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Sodium Carbonate → 4-(6-Methylpyridin-2-yl)benzoic acid

HRID 494184
Notes
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Reaction equation

HRID 494184 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:15]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([OH:17])=[O:16]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:4]1[N:3]=[C:2]([C:21]2[CH:22]=[CH:23][C:18]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=2)[CH:7]=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 792052-Bromo-6-methylpyridineHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 534263364-(6-Methylpyridin-2-yl)benzoic acidYield 77%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst
HCID 962WaterSolvent
HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred, degassed mixture of 2-bromo-6-methylpyridine (3 g, 17 mmol), sodium carbonate (10.8 g, 100 mmol) and 4-carboxybenzeneboronic acid (2.3 g, 14 mmol) in DME (150 ml) and water (150 ml) under an argon atmosphere was added tetrakis(triphenylphosphine) palladium (0) (350 mg) and the mixture heated to reflux for 18 h. On cooling, ˜50% of the solvent was removed in vacuo and the residual aqueous solution was washed with EtOAc, then acidified to pH1 with concentrated HCl and washed with further EtOAc. The aqueous was then adjusted to pH 5 by addition of potassium carbonate causing formation of a white precipitate which was collected by filtration, washed with water and dried to give the title compound as a white solid (2.3 g). MS (ES): MH+ 212.

Workup

  1. customTo a stirred, degassed
  2. temperaturethe mixture heated
  3. temperatureto reflux for 18 h
  4. temperatureOn cooling
  5. custom˜50% of the solvent was removed in vacuo
  6. washthe residual aqueous solution was washed with EtOAc
  7. washwashed with further EtOAc
  8. additionThe aqueous was then adjusted to pH 5 by addition of potassium carbonate causing formation of a white precipitate which
  9. filtrationwas collected by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-982d8bf5dc474d4589f10314da6112be
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07538121B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes