Potassium Carbonate → HCID 69691988, compound

HRID 967820Notes

Reaction equation

HRID 967820 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:19]=[C:18]2I)=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>C(COC)OC.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:19]=[C:18]2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 69743963HCID 69743963, compound

Product 1

HCID 69691988HCID 69691988, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]-2-iodo-4-phenyl-1H-imidazole (594 mg, 1.2 mmol), phenylboronic acid (287 mg, 2.4 mmol), 2M aqueous K2CO3 (3 mL) and bis(triphenylphosphine) palladium(II) chloride (165 mg, 0.24 mmol) in dimethoxyethane (10 mL) was heated at 90° C. for 16 h. After cooling, insoluble materials were removed by Celite pad and the filtrate was washed with 2N NaOH and brine, dried over (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 30:1 to 10:1) to afford 390 mg (73%) of the title compound as pale yellow amorphous: 1H-NMR (CDCl3)δ0.00 (6H, s), 0.89 (9H, s), 2.87 (2H, t, J=6.6 Hz), 3.86 (2H, t, J=6.6 Hz), 7.18-7.33 (7H, m), 7.39-7.52 (5H, m), 7.82 (1H, s), 7.89-7.93 (2H, m).

Workup

  1. temperatureAfter cooling
  2. custominsoluble materials were removed by Celite pad
  3. washthe filtrate was washed with 2N NaOH and brine
  4. dry with materialdried over (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 30:1 to 10:1)

Sources & evidence

ORD record
ord-73834d5f22ab46b1a95ed8b1cd2171b2
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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