Potassium Phosphate, Tribasic → HCID 25159029, compound

HRID 1894642Notes

Reaction equation

HRID 1894642 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:16]=[CH:17][N:18]([CH2:20][CH3:21])[CH3:19])[C:5]([CH3:15])=[N:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13].[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[CH:3]=[C:4]([N:16]=[CH:17][N:18]([CH2:20][CH3:21])[CH3:19])[C:5]([CH3:15])=[N:6][C:7]=2[O:8][CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acidHCID 25159028HCID 25159028, compound

Product 1

HCID 25159029HCID 25159029, compoundYield 126.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

In a 10 ml single-necked round-bottomed flask equipped with a condensor (equipment flame-dried), 160 mg of crude N′-[5-bromo-2-methyl-6-(4-methyl-pentyloxy)-pyridin-3-yl]-N-ethyl-N-methyl-formamidine and 77.2 mg p-chlorophenyl boronic acid are dissolved in 1.20 ml of dioxane. To this solution, 162 mg of K3PO4 in 0.60 ml of water is added at ambient temperature under Argon atmosphere. The resulting biphasic mixture is degassed under Argon atmosphere for 20 minutes, whereupon 3.0 mg of tricyclohexylphosphine and 2.6 mg of bis(benzylideneacetone)palladium are added. The resulting suspension is vigorously stirred at a temperature of 100° C. for 5 hours. After letting the reaction mixture reach ambient temperature, 5.0 ml of a saturated aqueous NH4Cl solution is added. The water phase is extracted with AcOEt. The organic phase is dried over sodium sulfate, filtered and the solvent removed in vacuo to get 220 mg of a yellow oil. Purification by flash chromatography over a silica gel cartridge (20 g; 60 ml) of a solid deposition with heptane/ethyl acetate 9:1, then 4:1, then 3:2 (v:v) gave 80 mg of the compound as a yellow oil.

Workup

  1. customThe resulting biphasic mixture is degassed under Argon atmosphere for 20 minutes, whereupon 3.0 mg of tricyclohexylphosphine and 2.6 mg of bis(benzylideneacetone)palladium
  2. additionare added
  3. customreach ambient temperature
  4. addition5.0 ml of a saturated aqueous NH4Cl solution is added
  5. extractionThe water phase is extracted with AcOEt
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-eb9852c98f1c4c13beccddbd4ab52725
Source dataset
uspto-grants-2013_08
Patent number
US08513286B2

Reaction notes

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