Sodium Carbonate → Methyl 4-o-tolyl-nicotinoate

HRID 379366Notes

Reaction equation

HRID 379366 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:18]1([CH3:27])[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O>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(COC)OC>[C:18]1([CH3:27])[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 12574055Methyl 4-chloronicotinate

Product 1

HCID 15887405Methyl 4-o-tolyl-nicotinoateYield 97%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.2 g (6.9 mmol) methyl 4-chloronicotinoate, 20 ml dimethoxyethane, 6.4 ml 2 N sodium carbonate solution, 0.4 g (0.34 mmol) tetrakis(triphenylphosphine)palladium(0) and 1.4 g (10.3 mmol) o-tolylboronic acid was heated under argon at 80° C. for 18 h. After cooling to room temperature, the aqueous phase was separated and washed twice with ethyl. acetate. The combined organic layers were washed with 50 ml brine, dried (sodium sulfate), evaporated and dried in vacuo. The crude oil was subjected to column chromatography to yield 1.5 g (97%) of the title compound as an oil that crystallized upon storage at 0° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe aqueous phase was separated
  3. washwashed twice with ethyl
  4. washThe combined organic layers were washed with 50 ml brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-b1ce9a4ac78b4d1dbf7f80aeeececf2a
Source dataset
uspto-grants-2001_10
Patent number
US06297375B1

Reaction notes

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