Toluene → HCID 20802836, compound

HRID 1258166Notes

Reaction equation

HRID 1258166 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[N:6][CH:7]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C(O)C>[C:11]1([C:2]2[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[N:6][CH:7]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 8204233-Acetyl-5-bromopyridine

Product 1

HCID 20802836HCID 20802836, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-Bromo-3-acetylpyridine (2 g, 10 mmol), phenylboronic acid (1.5 g, 12 mmol), trans-dibromobis(triphenylphosphine) palladium (II) (0.4 g, 0.5 mmol), toluene (60 ml), ethanol (20 ml) and 2M aqueous sodium carbonate (40 ml) was refluxed for 1 hour under a nitrogen atmosphere. The mixture was diluted with ethyl acetate and the organic phase was washed with water and brine, dried and evaporated. The crude product was chromatographed on silica gel eluting with a gradient of 0-100% EtoAc in hexane to afford the: 5-(Phenyl)-3-acetylpyridine as a solid. 2 g (10 mmol, 100%). TLC Rf 0.3 (1:1 hexane/EtOAc); MS: 198.5 (M+H); 1H NMR (DMSO) δ 9.12 (dd, J=2.2 Hz, 2H), 8.50 (t, J=2.1 Hz, 1H), 7.83 (d, J=8.1 Hz, 2H), 7.54 (t, J=7.7 Hz, 2H), 7.49 (t, J=7.7 Hz, 1H), 3.02 (s, 3H); 13C NMR δ 197.51, 151.30, 148.12, 136.14, 135.51, 134.05, 133.34, 132.00, 129.91, 129.78, 129.19, 127.64, 27.14.

Workup

  1. temperaturewas refluxed for 1 hour under a nitrogen atmosphere
  2. washthe organic phase was washed with water and brine
  3. customdried
  4. customevaporated
  5. customThe crude product was chromatographed on silica gel eluting with a gradient of 0-100% EtoAc in hexane

Sources & evidence

ORD record
ord-8331c8635b9546d79a6ed6ac95d01c02
Source dataset
uspto-grants-2013_06
Patent number
US08466154B2

Reaction notes

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