Potassium Carbonate → HCID 59540723, compound

HRID 1677422Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[N:3]=[C:4]3[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one (60 mg, 0.21 mmol), 4-methoxyphenyl boronic acid (33 mg, 0.22 mmol), potassium carbonate (69 mg, 0.5 mmol), Pd(dppf)Cl2CH2Cl2 (13 mg, 0.016 mmol), 1.7 mL dioxane and 0.4 mL water was stirred at 150° C. in a microwave for 30 min. The resulting mixture was partitioned between ethyl acetate and water. The combined organic layers were dried over Na2SO4 and concentrated to give a dark brown solid. The crude product was purified by preparative thin layer chromatography using 90:9.5:0.5 CH2Cl2:MeOH:conc NH4OH as eluant. The resultant brown solid was washed with ethyl ether to provide 31 mg (50%) of 1-[2-(4-methoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a brown solid. MP 207-208° C., M+H 310.

Workup

customThe resulting mixture was partitioned between ethyl acetate and water
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated
customto give a dark brown solid
customThe crude product was purified by preparative thin layer chromatography
washThe resultant brown solid was washed with ethyl ether

Sources & evidence

ORD record: ord-cd59d3365a6b467fb267c2ba83427eb3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008298B2

Reaction notes

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