Potassium Carbonate → 6-bromo-4-(1H-pyrazol-4-yl)quinoline

HRID 1625952Notes

Reaction equation

HRID 1625952 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2I.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[N:23][NH:24][CH:25]=2)O1.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]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[C:21]1[CH:22]=[N:23][NH:24][CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 177505956-Bromo-4-iodoquinoline

Product 1

HCID 667816586-bromo-4-(1H-pyrazol-4-yl)quinolineYield 34%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-bromo-4-iodoquinoline (1.37 g, 4 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (852 mg, 4 mmol), dichloro-[1,1′bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (162 mg, 0.2 mmol), 2 M potassium carbonate (6 mL), in dioxane (25 mL) was heated at 100° C. for 1.5 h and cooled to room temperature. The dioxane and water were separated and the dioxane evaporated to get the crude product which was purified on silica gel eluting with ethyl acetate/methanol, 0-3% methanol. A yield of the title compound (340 mg, 34%) was obtained. MS(ES)+ m/e 275 [M+H]+.

Workup

  1. customThe dioxane and water were separated
  2. customthe dioxane evaporated
  3. customto get the crude product which
  4. customwas purified on silica gel eluting with ethyl acetate/methanol, 0-3% methanol

Sources & evidence

ORD record
ord-b186271b9a5a4a64b5c922fefa0ff2f9
Source dataset
uspto-grants-2014_07
Patent number
US08785433B2

Reaction notes

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