Ethyl Acetate → HCID 178506367, compound

HRID 1512157Notes

Reaction equation

HRID 1512157 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7]([CH:9]=[CH:10][CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[N:8][C:4]=2[CH:3]=1.[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(COC)OC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH:11]1([CH:10]=[CH:9][C:7]2[NH:6][C:5]3[CH:17]=[CH:18][C:2]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[O:21][C:20]([F:19])([F:32])[F:31])=[CH:3][C:4]=3[N:8]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27772042-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 178419326HCID 178419326, compound

Product 1

HCID 178506367HCID 178506367, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 5-bromo-2-(2-cyclohexyl-vinyl)-1H-benzimidazole (1.2 g, 3.9 mmol, prepared as in STEP B above), 2-trifluoromethoxyphenylboronic acid (1.6 g, 7.8 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.752 g, 0.92 mmol) in dimethoxyethane (32 mL) and 2M sodium carbonate (16 mL, 32 mmol) was stirred at 95° C. for 18 h. The resulting solution was cooled to room temperature and poured into a mixture of ethyl acetate and water (1:1, 50 mL). The layers were separated and the organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica using 3:7 v/v ethyl acetate/hexanes to yield 2-(2-cyclohexyl-vinyl)-5-(2-trifluoromethoxy-phenyl)-1H-benzimidazole.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica using 3:7 v/v ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fa023f224ceb449495ceac7e6f1dd074
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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