Sodium Carbonate → HCID 118667048, compound

HRID 591534Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[C:9]2[CH:10]=[C:11](Br)[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])=[CH:13][C:8]=2[O:7][CH:6]=1.[C:26]([O-])([O-])=O.[Na+].[Na+].CB(O)O>COCCOC.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>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[C:9]2[CH:10]=[C:11]([CH3:26])[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])=[CH:13][C:8]=2[O:7][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To the mixture of methyl(5-bromo-6-((2,4-dichlorobenzyl)oxy)-1-benzofuran-3-yl)acetate (166 mg), aqueous 2M Na2CO3 (0.561 mL) and methylboronic acid (44.7 mg) in DME (3.7 mL) was added Pd(Ph3P)4 (43.2 mg). The mixture was stirred at 80° C. for 7 h. To the mixture was added methylboronic acid (44.8 mg) again. The mixture was stirred at 80° C. under nitrogen atmosphere over weekend. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (45.0 mg).

Workup

stirringThe mixture was stirred at 80° C. under nitrogen atmosphere over weekend
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record: ord-385468da503944de850a309a3bb83fab
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238639B2

Reaction notes

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