Water → 4-(4-bromo-1-(2,3-dichlorobenzyl)-2-methyl-1H-benzo[d]imidazol-6-yl)morpholine

HRID 1622450Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To the mixture of 4-(4-bromo-2-methyl-1H-benzo[d]imidazol-6-yl)morpholine (0.8 g, 2.70 mmol) in N,N-Dimethylformamide (DMF) (10 mL) was added 1-(bromomethyl)-2,3-dichlorobenzene (0.778 g, 3.24 mmol) and potassium carbonate (1.120 g, 8.10 mmol). The resulting reaction mixture was stirred at 90° C. for 4 h. It was cooled to room temperature and poured into water (100 mL). The aqueous mixture was extracted with DCM (100 mL×2). The combined organic phases were washed with Brine (100 mL) and concentrated. The crude material was purified on silica column (20˜90% EtOAc in Hexane) to give the product as solid (1.01 g, 82%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.55 (s, 3H) 3.03-3.18 (m, 4H) 3.79-3.89 (m, 4H) 5.35 (s, 2H) 6.31 (dd, J=7.83, 1.26 Hz, 1H) 6.54 (d, J=2.02 Hz, 1H) 7.08 (t, J=7.96 Hz, 1H) 7.17 (d, J=2.02 Hz, 1H) 7.45 (dd, J=8.06, 1.55 Hz, 1H); MS (ES+) m/e 453.8 [M+H]+.

Workup

customThe resulting reaction mixture
temperatureIt was cooled to room temperature
extractionThe aqueous mixture was extracted with DCM (100 mL×2)
washThe combined organic phases were washed with Brine (100 mL)
concentrationconcentrated
customThe crude material was purified on silica column (20˜90% EtOAc in Hexane)

Sources & evidence

ORD record: ord-39b898df4730445e95f5bb2b57af585d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778937B2

Reaction notes

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