Potassium Phosphate, Tribasic → HCID 66735589, compound

HRID 923210Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:8]2[N:9]([C:13]([C:16]#[C:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][N:15]=2)[CH:10]=[CH:11][CH:12]=1)(=O)=O.[CH3:24][S:25]([C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC>[CH3:24][S:25]([C:28]1[CH:34]=[CH:33][C:31]([NH:32][C:7]2[C:8]3[N:9]([C:13]([C:16]#[C:17][Si:18]([CH3:19])([CH3:20])[CH3:21])=[CH:14][N:15]=3)[CH:10]=[CH:11][CH:12]=2)=[CH:30][CH:29]=1)(=[O:26])=[O:27]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridin-8-yl trifluoromethanesulfonate (0.329 g, 0.91 mmol), 0.186 (1.09 mmol) of 4-(methylsulfonyl)aniline, 0.083 g (0.091 mmol) of Pd2(dba)2, 0.087 g (0.181 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, and 0.385 g (1.81 mmol) of potassium phosphate in 8 mL of DME was heated at 80° C. in a sealed tube overnight under an atmosphere of N2. Upon cooling to ambient temperature, the reaction mixture was concentrated and the crude product was purified by silica gel flash chromatography (triethylamine-treated silica gel; eluted with 0-80% EtOAc/hexanes) to provide 0.058 g of product: 384 m/z (M+H).

Workup

temperatureUpon cooling to ambient temperature
concentrationthe reaction mixture was concentrated
customthe crude product was purified by silica gel flash chromatography (triethylamine-treated silica gel; eluted with 0-80% EtOAc/hexanes)

Sources & evidence

ORD record: ord-486dfa68316d44989e5bd2070290d875
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278971B2

Reaction notes

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