Potassium Carbonate → 6-(3-Chlorophenyl)-5-methoxy-pyridine-2-carboxylic acid

HRID 927483Notes

Reaction equation

HRID 927483 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[Cl:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:13][C:14]1[CH:19]=[C:18]([C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=2[O:11][CH3:12])[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 2734323(3-Chlorophenyl)boronic acidHCID 74719656-Bromo-5-methoxypyridine-2-carboxylic acid

Product 1

HCID 710872506-(3-Chlorophenyl)-5-methoxy-pyridine-2-carboxylic acidYield 37.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-bromo-5-methoxy-pyridine-2-carboxylic acid (0.3 g, 1 mmol), 3-chlorophenylboronic acid (CAN 63503-60-6, 0.23 g, 1 mmol), tris(dibenzylidene-acetone)-dipalladium(0) (CAN 52409-22-0, 0.12 g), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (CAN 161265-03-8, 0.15 g) and potassium carbonate (0.21 g, 2 mmol) in 1,4-dioxane (10 mL) was stirred for 12 h at 110° C. under a nitrogen atmosphere. The reaction mixture was filtered, concentrated under reduced pressure and purified by column chromatography (silica gel, 10 g, eluting with 10% methanol in methylene chloride) to give the title compound (0.1 g, 29%); MS (EI): m/e=264.0 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. custompurified by column chromatography (silica gel, 10 g, eluting with 10% methanol in methylene chloride)

Sources & evidence

ORD record
ord-82e5c69128dd4a36b21af4ae65d749dd
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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