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

HRID 730759Notes

Reaction equation

HRID 730759 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(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

7

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 2734671(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride)HCID 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), Na2CO3H2O (1 g, 8 mmol), dimethoxyethane (7mL), 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-e79da49c9580495d853a9a891b4c90ad
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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