N,N'-Dimethylethylenediamine → 2-(5-Chloropyridin-2-yl)-5-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)furo[3,2-c]pyridin-4(5H)-one

HRID 60386Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][NH:12][C:11](=[O:17])[C:10]=3[CH:9]=2)=[N:6][CH:7]=1.[CH:18]1([C:21]2[N:22]=[C:23]3[CH:28]=[CH:27][C:26](I)=[CH:25][N:24]3[C:30]=2[CH3:31])[CH2:20][CH2:19]1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][N:12]([C:26]4[CH:27]=[CH:28][C:23]5[N:24]([C:30]([CH3:31])=[C:21]([CH:18]6[CH2:20][CH2:19]6)[N:22]=5)[CH:25]=4)[C:11](=[O:17])[C:10]=3[CH:9]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 220 °C

Procedure

A mixture of 2-(5-chloropyridin-2-yl)furo[3,2-c]pyridin-4(5H)-one (69.0 mg), 2-cyclopropyl-6-iodo-3-methylimidazo[1,2-a]pyridine (100 mg), N,N′-dimethylethylenediamine (0.030 mL), copper(I) iodide (53.3 mg), potassium carbonate (116 mg) and DMSO (3.0 mL) was heated at 220° C. for 1 hr under microwave irradiation. The reaction mixture was purified by silica gel column chromatography (NH, ethyl acetate/hexane), and the obtained solid was washed with ethyl acetate to give the title compound (2.30 mg) as a pale red solid.

Workup

customThe reaction mixture was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
washthe obtained solid was washed with ethyl acetate

Sources & evidence

ORD record: ord-c57caea9a1aa46e2a14203a1113e5586
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440987B2

Reaction notes

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