Toluene → HCID 135987528, compound

HRID 2079875Notes

Reaction equation

HRID 2079875 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12](Br)=[CH:11][C:10]=1[C:24]1[N:28]([CH2:29][CH2:30][CH2:31][O:32][CH3:33])[N:27]=[N:26][N:25]=1)C1C=CC=CC=1.[F:34][C:35]([F:47])([F:46])[O:36][C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1.C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>C(O)C>[CH3:33][O:32][CH2:31][CH2:30][CH2:29][N:28]1[C:24]([C:10]2[CH:11]=[C:12]([C:40]3[CH:39]=[CH:38][C:37]([O:36][C:35]([F:34])([F:46])[F:47])=[CH:42][CH:41]=3)[C:13]([OH:15])=[CH:14][C:9]=2[OH:8])=[N:25][N:26]=[N:27]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 57695508HCID 57695508, compound

Product 1

HCID 135987528HCID 135987528, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To the mixture of 5-(2,4-bis-benzyloxy-5-bromo-phenyl)-1-(3-methoxy-propyl)-1H-tetrazole (200 μmol), and 4-(trifluoromethoxy)phenyl boronic acid (2 eq.) was added palladium tetrakistriphenylphosphine (45 mg), followed by toluene (1.2 ml), ethanol (1.2 ml) and saturated NaHCO3 solution (1.2 ml). The resulting mixture was stirred at 80° C. for 12 hours. The product was extracted with ethyl acetate (3×2000 μL), and the combined organic layers were washed with aqueous NaCl (2 ml), and dried. To the residue was added palladium on alumina (100 μL), followed by MeOH (2 ml). Triethyl silane (0.5 ml) was added to the reaction, and the resulting mixture was stirred at room temperature for 70 hours. Hexane (2 ml) was added to the reaction mixture and the top 4.5 ml of the solution was filtered through Baker filter cartridges and then dried in a genevac. The residue was purified by reverse phase HPLC to provide 5-[1-(3-methoxy-propyl)-1H-tetrazol-5-yl]-4′-trifluoromethoxy-biphenyl-2,4-diol. LCMS: 411 [M+H].

Workup

  1. extractionThe product was extracted with ethyl acetate (3×2000 μL)
  2. washthe combined organic layers were washed with aqueous NaCl (2 ml)
  3. customdried
  4. additionTo the residue was added palladium on alumina (100 μL)
  5. additionTriethyl silane (0.5 ml) was added to the reaction
  6. stirringthe resulting mixture was stirred at room temperature for 70 hours
  7. additionHexane (2 ml) was added to the reaction mixture
  8. filtrationthe top 4.5 ml of the solution was filtered through Baker
  9. filtrationfilter cartridges
  10. customdried in a genevac
  11. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-8a4bc4c14c3143988524ff293810f65a
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

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