Sodium Carbonate → N-[5-[6-(2-fluorophenyl)imidazo[1,2-a]pyridin-2-yl]-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide

HRID 539761Notes

Reaction equation

HRID 539761 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:24]([F:27])([F:26])[F:25])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=3)[N:10]=2)[CH:7]=1.[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(C)C.O>[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:24]([F:26])([F:27])[F:25])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:20])[CH3:21])[CH:16]=3)[N:10]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 67985680N-[5-(6-bromoimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide

Product 1

HCID 67983503N-[5-[6-(2-fluorophenyl)imidazo[1,2-a]pyridin-2-yl]-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamideYield 55%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 21889133Propan-2-ol--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

An 8 mL vial is charged with N-[5-(6-bromoimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide (0.044 g, 0.11 mol), (2-fluorophenyl)boronic acid (Combi-Blocks, 28 mg, 0.2 mmol), Na2CO3 (0.032 g, 0.3 mmol), bis(triphenylphosphine)palladium(II) dichloride (7 mg, 0.01 mmol) and isopropanol-water (1 mL, 3:1). The reaction mixture is stirred at 80° C. for 16 hr, then cooled, concentrated, taken into EtOAc and CH2Cl2 (1:1), filtered, concentrated onto celite and purified by silica gel chromatography (0-100% EtOAc in Hexanes) to give the title compound (25.4 mg, 55% yield). LCMS m/z=456.5 [M+H]+, tR=2.69 min. (compound same as Example 83)

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. filtrationfiltered
  4. concentrationconcentrated onto celite
  5. custompurified by silica gel chromatography (0-100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-3b3067a7ff6e45baa4c0ee24056a2d35
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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