Sodium Carbonate → HCID 303820, compound

HRID 730297Notes

Reaction equation

HRID 730297 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[Na+].[Na+].[C:15]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>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.COCCOC>[C:15]([C:19]1[CH:24]=[CH:23][C:22]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 27343204-tert-Butylphenylboronic acid

Product 1

HCID 303820HCID 303820, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To 4-bromopyridine hydrochloride (Aldrich) (8.9 g, 46 mmol) and tetrakis(triphenylphosphine)palladium(0) (Aldrich) (1.6 g, 1.4 mmol) was added 1,2-dimethoxyethane (250 mL) with stirring under nitrogen. After 20 min, a solution of Na2CO3 (9.7 g in 70 mL of water) and 4-tert-butylbenzeneboronic acid (9.8 g, 55 mmol) were added sequentially to the mixture. The reaction was stirred at reflux overnight. The reaction mixture was concentrated in vacuo to approximately ⅓ its original volume, and the mixture was extracted with EtOAc (2×100 mL). The combined EtOAc layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by silica gel chromatography (1:5 EtOAc/hexanes) gave the title compound as a white solid. MS (ESI, pos. ion) m/z: 212 (M+1).

Workup

  1. stirringThe reaction was stirred
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. extractionthe mixture was extracted with EtOAc (2×100 mL)
  5. washThe combined EtOAc layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel chromatography (1:5 EtOAc/hexanes)

Sources & evidence

ORD record
ord-0a836492524d4e568c4ad85a9e4ad2b2
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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