Potassium Carbonate → HCID 59320215, compound

HRID 655282

Reaction equation

HRID 655282 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]1[N:17]3[N:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]3=[N:15][N:14]=1)=[CH:7][CH:6]=2.[CH3:23][N:24]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[N:25]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH3:23][N:24]1[CH:28]=[C:27]([C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][C:8]([CH2:12][C:13]2[N:17]4[N:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]4=[N:15][N:14]=2)=[CH:7][CH:6]=3)[CH:26]=[N:25]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 593202953-Bromo-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline

Product 1

HCID 59320215HCID 59320215, compoundYield 4%

Reagents, catalysts & solvents 3

HCID 53485975CID 53485975CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-bromo-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline (50 mg, 0.141 mmol, 1.0 equiv.) in 1,4-dioxane (1 mL) was degassed with nitrogen and added to a microwave tube containing 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.177 mmol, 1.25 equiv., 37 mg). A degassed solution of potassium carbonate (0.282 mmol, 2 equiv., 39 mg) in water (0.5 mL) was then added to the microwave tube followed by dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (5 mg, 0.0071 mmol, 0.05 equiv). The microwave tube was capped and reacted in a microwave reactor at 100° C. for 30 minutes. The reaction mixture was partitioned between dichloromethane and water, and the organic layer was evaporated and the residue directly adsorbed on silica gel. Purification on silica gel with 0-10% gradient of methanol in dichloromethane, followed by trituration with methanol afforded the title compound (1.8 mg, 0.005 mmol, 4% yield) as a white solid. Analytical data presented in Table 2.

Workup

  1. additionadded to a microwave tube
  2. customThe microwave tube was capped
  3. customreacted in a microwave reactor at 100° C. for 30 minutes
  4. customThe reaction mixture was partitioned between dichloromethane and water
  5. customthe organic layer was evaporated
  6. customPurification on silica gel with 0-10% gradient of methanol in dichloromethane

Sources & evidence

ORD record
ord-e78c386123dd46f984c1be40fe3cec6a
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Linked notes

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