Sodium Carbonate → 4-(6-methoxypyridin-3-yl)benzoic Acid

HRID 551276Notes

Reaction equation

HRID 551276 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([OH:3])=[O:2].Br[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[N:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:21][O:20][C:17]1[N:18]=[CH:19][C:14]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 27348955-Bromo-2-methoxypyridine

Product 1

HCID 46742594-(6-methoxypyridin-3-yl)benzoic AcidYield 90.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Carboxybenzeneboronic acid (2.87 g, 17.3 mmol), 5-bromo-2-methoxypyridine (3.25 g, 17.3 mmol), 0.4M aqueous sodium carbonate (87 ml, 34.8 mmol) and acetonitrile (86 mL) were combined under nitrogen, and palladium tetrakistriphenylphosphine (1.00 g, 0.87 mmol) added. The reaction mixture was refluxed for 3 hours, cooled to room temperature, and filtered through celite (washed celite with 50:50 acetonitrile/water). Removed acetonitrile in vacuo, diluted residue with water (100 mL) and acidified to pH 2 with 2M HCl. The precipitate which formed was collected, washed with water, and dried under high vacuum to give the product as a white powder (3.6 g, 15.7 mmol). 1H NMR (DMSO) δ 12.90 (br s, 1H), 8.56 (s, 1H), 8.08 (dd, 1H), 7.98 (d, 2H), 7.75 (d, 2H), 6.94 (d, 1H), 3.90 (s, 3H). ESI MS (M+1)+: 230.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. filtrationfiltered through celite (washed celite with 50:50 acetonitrile/water)
  3. customThe precipitate which formed
  4. customwas collected
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-a5b0d0f9e36845d0b363a06d8f43cb8f
Source dataset
uspto-grants-2011_05
Patent number
US07947684B2

Reaction notes

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