Ammonia → Methyl 5-(4-methoxyphenyl)pyridine-3-carboxylate

HRID 477047Notes

Reaction equation

HRID 477047 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[Na+].[Na+].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](OB(O)O)=[CH:22][CH:21]=1.N>C1(C)C=CC=CC=1.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=2)[C:7]([O:9][CH3:10])=[O:8])=[CH:22][CH:21]=1

Participants

9

Reactant 4

HCID 222AmmoniaHCID 10340Sodium Carbonate2×HCID 699336Methyl 5-bromopyridine-3-carboxylateHCID 147699944-Methoxyphenyl boric acid

Product 1

HCID 14769995Methyl 5-(4-methoxyphenyl)pyridine-3-carboxylateYield 24.7%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

2.16 g of methyl 5-bromonicotinate and 350 mg of tetrakis(triphenylphosphine)palladium were dissolved in 20 ml of toluene, and under a nitrogen current, 10 ml of a 2M aqueous solution of sodium carbonate and a suspension of 1.82 g of (4-methoxyphenyl)boric acid in 5 ml of methanol were added. The mixture was stirred at a bath temperature of 80° C. for 12 hours. To the reaction solution were added 100 ml of methylene chloride, 50 ml of a 2M aqueous solution of sodium carbonate and 5 ml of conc. aqueous ammonia to perform extraction. The organic layer was separated, and the solvent was evaporated. The residue was subjected to silica gel column chromatography. The column was eluted with a 3:7 mixture of ethyl acetate and hexane. The solvent was evaporated from the eluate to give 600 mg (yield 24.7%) of methyl 5-(4-methoxyphenyl)nicotinate as colorless needles having a melting point of 99° to 101° C.

Workup

  1. additionwere added
  2. extractionextraction
  3. customThe organic layer was separated
  4. customthe solvent was evaporated
  5. washThe column was eluted with a 3:7 mixture of ethyl acetate and hexane
  6. customThe solvent was evaporated from the eluate

Sources & evidence

ORD record
ord-0bc534388d90435daed9eaaade7b5428
Source dataset
uspto-grants-1989_12
Patent number
US04886822

Reaction notes

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