Potassium Carbonate → HCID 57824527, compound

HRID 1925432Notes

Reaction equation

HRID 1925432 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CCOCC.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>[F:16][C:15]([F:18])([F:17])[O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[N:4]=[N:3][C:2]([C:23]3[CH:24]=[CH:25][C:20]([NH2:19])=[CH:21][CH:22]=3)=[CH:7][CH:6]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27346154-Aminophenylboronic acidHCID 43583892HCID 43583892, compound

Product 1

HCID 57824527HCID 57824527, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution containing 3-chloro-6-(4-trifluoromethoxyphenyl)-pyridazine (157 mg, 0.57 mmol), 4-aminophenylboronic acid (118 mg, 0.86 mmol) and 2 M K2CO3 (0.57 mL, 1.14 mmol) dissolved in 3.5 mL of dry 1,4-dioxane was added dichlorobis(triphenylphosphine)palladium(II) (4 mg, 0.006 mmol). The mixture was irradiated using a CEM Discover microwave at 190° C. for 30 min. The mixture was diluted with 100 mL of ether and washed with brine (30 mL). The organic phase was then dried over MgSO4, filtered and concentrated. The residue was purified via radial chromatography using a 97:3 CHCl3/CH3OH solution as the eluent (Rf=0.26) to afford the title compound (105 mg, 56%). 1H NMR (400 MHz, CDCl3) δ 8.18 (d, J=8.6 Hz, 2H), 8.01 (d, J=8.6 Hz, 2H), 7.30-7.45 (m, 4H), 6.82 (d, J=8.6 Hz, 2H), 3.96 (bs, 2H); EIMS 331 (M+).

Workup

  1. customThe mixture was irradiated
  2. customat 190° C.
  3. customfor 30 min
  4. washwashed with brine (30 mL)
  5. dry with materialThe organic phase was then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified via radial chromatography

Sources & evidence

ORD record
ord-3d5dcd0e6d3449f7b706f174747a7f3f
Source dataset
uspto-grants-2012_05
Patent number
US08178658B2

Reaction notes

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