Sodium Carbonate → HCID 69507074, compound

HRID 1623135Notes

Reaction equation

HRID 1623135 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][C:18](=[O:20])[CH3:19])[C:13]([CH2:21][CH2:22][CH3:23])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:24]1([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[N:14]([CH2:15][CH2:16][CH2:17][C:18](=[O:20])[CH3:19])[C:13]([CH2:21][CH2:22][CH3:23])=[N:12][C:7]=4[CH:8]=[N:9][C:10]=3[CH:11]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 69507078HCID 69507078, compound

Product 1

HCID 69507074HCID 69507074, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Conditions

Temperature
100 °C

Procedure

5-(7-Bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one (2.5 g, 6.68 mmol) was dissolved in propanol (25 mL) and water (5 mL) and degassed with nitrogen for 5 minutes. Phenylboronic acid (1.97 g, 7.35 mmol), palladium (II) acetate (7 mg, 0.03 mmol), triphenylphosphine (0.17 g, 0.06 mmol), and sodium carbonate (0.85 g, 8.01 mmol) were added sequentially to the reaction mixture and heated at 100° C. overnight. The mixture was concentrated under reduced pressure and the residue was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated under reduced pressure. Purification was performed with flash column chromatography on silica gel (eluting with 3% methanol in dichloromethane) to obtain 1.0 g of 5-(7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one.

Workup

  1. customwater (5 mL) and degassed with nitrogen for 5 minutes
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with dichloromethane
  4. washwashed with saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification

Sources & evidence

ORD record
ord-8d2fc54254f340e3aaeca65acb76946e
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

Loading…