Toluene → HCID 59515813, compound

HRID 1161182Notes

Reaction equation

HRID 1161182 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×

Conditions

Temperature
100 °C

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 and heated at 100° C. for 30 minutes under microwaves. 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 obtain the product. The product was only 65% pure and was used to synthesize 6-cyclopropyl compounds of this invention without further purification. MS m/z=232.3 (M+H). 1H NMR (400 MHz, DMSO-d6): δ 8.22 (d, J=8.63 Hz, 1H), 7.69 (d, J=5.85 Hz, 1H), 7.33 (d, J=8.47 Hz, 1H), 651 (d, J+6.05 Hz, 1H), 1.96-1.89 (m, 1H), 1.19-1.14 (m, 2H, 0.97-0.93 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. customevaporated
  5. customThe resultant residue was purified by flash chromatography
  6. customto obtain the product
  7. customwithout further purification

Sources & evidence

ORD record
ord-9eb926808c8c4f448f975d37f120ae22
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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