Pyridine → tert-Butyl 5-bromopyridine-2-carboxylate

HRID 225764Notes

Reaction equation

[C:1]1([CH3:11])[CH:6]=CC(S(Cl)(=O)=O)=C[CH:2]=1.[Br:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[N:17][CH:18]=1.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(O)(C)(C)C.C(OCC)C>[C:1]([O:20][C:19]([C:16]1[CH:15]=[CH:14][C:13]([Br:12])=[CH:18][N:17]=1)=[O:21])([CH3:11])([CH3:6])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

para-Toluene sulfonyl chloride (262 mg, 1.38 mmol) was added to a solution of 5-bromo-2-carboxypyridine (118 mg, 0.58 mmol) and pyridine (0.3 mL, 0.39 mmol) in tert-butanol (1 mL) and the mixture was stirred at 40° C. for 10 minutes and room temperature for 2 hours. Saturated sodium hydrogen carbonate solution (4 mL) was then added and the mixture was stirred for 5 minutes. Diethyl ether was next added and the bi-phasic mixture was stirred for a further 10 minutes. The organic layer was then separated, washed with brine, dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with pentane:ethyl acetate, 100:0 to 80:20, afforded the title compound as a colourless solid in 73% yield, 110 mg.

Workup

stirringthe mixture was stirred for 5 minutes
stirringthe bi-phasic mixture was stirred for a further 10 minutes
customThe organic layer was then separated
washwashed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customPurification of the residue by column chromatography on silica gel
washeluting with pentane

Sources & evidence

ORD record: ord-04a5612ea3164abf873a5a39f55e4567
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557121B2

Reaction notes

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