Potassium Phosphate, Tribasic → HCID 58415309, compound

HRID 2075234Notes

Reaction equation

HRID 2075234 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.[Cl:38][C:39]1[C:44]([OH:45])=[CH:43][CH:42]=[C:41](I)[N: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:41]1[N:40]=[C:39]([Cl:38])[C:44]([OH:45])=[CH:43][CH:42]=1)[C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 41509249-Benzyl-9-borabicyclo(3.3.1)nonaneHCID 107774172-Chloro-3-hydroxy-6-iodopyridineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 58415309HCID 58415309, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

A mixture of K3PO4 (12 g, 55 mmol), S-Phos (0.45 g, 1.1 mmol), and palladium acetate (0.21 g, 0.91 mmol) in THF (55 mL) was prepared in a sealed tube. The mixture was treated with 2-chloro-6-iodopyridin-3-ol (4.67 g, 18 mmol) and β-benzyl-9-BBN (0.5M solution in THF, 73 mL, 37 mmol) and heated to 80° C. for 2 h. The crude mixture was diluted with EtOAc, washed with 2M aqueous NaOH, brine, dried over MgSO4, and evaporated. Purification by flash chromatography (EtOAc/hexanes) gave 6-benzyl-2-chloropyridin-3-ol. 1H NMR (300 MHz, CDCl3) δ ppm 7.11-7.41 (m, 6H), 6.94 (d, J=8.2 Hz, 1H), 5.49 (br. s, 1H), 4.06 (s, 2H). MS (ESI) m/z: Calculated; 219.1 Observed: 220.0 (M++1).

Workup

  1. customwas prepared in a sealed tube
  2. washwashed with 2M aqueous NaOH, brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customPurification by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-b2e1fd7776334a09add972526c10caaf
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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