Bromine → 2-(2-Amino-4-pyridyl)-2-bromo-1-(3-methylphenyl)ethanone hydrobromide

HRID 1268728Notes

Reaction equation

HRID 1268728 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)=[O:17])[CH:12]=[CH:11][N:10]=1)=O)(C)(C)C.[Br:25]Br>C(O)(=O)C>[BrH:25].[NH2:8][C:9]1[CH:14]=[C:13]([CH:15]([Br:25])[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)=[O:17])[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 116168302-(2-Tert-butoxycarbonylamino-4-pyridyl)-1-(3-methylphenyl)ethanone

Product 1

HCID 219642042-(2-Amino-4-pyridyl)-2-bromo-1-(3-methylphenyl)ethanone hydrobromideYield 156.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(2-tert-butoxycarbonylamino-4-pyridyl)-1-(3-methylphenyl)ethanone (185 g, 0.566 mol) in acetic acid (400 mL) was added bromine (29.2 mL, 0.566 mol) and the mixture was stirred at 80° C. for 2 hrs. The reaction mixture was concentrated and the residue was crystallized from acetonitrile-ethyl acetate to give the title compound (171 g, yield 78%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was crystallized from acetonitrile-ethyl acetate

Sources & evidence

ORD record
ord-ed9807b8a5304027a0fb62f3bbaebb78
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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