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N,N'-Dimethylethylenediamine → 2-(4-Chlorophenyl)-5-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)furo[3,2-c]pyridin-4(5H)-one

HRID 60379
Notes
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Reaction equation

HRID 60379 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][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)=[CH:4][CH:3]=1.Br[C:19]1[CH:20]=[CH:21][C:22]2[N:26]=[C:25]([CH:27]3[CH2:29][CH2:28]3)[N:24]([CH3:30])[C:23]=2[CH:31]=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:19]4[CH:20]=[CH:21][C:22]5[N:26]=[C:25]([CH:27]6[CH2:28][CH2:29]6)[N:24]([CH3:30])[C:23]=5[CH:31]=4)[C:11](=[O:17])[C:10]=3[CH:9]=2)=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 580155582-(4-chlorophenyl)-5H-furo[3,2-c]pyridine-4-oneHCID 838254226-Bromo-2-cyclopropyl-1-methyl-1H-benzoimidazole

Product 1

HCID 1179496222-(4-Chlorophenyl)-5-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)furo[3,2-c]pyridin-4(5H)-oneYield 22%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 2-(4-chlorophenyl)furo[3,2-c]pyridin-4(5H)-one (100 mg), 6-bromo-2-cyclopropyl-1-methyl-1H-benzimidazole (123 mg), N,N′-dimethylethylenediamine (0.043 mL), copper(I) iodide (78.0 mg), potassium carbonate (169 mg) and DMSO (3.0 mL) was stirred at 190° 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 (37.3 mg) as a pale red solid.

Workup

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

Sources & evidence

ORD record
ord-0d33230c536c4ac384f6fa866e11d8a8
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440987B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes