Sodium Carbonate → HCID 68089037, compound

HRID 539784Notes

Reaction equation

HRID 539784 reaction equation
Cl[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])=[N:6][N:5]2[CH:17]=1.[CH3:18][C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][C:22](B2OC(C)(C)C(C)(C)O2)=[CH:21][N:20]=1.C([O-])([O-])=O.[Na+].[Na+]>CC(O)C.O>[F:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:7]1[CH:8]=[CH:9][C:4]2[N:5]([CH:17]=[C:2]([C:22]3[CH:21]=[N:20][C:19]([CH3:18])=[C:24]([N+:25]([O-:27])=[O:26])[CH:23]=3)[N:3]=2)[N:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 57516276HCID 57516276, compoundHCID 68089523HCID 68089523, compound

Product 1

HCID 68089037HCID 68089037, compoundYield 11.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-chloro-6-(2-fluorophenyl)imidazo[1,2-b]pyridazine (0.100 g, 0.403 mmol), 2-methyl-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.605 mmol), Na2CO3 (2.01 mmol) in 2-propanol (3.75 mL) and water (1.25 mL) that has been degassed with N2 (5 minutes) is added PdCl2(PPh3)2(0.0403) mmol). The mixture is heated at 80° C. for 12 hours, then cooled, concentrated under reduced pressure, added sat. aqueous NaHCO3 (20 mL) and extracted with EtOAc (3×20 mL). Organic layer is collected, dried over Na2SO4, filtered and concentrated to dryness. The crude product is purified via chromatography (hexanes to EtOAc) to afford the title compound (0.016 g, 11%) as a white solid: Rf 0.38 (1:1 EtOAc:hexanes); LCMS (m/z)=350.3 [M+H]+, tR=2.71 min.

Workup

  1. customhas been degassed with N2 (5 minutes)
  2. additionis added PdCl2(PPh3)2(0.0403) mmol)
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. additionadded sat. aqueous NaHCO3 (20 mL)
  6. extractionextracted with EtOAc (3×20 mL)
  7. customOrganic layer is collected
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. customThe crude product is purified via chromatography (hexanes to EtOAc)

Sources & evidence

ORD record
ord-b4eab60b2f534421b96bf6433958e68c
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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