Potassium Carbonate → HCID 57550235, compound

HRID 1716841Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][CH:18]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[N:20]=2)=[CH:12][CH:11]=1.Br[CH2:26][CH:27]1[CH2:30][CH2:29][CH2:28]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH:27]1([CH2:26][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[C:2]2[C:10]2[CH:11]=[CH:12][C:13]([C:16]3[O:17][CH:18]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[N:20]=3)=[CH:14][CH:15]=2)[CH2:30][CH2:29][CH2:28]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of methyl {2-[4-(1H-benzimidazol-2-yl)phenyl]-1,3-oxazol-4-yl}carboxylate (200 mg, 0.62 mmol), bromomethylcyclobutane (140 mg, 0.94 mmol) and K2CO3 (103 mg, 0.75 mmol) in dry acetonitrile was heated to 120° C. with microwave irradiation for 1.5 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The resultant residue was dissolved in CH2Cl2, washed with water, dried over Na2SO4 and evaporated to dryness under reduced pressure. This residue was purified by column chromatography (silica, CH2Cl2:MeOH 98:2) to afford the title compound in 54% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 388 (MH+).

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
dissolutionThe resultant residue was dissolved in CH2Cl2
washwashed with water
dry with materialdried over Na2SO4
customevaporated to dryness under reduced pressure
customThis residue was purified by column chromatography (silica, CH2Cl2:MeOH 98:2)

Sources & evidence

ORD record: ord-73934f98c0ae4d5594261c3bded5440d
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803825B2

Reaction notes

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