Hydrochloric Acid → 7-Bromo-2-tert-butyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17267Notes

Reaction equation

HRID 17267 reaction equation
[Br:1][C:2]1[C:3](I)=[C:4]([CH3:17])[C:5]([C:15]#[N:16])=[C:6]2[C:10]=1[O:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[N:7]2.[C:19]1(B2OCCCO2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>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.CN(C)C=O>[Br:1][C:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([CH3:17])[C:5]([C:15]#[N:16])=[C:6]2[C:10]=1[O:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[N:7]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 642685Phenylboronic acid 1,3-propanediol esterHCID 685859347-Bromo-2-tert-butyl-6-iodo-5-methyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685849237-Bromo-2-tert-butyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 44%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (300 mg, 0.26 mmol) was added to an N,N-dimethylformamide (60 ml) suspension of 7-bromo-2-tert-butyl-6-iodo-5-methyl-1,3-benzoxazole-4-carbonitrile (I-8) (545 mg, 1.30 mmol), 2-phenyl-1,3,2-dioxaborinane (205 μl, 1.37 mmol), anhydrous potassium phosphate (552 mg, 2.60 mmol), followed by stirring at 100° C. for 1 hour. After cooling, 1 N hydrochloric acid (100 ml) was added, the product was extracted with ethyl acetate (100 ml×2), the organic layer was washed with saturated brine (50 ml×2), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1→6:1) to obtain the entitled compound (210 mg, 44%) as a colorless solid.

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted with ethyl acetate (100 ml×2)
  3. washthe organic layer was washed with saturated brine (50 ml×2)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1→6:1)

Sources & evidence

ORD record
ord-a1e4fbc1556a430bb6ab385bc8c6e195
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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