Cesium carbonate → HCID 59320209, compound

HRID 655297Notes

Reaction equation

HRID 655297 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[C:9]([F:12])[C:8]([CH2:13][C:14]1[N:18]3[N:19]=[C:20]([CH2:23][CH3:24])[CH:21]=[CH:22][C:17]3=[N:16][N:15]=1)=[C:7]([F:25])[CH:6]=2.[CH3:26][N:27]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[N:28]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH2:23]([C:20]1[CH:21]=[CH:22][C:17]2[N:18]([C:14]([CH2:13][C:8]3[C:9]([F:12])=[C:10]4[C:5](=[CH:6][C:7]=3[F:25])[N:4]=[CH:3][C:2]([C:30]3[CH:29]=[N:28][N:27]([CH3:26])[CH:31]=3)=[CH:11]4)=[N:15][N:16]=2)[N:19]=1)[CH3:24]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 24966944HCID 24966944, compound

Product 1

HCID 59320209HCID 59320209, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 3-bromo-6-(6-ethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-5,7-difluoro-quinoline (86 mg, 0.2 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.21 mmol, 44 mg) and cesium carbonate (0.6 mmol<195 mg) in 1,4-dioxane (2 mL) at reflux was added [2-[(D-N)methyl]phenyl-c](tricyclohexylphosphine)trifluoroacetato-O-(SP-4-3)-palladium (Bedford, R. B.; Cazin, C. S. J.; Coles, S. J.; Gelbrich, T.; Horton, P. N.; Hursthouse, M. B.; Light, M. E. Organometallics 2003, 22, 987) (0.5 mol %, 0.1 μmol, 0.1 mg). After 30 min the reaction mixture was filtered through a pad of silica gel (2 g) eluting with dichloromethane/methanol (17/3, 12 mL). The filtrate was concentrated onto silica gel and purified via flash column chromatography (SiO2, CH2Cl2:CH3OH 100:0-90:10) to return the title compound as an off white solid (52 mg, 60% yield). Analytical data presented in Table 2.

Workup

  1. temperatureat reflux
  2. filtrationAfter 30 min the reaction mixture was filtered through a pad of silica gel (2 g)
  3. washeluting with dichloromethane/methanol (17/3, 12 mL)
  4. concentrationThe filtrate was concentrated onto silica gel
  5. custompurified via flash column chromatography (SiO2, CH2Cl2:CH3OH 100:0-90:10)

Sources & evidence

ORD record
ord-cc32b2060b3a48718e0a60b4cb9d089d
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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