Sodium Carbonate → HCID 117760071, compound

HRID 709830Notes

Reaction equation

[C:1]([CH2:3][CH2:4][C:5]1[C:6](OS(C(F)(F)F)(=O)=O)=[N:7][CH:8]=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])#[N:2].[F:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1>[C:1]([CH2:3][CH2:4][C:5]1[C:6]([C:25]2[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:24]=2[F:23])=[N:7][CH:8]=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])#[N:2]

Participants

Conditions

Temperature: 90 °C

Procedure

Under a nitrogen atmosphere, to a mixture of methyl 5-(2-cyanoethyl)-6-(((trifluoromethyl)sulfonyl)oxy)nicotinate (700 mg), 2-fluoro-5-methoxyphenylboronic acid (700 mg), tetrakis(triphenylphosphine)palladium (237 mg) and toluene (10 mL) was added 2 M aqueous sodium carbonate solution (3.1 mL), and the mixture was stirred at 90° C. for 1 hr. The reaction mixture was filtered, and the filtrate was diluted with ethyl acetate and THF. The diluted solution was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (635 mg) as a colorless oil.

Workup

filtrationThe reaction mixture was filtered
additionthe filtrate was diluted with ethyl acetate and THF
washThe diluted solution was washed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-653e933620734f978e82c2900c4b5315
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

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