Imidazole → Biphenyl

HRID 2035356Notes

Reaction equation

HRID 2035356 reaction equation
N1[CH:5]=[CH:4]N=C1.B([O-])[O-].[C:9](O)([C:11](F)(F)F)=O>CO>[C:11]1([C:5]2[CH:4]=[CH:11][CH:9]=[CH:11][CH:9]=2)[CH:9]=[CH:4][CH:5]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 795Imidazole2×HCID 6422Trifluoroacetic acid2×HCID 178514824HCID 178514824, compound

Product 1

HCID 7095Biphenyl

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Example 1-4-d was prepared from 1-4-c and 1b in similar fashion to the preparation of 1d from 1b and 1c. 1H NMR (500 MHz, DMSO-d6) δ ppm 0.99-1.60 (m, 18 H) 1.75-2.11 (m, J=73.24 Hz, 6 H) 2.12-2.32 (m, 2 H) 3.32-3.41 (m, 2 H) 3.56 (s, 2 H) 4.63-5.02 (m, 2 H) 6.98-8.28 (m, 10 H) 11.67-12.33 (m, 2H); LC conditions: Phenomenex Luna 3.0×5.0 mm S10, Solvent A—0.1% TFA in 10% MeOH/90% H2O, Solvent B—0.1% TFA in 90% MeOH/10% H2O, 0 to 100% B over 2 min, Stop time=3 min, Flow rate=4 ml/min, Wavelength=220 nm, LC/MS (M+H)+=625.32. Retention time=1.438 min Additional Biphenyl Analogs were Prepared Similarly.

Workup

  1. customtime=3 min, Flow rate=4 ml/min, Wavelength=220 nm, LC/MS (M+H)+=625.32

Sources & evidence

ORD record
ord-bb613b9c988d4d0eba2f0784a9b00298
Source dataset
uspto-grants-2013_11
Patent number
US08574563B2

Reaction notes

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