Sodium Carbonate → 6-Phenylpyridine-2-carbaldehyde

HRID 31735Notes

Reaction equation

HRID 31735 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].Br[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=[O:24])[N:18]=1>C1(C)C=CC=CC=1.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>[CH:23]([C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:18]=1)=[O:24]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 135224166-Phenylpyridine-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Phenylboronic acid (1.46 g, 12 mmol) and Na2CO3 (2.65 g, 25 mmol) were dissolved in 60 mL of degassed 4:1H2O/MeOH. This solution was added via cannula to a solution of 1.86 g (10 mmol) of 2-bromo-6-formylpyridine and 116 mg (0.10 mmol) of Pd(PPh3)4 in 50 mL of degassed toluene. The biphasic mixture was vigorously stirred and heated at 70° C. under N2 for 4 h. On cooling to RT, the organic phase was separated and the aqueous phase was washed with 3×25 mL of Et2O. The combined organic extracts were washed with 3×25 mL of H2O and 20 mL of brine and dried over Na2SO4. After removing the volatiles in vacuo, the resultant brown oil was chromatographed on silica with hexanes/CH2Cl2. Clean fractions were combined and the volatiles were removed to provide 2-formyl-6-phenylpyridine as a white solid.

Workup

  1. customof degassed 4:1H2O/MeOH
  2. temperatureOn cooling to RT
  3. customthe organic phase was separated
  4. washthe aqueous phase was washed with 3×25 mL of Et2O
  5. washThe combined organic extracts were washed with 3×25 mL of H2O and 20 mL of brine
  6. dry with materialdried over Na2SO4
  7. customAfter removing the volatiles in vacuo
  8. customthe resultant brown oil was chromatographed on silica with hexanes/CH2Cl2
  9. customthe volatiles were removed

Sources & evidence

ORD record
ord-6c5c7c74bbe5405589c23f3977ea9c4a
Source dataset
uspto-grants-2008_09
Patent number
US07425661B2

Reaction notes

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