Potassium Phosphate, Tribasic → HCID 67960023, compound

HRID 1529257Notes

Reaction equation

HRID 1529257 reaction equation
[CH3:1][O:2][C:3]1[C:12](B(O)O)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl.Cl.Br[C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][N:31]=[C:30]2[C:36]1[N:41]=[C:40]([N:42]2[CH2:47][CH2:46][CH:45]([NH2:48])[CH2:44][CH2:43]2)[CH:39]=[N:38][CH:37]=1>>[CH3:1][O:2][C:3]1[C:12]([C:27]2[CH:28]=[C:29]3[C:33](=[CH:34][CH:35]=2)[NH:32][N:31]=[C:30]3[C:36]2[N:41]=[C:40]([N:42]3[CH2:43][CH2:44][CH:45]([NH2:48])[CH2:46][CH2:47]3)[CH:39]=[N:38][CH:37]=2)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

4

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 16106577(2-Methoxyquinolin-3-yl)boronic acidHCID 67959848HCID 67959848, compound

Product 1

HCID 67960023HCID 67960023, compound

Conditions

Temperature
150 °C

Procedure

To a 5 mL conical vial was added 2-methoxyquinolin-3-ylboronic acid (Frontier Scientific, 89 mg, 0.437 mmol), potassium phosphate (Aldrich, 285 mg, 1.345 mmol), PdCl2(AmPhos) (23.80 mg, 0.034 mmol), and 1-(6-(5-bromo-1H-indazol-3-yl)pyrazin-2-yl)piperidin-4-amine dihydrochloride salt (Example 1) (150 mg, 0.336 mmol) which was sealed, evacuated and back-filled with N2 3×. Dioxane (2.8 mL) and water (0.6 mL) were added, and the reaction mixture was heated at 150° C. for 30 min with microwave irradiation. After the reaction mixtures were filtered, the crude reaction mixture was concentrated and purified on silica gel (eluent: 0 to 4% MeOH (with 2M NH3) in DCM) to afford the title compound. MS (ESI, pos. ion) m/z: 438 (M+1).

Workup

  1. customwas sealed
  2. customevacuated
  3. additionback-filled with N2 3×
  4. additionDioxane (2.8 mL) and water (0.6 mL) were added
  5. customAfter the reaction mixtures
  6. filtrationwere filtered
  7. customthe crude reaction mixture
  8. concentrationwas concentrated
  9. custompurified on silica gel (eluent: 0 to 4% MeOH (with 2M NH3) in DCM)

Sources & evidence

ORD record
ord-be4f381a580d4850a80dbd487fb50ed4
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

Loading…