Methanol → 2-Acetyl-6-phenylpyridine

HRID 353691Notes

Reaction equation

HRID 353691 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6](Br)[N:5]=1)(=[O:3])[CH3:2].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+].CO>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.CCOCC>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 112985782-Acetyl-6-bromopyridine

Product 1

HCID 154979432-Acetyl-6-phenylpyridineYield 89.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a Schlenk tube charged with a solution of 200 mg (1.0 mmol) of 2-acetyl-6-bromopyridine and 23 mg (0.02 mmol) of (Ph3P)4Pd in 10 mL of degassed toluene was added a solution. of 150 mg (1.2 mmol) phenylboronic acid and 270 mg (2.5 mmol) Na2CO3 in 8 mL of degassed 4:1H2O/MeOH. The biphasic mixture was heated to 80° C. with rapid stirring for 1 h. On cooling to RT, Et2O (50 mL) was added and the layers were separated. The organic layer was dried over Na2SO4 and the volatiles were removed by rotary evaporation. The resulting oil was chromatographed on silica with 10-50% CH2Cl2/hexanes eluent to provide 176 mg (89%) of 2-acetyl-6-phenylpyridine as a white powder. 1H NMR (CDCl3); δ 2.84 (s, 3H); 7.43-7.62 (m, 3H); 7.91-8.08 (m, 3 H); 8.18 (d, J=6.6 Hz, 2H). Mass Spec.: m/e 197.

Workup

  1. additionwas added a solution
  2. temperatureOn cooling to RT
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe volatiles were removed by rotary evaporation
  6. customThe resulting oil was chromatographed on silica with 10-50% CH2Cl2/hexanes eluent

Sources & evidence

ORD record
ord-ef4db1fee12f4bef9c426d622412db47
Source dataset
uspto-grants-2004_06
Patent number
US06756195B2

Reaction notes

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