Sodium Carbonate → HCID 86702537, compound

HRID 877063Notes

Reaction equation

HRID 877063 reaction equation
Br[C:2]1[C:3]2[C:7]([CH:8]=[CH:9][CH:10]=1)=[N:6][N:5]1[CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13]([Cl:15])=[N:14][C:4]=21.[C:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)#[N:23].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>O>[Cl:15][C:13]1[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][N:5]2[N:6]=[C:7]3[C:3]([C:2]([C:27]4[CH:28]=[CH:29][C:24]([C:22]#[N:23])=[CH:25][CH:26]=4)=[CH:10][CH:9]=[CH:8]3)=[C:4]2[N:14]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27343264-Cyanophenylboronic acidHCID 86702538HCID 86702538, compound

Product 1

HCID 86702537HCID 86702537, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
105 °C

Procedure

400 mg (1.12 mmol) 10-Bromo-2-chloro-3-phenylpyrimido[1,2-b]indazole, intermediate example Int-1-3, 172.1 mg (1.17 mmol) 4-cyanophenylboronic acid, 91 mg (0.112 mmol) bis(diphenylphosphino)ferrocenedichloropalladium(II) and 354.6 mg (3.35 mmol) sodium carbonate in 12 mL degassed dioxane and 1.68 mL water were heated in the microwave for 45 min. at 105° C. The reaction mixture was poured on a mixture of water/saturated ammonium chloride/dichloromethane and stirred vigorously for 30′. The organic phase was separated, washed twice with brine and dried (sodium sulfate). After filtration and evaporation of the solvent the residue was purified by HPLC yielding 114 mg of the title compound.

Workup

  1. customThe organic phase was separated
  2. washwashed twice with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationAfter filtration and evaporation of the solvent the residue
  5. customwas purified by HPLC

Sources & evidence

ORD record
ord-ae04f1eebc6c485bae97c23f8c08f166
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

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