Potassium Acetate → HCID 178452619, compound

HRID 79744Notes

Reaction equation

HRID 79744 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1([C:12]2[NH:13][C:14](C3C=CC(Br)=CC=3)=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[B:25]1(B2OC(C)(C)C(C)(C)O2)[O:29]C(C)(C)C(C)(C)[O:26]1.CC([O-])=O.[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[BH:25]([OH:29])[OH:26].[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1([C:12]2[NH:13][CH:14]=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 59610360HCID 59610360, compound

Product 1

HCID 178452619HCID 178452619, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

{1-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-cyclobutyl}-carbamic acid tert-butyl ester (110 mg, 0.28) in 1,4-dioxane (2.5 mL) was treated with bis(pinacolato)diboron (150 mg, 0.59 mmol), Pd(PPh3)4 (13 mg, 0.011 mmol), and KOAc (71 mg, 0.73 mmol). The mixture was stirred in a sealed tube at 80° C. for 18 hours. The mixture was filtered through a fritted glass funnel and concentrated. The mixture was subjected to a reverse phase HPLC column (5-95% MeCN—H2O; 0.1% TFA modifier) to afford {1-[1H-imidazol-2-yl]-cyclobutyl}-carbamic acid tert-butyl ester boronic acid.

Workup

  1. filtrationThe mixture was filtered through a fritted glass funnel
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4b999195643a457fb3efd7ca34ace5f5
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

Loading…