Sodium Carbonate → 1-cyclopropyl-5-(3-fluoro-6H-dibenzo[b,e]oxepin-11-ylidenemethyl)-1,3-dihydro-benzoimidazol-2-one

HRID 2218762Notes

Reaction equation

HRID 2218762 reaction equation
[CH:1]1([N:4]2[C:8]3[CH:9]=[CH:10][C:11](B(O)O)=[CH:12][C:7]=3[NH:6][C:5]2=[O:16])[CH2:3][CH2:2]1.Br[CH:18]=[C:19]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH2:23][O:22][C:21]2[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:20]1=2.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[CH:1]1([N:4]2[C:8]3[CH:9]=[CH:10][C:11]([CH:18]=[C:19]4[C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=5[CH2:23][O:22][C:21]5[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:20]4=5)=[CH:12][C:7]=3[NH:6][C:5]2=[O:16])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6733469611-Bromomethylene-3-fluoro-6,11-dihydro-dibenzo[b,e]oxepineHCID 688898361-cyclopropyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid

Product 1

HCID 688923501-cyclopropyl-5-(3-fluoro-6H-dibenzo[b,e]oxepin-11-ylidenemethyl)-1,3-dihydro-benzoimidazol-2-oneYield 29.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Following procedures essentially as described in Example 219, mix 1-cyclopropyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid (120 mg, 0.55 mmol) (prepared essentially as described in Preparation 36), 11-bromomethylene-3-fluoro-6,11-dihydro-dibenzo[b,e]oxepine (E and Z mixture, 177 mg, 0.58 mmol), 2N Na2CO3 (0.7 mL), dioxane (8 mL) and (Ph3P)4Pd (38 mg, 0.033 mmol). Purify the crude product by column chromatography using THF/hexane to give 65 mg title compound as a gray powder.

Workup

  1. customprepared essentially
  2. customPurify the crude product by column chromatography

Sources & evidence

ORD record
ord-f1167c5cf956440dac9af051e563dbaf
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

Loading…