Sodium Carbonate → 2,2-dimethyl-N-[2-methyl-5-[6-[4-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazin-2-yl]phenyl]propanamide

HRID 539793Notes

Reaction equation

HRID 539793 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH3:24])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=3)=[CH:10][N:4]2[N:3]=1.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][C:28]=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>[CH3:20][C:19]([CH3:22])([CH3:21])[C:18]([NH:17][C:15]1[CH:16]=[C:11]([C:9]2[N:8]=[C:5]3[N:4]([CH:10]=2)[N:3]=[C:2]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][C:27]=2[C:26]([F:37])([F:36])[F:25])[CH:7]=[CH:6]3)[CH:12]=[CH:13][C:14]=1[CH3:24])=[O:23]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 44717662(4-(Trifluoromethyl)pyridin-3-yl)boronic acidHCID 86667859HCID 86667859, compound

Product 1

HCID 679828582,2-dimethyl-N-[2-methyl-5-[6-[4-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazin-2-yl]phenyl]propanamideYield 25%

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-chloroimidazo[2,1-f]pyridazin-2-yl)-2-methyl-phenyl]-2,2-dimethyl-propanamide (0.034 g, 0.1 mmol), [4-(trifluoromethyl)-3-pyridyl]boronic acid (0.038 g), bis(triphenylphosphine)palladium(II) dichloride (7 mg), Na2CO3 (0.032 g), and isopropanol-water (1 mL, 3:1). The mixture is heated at 80° C. for 16 hr, cooled, concentrated, taken up in 1:1 EtOAc and CH2Cl2, filtered, concentrated onto celite and purified by silica gel chromatography (10-100% EtOAc in Hexanes) to give the title compound (0.011 g, 25% yield). LCMS m/z=454.5 [M+H]+, tR=2.47 min. (compound same as Example 364)

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. filtrationfiltered
  4. concentrationconcentrated onto celite
  5. custompurified by silica gel chromatography (10-100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-3dffd1fd5ca044dda95e7091208422fb
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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