Potassium Phosphate, Tribasic → HCID 68585492, compound

HRID 17358Notes

Reaction equation

HRID 17358 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:19]1[C:20]([F:32])=[C:21]2[O:25][C:24]([CH3:26])=[N:23][C:22]2=[C:27]([C:30]#[N:31])[C:28]=1[CH3:29]>O1CCOCC1>[F:32][C:20]1[C:19]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:28]([CH3:29])[C:27]([C:30]#[N:31])=[C:22]2[C:21]=1[O:25][C:24]([CH3:26])=[N:23]2

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 685843936-Bromo-7-fluoro-2,5-dimethyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 68585492HCID 68585492, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phenylboronic acid (1.30 g, 10.63 mmol), tetrakistriphenylphosphine palladium(0) (473 mg, 0.41 mmol) and tripotassium phosphate (4.51 g, 21.2 mmol) were added to a 1,4-dioxane (80 ml) solution of 6-bromo-7-fluoro-2,5-dimethyl-1,3-benzoxazole-4-carbonitrile (I-101) (2.2 g, 8.18 mmol), followed by heating under reflux for 3 hours under nitrogen atmosphere. After cooling, the reaction liquid was filtered, the solvent was evaporated away from the filtrate under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and eluted with n-hexane/ethyl acetate (5:1, v/v→4:1, v/v) to obtain a main product. This was washed with isopropyl ether and then collected by filtration to obtain the entitled compound (985 mg, 45%) as a colorless solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours under nitrogen atmosphere
  3. temperatureAfter cooling
  4. customthe reaction liquid
  5. filtrationwas filtered
  6. customthe solvent was evaporated away from the filtrate under reduced pressure
  7. washeluted with n-hexane/ethyl acetate (5:1, v/v→4
  8. custom1, v/v) to obtain a main product
  9. washThis was washed with isopropyl ether
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a19793bbfe5c4bd1b56faf6448f65bec
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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