Toluene → HCID 57941029, compound

HRID 1437475Notes

Reaction equation

HRID 1437475 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](/[CH:10]=[CH:11]/[C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)=[N:7][C:6]=2[CH:22]=1.[C:23]1(OB(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(OCC)(=O)C.O1CCCC1.O1CCCC1>[C:23]1([C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8](/[CH:10]=[CH:11]/[C:12]4[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=4)=[N:7][C:6]=3[CH:22]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 68897067HCID 68897067, compound

Product 1

HCID 57941029HCID 57941029, compoundYield 55%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
90 °C

Procedure

Under an argon stream, a mixture of 5-bromo-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]benzoxazole (Compound of Reference Example 44) (129 mg), phenylboric acid (171 mg), tetrakis(triphenylphosphine)palladium(0) (61 mg), 2 M sodium carbonate (1.05 ml), toluene (3.15 ml) and tetrahydrofuran (1.05 ml) was stirred at 90° C. for 24 hours. The reaction mixture was subjected to distribution into ethyl acetate-tetrahydrofuran (3:1, v/v) and water. The organic layer was washed with water and dried over MgSO4, and the solvent was distilled off under reduced pressure. The residue was subjected silica gel column chromatography and the fraction eluted with ethyl acetate-hexane (1:6, v/v) was concentrated under reduced pressure. The resulting crystals were collected by filtration to obtain 5-phenyl-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]benzoxazole (70 mg, 55%). The compound was recrystallized from ethyl acetate-hexane.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. distillationthe solvent was distilled off under reduced pressure
  4. washthe fraction eluted with ethyl acetate-hexane (1:6, v/v)
  5. concentrationwas concentrated under reduced pressure
  6. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-8b9eaaad76334f6a81ba83b2a607990b
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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