Morpholine → 2-(2,6-Dimethyl-4-morpholin-4-yl-phenyl)-3H-benzoimidazole-5-carboxylic acid methyl ester

HRID 1513221Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:29]=[CH:28][C:8]2[N:9]=[C:10]([C:12]3[C:17]([CH3:18])=[CH:16][C:15](OS(C(F)(F)F)(=O)=O)=[CH:14][C:13]=3[CH3:27])[NH:11][C:7]=2[CH:6]=1)=[O:4].[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.CCCCCCC.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]>[CH3:1][O:2][C:3]([C:5]1[CH:29]=[CH:28][C:8]2[N:9]=[C:10]([C:12]3[C:13]([CH3:27])=[CH:14][C:15]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[CH:16][C:17]=3[CH3:18])[NH:11][C:7]=2[CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 2.4 g of 2-(2,6-Dimethyl-4-trifluoromethanesulfonyloxy-phenyl)-3H-benzoimidazole-5-carboxylic acid methyl ester in 6 ml of toluene was added 4 ml of morpholine, 280 mg of Pd2(dba)3, 400 mg of P(biphenyl)t -Bu2 and 2.0 g of K3PO4. The reaction vessel sealed and heated at 80° C. overnight. The reaction was cooled to room temperature and diluted with water and heptane. The resulting precipitates were collected by filtration, washed with water and dried to afford the title compound. LCMS retention T=1.14 min, m/z=366.2, Method 10.

Workup

customThe reaction vessel sealed
temperatureThe reaction was cooled to room temperature
customThe resulting precipitates
filtrationwere collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-f028f19ac43b4fe192fb6ae8f3a09cce
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217065B2

Reaction notes

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