Potassium Carbonate → 6-(6-Methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-3-vinyl-quinoline

HRID 655304Notes

Reaction equation

HRID 655304 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.[CH:23](B(O)O)=[CH2:24].C([O-])([O-])=O.[K+].[K+].O1CCOCC1>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].O>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]2[N:17]([C:13]([CH2:12][C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[N:4]=[CH:3][C:2]([CH:23]=[CH2:24])=[CH:11]4)=[N:14][N:15]=2)[N:18]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 4683185Vinylboronic acidHCID 593202953-Bromo-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline

Product 1

HCID 249669426-(6-Methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-3-vinyl-quinolineYield 35%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 962WaterSolvent

Procedure

To a microwave vessel was added 3-bromo-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline (500 mg, 1.41 mmol, 1 equiv), vinyl boronic acid (299 uL, 1.76 mmol, 1.25 equiv), K2CO3 (390 mg, 2.82 mmol, 2.0 equiv) followed by 1,4-dioxane (10 mL) and water (5 mL). The solution was degassed with nitrogen for 10 min and then dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (51 mg, 0.07 mmol, 0.05 equiv) was added. The microwave vessel was capped and reacted in a microwave reactor at 130° C. for 30 min. The microwave vessel was cooled and then the mixture was extracted into dichloromethane and washed with water. The volatiles were removed in vacuo and the residue absorbed onto silica gel and purified by flash chromatography (SiO2, CH2Cl2:CH3OH 100:0-80:20) to obtain the title compound as a brown oil (35% yield). Analytical data presented in Table 1.

Workup

  1. customThe solution was degassed with nitrogen for 10 min
  2. customThe microwave vessel was capped
  3. customreacted in a microwave reactor at 130° C. for 30 min
  4. temperatureThe microwave vessel was cooled
  5. extractionthe mixture was extracted into dichloromethane
  6. washwashed with water
  7. customThe volatiles were removed in vacuo
  8. customthe residue absorbed onto silica gel
  9. custompurified by flash chromatography (SiO2, CH2Cl2:CH3OH 100:0-80:20)

Sources & evidence

ORD record
ord-b796d5fdb4244f89a7e5df2305cfdf02
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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