Potassium Carbonate → N-(3-bromo-2-methylphenyl)-1-(2,2-diethoxyethyl)-1H-imidazole-2-carboxamide

HRID 661837Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH3:16])=[C:4]([NH:8][C:9]([C:11]2[NH:12][CH:13]=[CH:14][N:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH:25]([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28]>CN(C=O)C.O>[Br:1][C:2]1[C:3]([CH3:16])=[C:4]([NH:8][C:9]([C:11]2[N:15]([CH2:24][CH:25]([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])[CH:14]=[CH:13][N:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Step 2 A solution of N-(3-bromo-2-methylphenyl)-1H-imidazole-2-carboxamide (0.70 g, 2.499 mmol) in DMF (12.5 mL) was treated with potassium carbonate (0.794 g, 5.75 mmol) and 2-bromo-1,1-diethoxyethane (0.395 mL, 2.62 mmol). The suspension was heated at 100° C. overnight. The mixture was cooled to rt, diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 85:15 to 20:80 hexane-EtOAc) to provide N-(3-bromo-2-methylphenyl)-1-(2,2-diethoxyethyl)-1H-imidazole-2-carboxamide as a white solid (0.81 g, 82%). 1H NMR (400 MHz, DMSO-d6) δ 10.17 (1H, s), 7.51 (1H, d, J=2.6 Hz), 7.49 (1H, d, J=2.6 Hz), 7.44 (1H, d, J=1.1 Hz), 7.18 (1H, t, J=8.0 Hz), 7.10 (1H, d, J=1.1 Hz), 4.75 (1H, t, J=5.4 Hz), 4.52 (2H, d, J=5.3 Hz), 3.63 (2H, dq, J=9.7, 7.0 Hz), 3.35-3.44 (2H, m), 2.31 (3H, s), 1.05 (6H, t, J=7.0 Hz). Mass spectrum m/z 396, 398 (M+H)+.

Workup

temperatureThe mixture was cooled to rt
extractionextracted with EtOAc
washThe organic phase was washed with brine
customdried
concentrationconcentrated
customThe residue was purified by column chromatography (
washeluting with a gradient from 85:15 to 20:80 hexane-EtOAc)

Sources & evidence

ORD record: ord-462a3d84d3524a5394cd5643112e4a4b
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084620B2

Reaction notes

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