Sodium Carbonate → HCID 86295885, compound

HRID 513240Notes

Reaction equation

HRID 513240 reaction equation
Br[C:2]1[C:3]([CH3:18])=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[O:6][CH:5]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:19][C:20]1[C:24](B(O)O)=[C:23]([CH3:28])[O:22][N:21]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[CH3:19][C:20]1[C:24]([C:2]2[C:3]([CH3:18])=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[O:6][CH:5]3[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:23]([CH3:28])[O:22][N:21]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 117599874HCID 117599874, compound

Product 1

HCID 86295885HCID 86295885, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-Bromo-4-methyl-3-phenyl-3H-isobenzofuran-1-one (100 mg, 0.33 mmol), 3,5-dimethylisoxazole-4-boronic acid (93 mg, 0.66 mmol, 2 eq.), 1N Na2CO3 (0.66 mL, 0.66 mmol) and Pd(PPh3)4 (62 mg, 0.033 mmol, 0.1 eq.) in dioxane (20 mL) is stirred at 90° C. for 16 hours. After cooled to room temperature, the mixture is evaporated in vacuo. The residue is purified by preparative-TLC using a petrol ether ethyl acetate mixture to afford the desired compound as a white solid.

Workup

  1. temperatureAfter cooled to room temperature
  2. customthe mixture is evaporated in vacuo
  3. customThe residue is purified

Sources & evidence

ORD record
ord-21c30aea06f646799f0842e2549c3a44
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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