Potassium Carbonate → HCID 59683642, compound

HRID 2389611Notes

Reaction equation

HRID 2389611 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10])=[O:2].Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.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>[CH3:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=2)=[CH:4][C:3]=1[CH:1]=[O:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 5813924-Chloro-2-methylpyridineHCID 2759225(3-Formyl-4-methoxyphenyl)boronic acid

Product 1

HCID 59683642HCID 59683642, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

A stirred suspension of 3-formyl-4-methoxybenzeneboronic acid (700 mg, 3.89 mmol), 4-chloro-2-picoline (494 mg, 3.89 mmol), potassium carbonate (1.45 g, 10.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (225 mg, 0.19 mmol) in 1,2-dimethoxyethane (14 mL) and water (5 mL) is degassed at RT with N2 for 15 minutes then warmed for 16 h at 85° C. The reaction mixture is then cooled to RT and 2 M HCl (15 mL) added. The aqueous layer is washed with TBME (15 mL) then basified to pH 10 with aqueous K2CO3 and extracted into EtOAc (3×50 mL); The combined organic phases are dried over Na2SO4 and the solvents removed in vacuo to give the title compound.

Workup

  1. customis degassed at RT with N2 for 15 minutes
  2. temperatureThe reaction mixture is then cooled to RT
  3. addition2 M HCl (15 mL) added
  4. washThe aqueous layer is washed with TBME (15 mL)
  5. extractionextracted into EtOAc (3×50 mL)
  6. dry with materialThe combined organic phases are dried over Na2SO4
  7. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-c4504b3ac67e423280c28042210e4ad3
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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