Potassium Carbonate → HCID 178494667, compound

HRID 1488102Notes

Reaction equation

I[C:2]1[NH:6][C:5]([CH2:7][O:8][CH3:9])=[N:4][C:3]=1[CH3:10].[CH3:11][C:12]1[CH:21]=[C:20]([CH3:22])[C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:9][O:8][CH2:7][C:5]1[NH:6][C:2]([C:19]2[C:20]([CH3:22])=[CH:21][C:12]([CH3:11])=[C:13]([CH:18]=2)[C:14]([O:16][CH3:17])=[O:15])=[C:3]([CH3:10])[N:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Into a 50-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 5-iodo-2-(methoxymethyl)-4-methyl-1H-imidazole (compound 222.3, 400 mg, 1.59 mmol) in 1,4-dioxane (15 mL). Methyl 2,4-dimethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (compound 160.1, 510 mg, 1.76 mmol), a solution of potassium carbonate (662 mg, 4.79 mmol) in water (1 mL) and Pd(dppf)Cl2 (234 mg, 0.32 mmol) were added to the reaction. The reaction mixture was stirred overnight at 90° C. The solids were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography with dichloromethane/ethyl acetate (1:1) as eluent to furnish 220 mg (48%) of the title compound as a yellow solid.

Workup

customInto a 50-mL three neck round-bottom flask, which was purged
temperaturemaintained with an inert atmosphere of nitrogen
customThe solids were removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel chromatography with dichloromethane/ethyl acetate (1:1) as eluent

Sources & evidence

ORD record: ord-79779f827c8c49acb6f6e31217f8bb0f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428502B2

Reaction notes

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