Potassium Phosphate, Tribasic → 3-Pyridinol, 6-(phenylmethyl)-

HRID 2075237Notes

Reaction equation

HRID 2075237 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].CO[C:11]1[CH:12]=[CH:13][CH:14]=[C:15](OC)[C:16]=1[C:17]1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.Br[C:39]1[N:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1.B1(CC2C=CC=CC=2)C2CCCC1CCC2>C1COCC1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:17]([C:39]1[N:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1)[C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27628652-Bromo-5-hydroxypyridineHCID 41509249-Benzyl-9-borabicyclo(3.3.1)nonaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 139788063-Pyridinol, 6-(phenylmethyl)-

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

In a sealed tube, a mixture of K3PO4 (16 g, 78 mmol), S-Phos (0.64 g, 1.6 mmol), and palladium acetate (0.29 g, 1.3 mmol) in THF (70 mL) was treated with 6-bromopyridin-3-ol (4.50 g, 26 mmol) and β-benzyl-9-BBN (0.5M solution in THF, 103 mL, 52 mmol). The mixture was heated to 80° C. for 18 h and diluted with EtOAc. The organic phase was washed with 2M aqueous NaOH, brine, dried over MgSO4, and concentrated. Purification by flash chromatography using EtOAc/hexanes gave 6-benzylpyridin-3-ol. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.66 (br. s, 1H), 8.03 (t, J=1.8 Hz, 1H), 7.13-7.30 (m, 4H), 7.07 (d, J=1.9 Hz, 2H), 3.95 (s, 2H). MS (ESI) m/z: Calculated; 185.1 Observed: 186.1 (M++1).

Workup

  1. washThe organic phase was washed with 2M aqueous NaOH, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification by flash chromatography

Sources & evidence

ORD record
ord-15385d9c9d8c49b5b80fa0c114d1b4d9
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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