Potassium Carbonate → HCID 86682279, compound

HRID 540454Notes

Reaction equation

HRID 540454 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8](Br)=[CH:7][N:6]=1)=[O:4].[O:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)[CH3:14].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[CH3:14][O:13][C:15]1[CH:20]=[CH:19][C:18]([C:8]2[C:9]([CH3:11])=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[N:6][CH:7]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 56763836Methyl 5-bromo-4-methylpyridine-2-carboxylate

Product 1

HCID 86682279HCID 86682279, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178454861HCID 178454861, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-bromo-4-methylpyridine-2-carboxylic acid methyl ester (2.207 g, 9.59 mmol), 4-methoxylphenylboronic acid (1.604 g, 10.55 mmol) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (0.313 g, 0.480 mmol) in THF (30 mL) was added potassium carbonate (2.0 M in water, 10.1 mL, 20.15 mmol). The mixture was purged with nitrogen and heated at 50° C. for 1 hour and at 60° C. for 5 hours. The reaction was poured into ethyl acetate and was washed with brine, dried over sodium sulfate, filtered and concentrated. It was purified by column chromatography to yield methyl 5-(4-methoxyphenyl)-4-methylpyridine-2-carboxylate (2.47 g, 9.59 mmol) as a pink solid. MS ESI calc'd. for C15H16NO3 [M+H]+ 258.1. found 258.1.

Workup

  1. customThe mixture was purged with nitrogen
  2. additionThe reaction was poured into ethyl acetate
  3. washwas washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customIt was purified by column chromatography

Sources & evidence

ORD record
ord-5c96c6f5b4f24c918a4982cca7e29fe2
Source dataset
uspto-grants-2014_10
Patent number
US08871738B2

Reaction notes

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