Water → HCID 66876703, compound

HRID 1620026Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[N:13]=[CH:12]3)=[CH:7][C:6]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:5](OS(C(F)(F)F)(=O)=O)[CH:4]=1.[CH3:33]B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[N:13]=[CH:12]3)=[CH:7][C:6]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:5]([CH3:33])[CH:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of Intermediate 4 (23 mg) in DMF (1.0 ml) was added with methyl boronic acid (18 mg, Ald), sodium carbonate (30 mg), and PdCl2dppf·CH2Cl2 (8.0 mg, Ald), and stirred at 120° C. for 8 hours. The reaction mixture was added with water (30 ml), and ethyl acetate (30 ml×2) for extraction, and then successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine, the organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1), and the solvent was evaporated under reduced pressure by using a rotary evaporator to obtain the title compound (yield: 15 mg).

Workup

washsuccessively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine
customthe organic layer was dried
customthe solvent was evaporated under reduced pressure
customThe residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1)
customthe solvent was evaporated under reduced pressure
customa rotary evaporator

Sources & evidence

ORD record: ord-1258b366bcef4191bd537f6f164f5805
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772327B2

Reaction notes

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