Cesium carbonate → HCID 86296098, compound

HRID 513244Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([CH3:18])[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.[Cs+].[Cs+]>O1CCOCC1.O.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[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6](=[O:11])[C:5]3([CH3:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:23]([CH3:28])[O:22][N:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-Bromo-3-methyl-3-phenyl-1,3-dihydro-indol-2-one (602 mg, 2 mmol), compound 3,5-dimethylisoxazole-4-boronic acid (564 mg, 4 mmol), Pd(PPh3)4 (440 mg, 0.4 mmol) and Cs2CO3 (1.624 g, 5 mmol) in dioxane (10 mL) and H2O (5 mL) is stirred at 80° C. under nitrogen for 20 hours. The mixture is poured into water (20 mL) and extracted with ethyl acetate (20 mL×3). The combined organic phase is washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue is purified by chromatography on silica gel (ethyl acetate:petroleum ether=1:2) to give the desired compound.

Workup

extractionextracted with ethyl acetate (20 mL×3)
washThe combined organic phase is washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue is purified by chromatography on silica gel (ethyl acetate:petroleum ether=1:2)

Sources & evidence

ORD record: ord-6c38f7867134472681f5aad3ceba67b7
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102684B2

Reaction notes

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