Hydrogen Bromide → Ethyl 6-(5'-chloro-2'-hydroxy-2-biphenylyl)-2-pyridinecarboxylate

HRID 269570Notes

Reaction equation

HRID 269570 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25]CC2C=CC=CC=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[N:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:17]=[CH:16][CH:15]=2)[CH:7]=1.Br>C(O)(=O)C.C(OCC)C.O.C(=O)([O-])[O-].[K+].[K+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[N:19]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:17]=[CH:16][CH:15]=2)[CH:7]=1

Participants

6

Reactant 2

HCID 260Hydrogen BromideHCID 58730986Ethyl 6-{5'-chloro-2'-[(phenylmethyl)oxy]-2-biphenylyl}2-pyridinecarboxylate

Product 1

HCID 136335797Ethyl 6-(5'-chloro-2'-hydroxy-2-biphenylyl)-2-pyridinecarboxylateYield 82.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 11430Potassium CarbonateSolventHCID 21584184Diethylether waterSolvent

Procedure

Ethyl 6-{5′-chloro-2′-[(phenylmethyl)oxy]-2-biphenylyl}-2-pyridinecarboxylate (1.22 g, 2.75 mmol) was dissolved in acetic acid (5 ml) and 48% hydrogen bromide in acetic acid (5 ml), left at room temperature for 0.5 hours then diluted with diethyl ether/water and basified with potassium carbonate. The organic phase was separated, dried (magnesium sulphate), evaporated and chromatographed on silica eluting with ethyl acetate/iso-hexane (1:3). The product was dissolved in ethanol (20 ml), 60% sodium hydride (2 mg) added and the solution left at room temperature for 16 hours. The resulting solution was acidified with acetic acid, diluted with water/ether and the organic phase washed with saturated sodium bicarbonate solution, dried (magnesium sulphate), evaporated and chromatographed on silica to give 801 mg of colourless gum. LC/MS t=3.33, [MH+] 354.3, 356.3

Workup

  1. customThe organic phase was separated
  2. dry with materialdried (magnesium sulphate)
  3. customevaporated
  4. customchromatographed on silica eluting with ethyl acetate/iso-hexane (1:3)
  5. dissolutionThe product was dissolved in ethanol (20 ml)
  6. addition60% sodium hydride (2 mg) added
  7. additiondiluted with water/ether
  8. washthe organic phase washed with saturated sodium bicarbonate solution
  9. dry with materialdried (magnesium sulphate)
  10. customevaporated
  11. customchromatographed on silica

Sources & evidence

ORD record
ord-1e4a5cd055694557863d99c843dba142
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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