Acetamide → HCID 57785796, compound

HRID 1628789Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][C:14]4[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:15]=4[N:11]3[CH2:10][CH2:9]2)=[C:4]([Cl:26])[CH:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+].[C:75]([NH2:78])(=[O:77])[CH3:76]>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCCC1>[Cl:26][C:4]1[CH:3]=[C:2]([NH:78][C:75](=[O:77])[CH3:76])[CH:7]=[CH:6][C:5]=1[N:8]1[C:12]2=[N:13][C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:15]=3[N:11]2[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1-(4-bromo-2-chlorophenyl)-8-chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole (56.5 mg, 0.125 mmol), xantphos (10.8 mg, 0.0188 mmol), tris(dibenzylideneacetone)dipalladium (5.7 mg, 0.00625 mmol), cesium carbonate (61.1 mg, 0.188 mmol), acetamide (14.8 mg, 0.250 mmol) and tetrahydrofuran (0.5 mL) was stirred at 70° C. for 5 hrs. After cooling, the mixture was diluted with ethyl acetate and the precipitate was removed by filtration and the filtrate was concentrated in vacuo to give the title compound as an amorphous (3.8 mg, 0.0088 mmol, 7%).

Workup

temperatureAfter cooling
customthe precipitate was removed by filtration
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-38593d93f2e946bfab28221f62bc4c93
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785460B2

Reaction notes

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