Potassium Carbonate → 1-(5-(2-(4-(2-(Azetidine-1-carbonyl)benzofuran-7-yl)piperazin-1-yl)ethyl)indolin-1-yl)ethanone

HRID 535670Notes

Reaction equation

[N:1]1([C:5]([C:7]2[O:8][C:9]3[C:15]([N:16]4[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.Br[CH2:23][CH2:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([C:34](=[O:36])[CH3:35])[CH2:29][CH2:28]2.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:1]1([C:5]([C:7]2[O:8][C:9]3[C:15]([N:16]4[CH2:17][CH2:18][N:19]([CH2:23][CH2:24][C:25]5[CH:26]=[C:27]6[C:31](=[CH:32][CH:33]=5)[N:30]([C:34](=[O:36])[CH3:35])[CH2:29][CH2:28]6)[CH2:20][CH2:21]4)=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 120 °C

Procedure

The reaction mixture of azetidin-1-yl(7-(piperazin-1-yl)benzofuran-2-yl)methanone (0.070 g, 0.25 mmol) (Example 45c), 1-(5-(2-bromoethyl)indolin-1-yl)ethanone (0.099 g, 0.37 mmol) and potassium carbonate (0.068 g, 0.49 mmol) in acetonitrile (1 mL) was heated by microwave irradiation at 120° C. for 15 min. The mixture was cooled and the solvent was removed in vacuo. The product was purified by flash chromatography (SiO2; DCM/MeOH; gradient 0-5%) to give the title compound. Yield: 0.056 g (48%).

Workup

temperatureThe mixture was cooled
customthe solvent was removed in vacuo
customThe product was purified by flash chromatography (SiO2; DCM/MeOH; gradient 0-5%)

Sources & evidence

ORD record: ord-6af78f3020ef4ea7b40e5ada870ca4f1
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859534B2

Reaction notes

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