Bromine → 5-(Benzyloxy)-3-bromopyridin-2-amine

HRID 911843Notes

Reaction equation

HRID 911843 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[N:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])(=O)C.[Na+].[Br:22]Br>C(O)(=O)C>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([Br:22])[C:13]([NH2:16])=[N:14][CH:15]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 669951705-Benzyloxy-pyridin-2-ylamine hydrochloride

Product 1

HCID 582090735-(Benzyloxy)-3-bromopyridin-2-amineYield 17%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-(Benzyloxy)pyridin-2-amine hydrochloride (52.3 g, 221 mmol) and sodium acetate (45.3 g, 552 mmol) were dissolved in acetic acid (300 mL). Bromine (11.3 mL, 221 mmol) was added slowly and stirred at ambient temperature for 18 hours. After an aqueous workup, the material was purified over silica gel to give the title compound (10.5 g, 17.0% yield).

Workup

  1. customAfter an aqueous workup, the material was purified over silica gel

Sources & evidence

ORD record
ord-e777de273f744b17bde59e740081637f
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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