Potassium Phosphate, Tribasic → HCID 90412281, compound

HRID 1521998Notes

Reaction equation

HRID 1521998 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:10]([C:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]=3)=[CH:11][C:3]=12.[F:34][C:35]1[CH:36]=[CH:37][C:38]([O:44][CH3:45])=[C:39](B(O)O)[CH:40]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.O.[Cl-].[Na+].O>[F:8][C:7]1[C:2]([C:37]2[CH:36]=[C:35]([F:34])[CH:40]=[CH:39][C:38]=2[O:44][CH3:45])=[C:3]2[CH:11]=[C:10]([C:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]=3)[N:9]([S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:4]2=[N:5][CH:6]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 90412055HCID 90412055, compound

Product 1

HCID 90412281HCID 90412281, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of Example 231C (2000 mg, 4.07 mmol), (5-fluoro-2-methoxyphenyl)boronic acid (898 mg, 5.28 mmol), potassium phosphate tribasic (2589 mg, 12.20 mmol), and phenylallylchloro[1,3-bis(diisopropylphenyl)-2-imidazol-2-ylidene]palladium(II) (79 mg, 0.122 mmol) in tetrahydrofuran (60 mL) and water (20 mL) was degassed and heated at 60° C. for 3 hours. The mixture was treated with water and brine and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, filtered, concentrated, and purified on silica gel using an ISCO Companion eluting with heptanes/ethyl acetate (7:3 to 6:4) to give the title compound. MS (ESI+) m/z 582.1 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel using an ISCO Companion
  7. washeluting with heptanes/ethyl acetate (7:3 to 6:4)

Sources & evidence

ORD record
ord-bb1523ac95a84d0b8c97575d4b36680e
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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