3][C:2]([F:1])([F:11])[F:12])[C:5]([NH2:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 498711863-(Trifluoromethoxy)pyridin-2-amine

Product 1

HCID 902856745-broMo-3-(trifluoroMethoxy)pyridin-2-aMineYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(trifluoromethoxy)pyridin-2-amine (300 mg, 1.68 mmol) in dichloromethane (8 mL) was added N-bromosuccinimide (450 mg, 2.53 mmol) at 20° C. The reaction mixture was stirred at the same temperature for another 5 min and subsequently concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 15% ethyl acetate in petroleum ether) affording product (220 mg, 51%): 1H NMR (400 MHz, DMSO-d6) δ 8.03 (d, J=2.0 Hz, 1H), 7.75-7.74 (m, 1H), 6.68 (brs, 2H).

Workup

  1. concentrationsubsequently concentrated to dryness in vacuo
  2. customThe resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 15% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-a2785ba5e9cd4888893f89ad5ee35328
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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