Methanol → Methyl 5-Bromo-4-methylpyridine-3-carboxylate

HRID 468712Notes

Reaction equation

HRID 468712 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:10]=1[CH3:11])[C:7]([OH:9])=[O:8].[CH2:12](Cl)Cl.CO.C[Si](C=[N+]=[N-])(C)C>CCOCC>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:10]=1[CH3:11])[C:7]([O:9][CH3:12])=[O:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 167693Trimethylsilyldiazomethane2×HCID 70606755-Bromo-4-methylnicotinic acid

Product 1

HCID 67974731Methyl 5-Bromo-4-methylpyridine-3-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 5-bromo-4-methylnicotinic acid (223.4 mg, 1.034 mmol) in methylene chloride (3.0 mL, 47 mmol) and methanol (3.0 mL, 74 mmol) was added 2.0 M of trimethylsilyldiazomethane in ether (0.70 mL). The reaction mixture was stirred at room temperature for one hour, and then 2.0 M of trimethylsilyldiazomethane in ether (0.50 mL) was added. After an additional two hours, the crude reaction mixture was evaporated in vacuo to yield 237.2 mg (100%) of methyl 5-bromo-4-methylnicotinate which was carried forward without further purification. LCMS (ESI): M+H=230.2; 1H NMR (400 MHz, DMSO-d6) δ 8.86 (s, 1H), 8.82 (s, 1H), 3.89 (s, 3H), 2.58 (s, 3H).

Workup

  1. waitAfter an additional two hours
  2. customthe crude reaction mixture
  3. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-bd182c0b53c04ba19e54c474afd57981
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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