1,2-Dimethoxyethane → 6-(Trifluoromethyl)-4-(3,4,5-trifluorophenyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 912818Notes

Reaction equation

HRID 912818 reaction equation
Br[C:2]1[C:10]2[NH:9][C:8](=[O:11])[NH:7][C:6]=2[CH:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[F:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[C:21]([F:24])[C:22]=1[F:23].C([O-])([O-])=O.[Na+].[Na+].O.C(COC)OC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.CCO>[F:13][C:12]([F:15])([F:14])[C:4]1[CH:3]=[C:2]([C:19]2[CH:18]=[C:17]([F:16])[C:22]([F:23])=[C:21]([F:24])[CH:20]=2)[C:10]2[NH:9][C:8](=[O:11])[NH:7][C:6]=2[CH:5]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 2734671(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride)HCID 2735133Sodium Carbonate MonohydrateHCID 115800214-Bromo-6-trifluoromethyl-1,3-dihydrobenzoimidazol-2-one

Product 1

HCID 116313296-(Trifluoromethyl)-4-(3,4,5-trifluorophenyl)-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 4-bromo-6-trifluoromethyl-1,3-dihydrobenzoimidazol-2-one (1.12 g, 4 mmol, Example 6a), 3,4,5-trifluorophenylboronic acid (1.1 g, 6 mmol, Lancaster), PdCl2(PPh3)2 (35 mg, 0.05 mmol, Aldrich), Na2CO3.H2O (1 g, 8 mmol), dimethoxyethane (7 mL), H2O (3 mL) and EtOH (2 mL) was subjected to microwave irradiation at 120° C. with stirring for 10 min. Water (10 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined organic phases were washed with brine (10 mL), dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel chromatography, eluting with 35% EtOAc/hexane to give the title compound as a light-brown solid. MS (ESI, pos. ion) m/z: 333 (M+1).

Workup

  1. customirradiation at 120° C.
  2. extractionthe mixture was extracted with EtOAc (2×20 mL)
  3. washThe combined organic phases were washed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with 35% EtOAc/hexane

Sources & evidence

ORD record
ord-e4118634e4034047844288537bd39b75
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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