Toluene → HCID 59515813, compound

HRID 418473Notes

Reaction equation

HRID 418473 reaction equation
Br[C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH:6]=[CH:5]2.[CH:16]1(B(O)O)[CH2:18][CH2:17]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:16]1([C:2]2[C:3]([N+:13]([O-:15])=[O:14])=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[O:7][CH:6]=[CH:5]3)[CH2:18][CH2:17]1

Participants

8

Reactant 5

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 59515876HCID 59515876, compound

Product 1

HCID 59515813HCID 59515813, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×

Procedure

A microwave vial was charged with 6-bromo-5-nitro-1H-isochromen-1-one (500.00 mg, 0.0018516 mol), cyclopropylboronic acid (206.8 mg, 0.002407 mol), palladium acetate (21 mg, 0.000092 mol), tricyclohexylphosphine (52 mg, 0.00018 mol), potassium phosphate (1376 mg, 0.006481 mol), toluene (10 mL, 0.09 mol) and water. The mixture was heated using microwave irradiation at 100° C. for 30 minutes. The rection mixture was then diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried and evaporated. The resultant residue was purified by flash chromatography to afford the product. The product was used as such for the syntheses of 6-cyclopropyl compounds of this invention without further purification.

Workup

  1. temperatureThe mixture was heated
  2. custommicrowave irradiation at 100° C. for 30 minutes
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. customevaporated
  7. customThe resultant residue was purified by flash chromatography
  8. customto afford the product
  9. customwithout further purification

Sources & evidence

ORD record
ord-1d558a2899e64671a93f3413b0c4a695
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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