Ethyl Acetate → HCID 178505686, compound

HRID 1512164Notes

Reaction equation

HRID 1512164 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7]([CH:9]=[CH:10][CH:11]3[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]3)=[N:8][C:4]=2[CH:3]=1.[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[C:23]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(COC)OC.[Pd](Cl)Cl.C(C1C=C[C-](P)C=1C(C)(C)C)(C)(C)C.[CH-]1C=CC=C1.[Fe+2].O>[F:17][C:14]1([F:18])[CH2:15][CH2:16][CH:11]([CH:10]=[CH:9][C:7]2[NH:6][C:5]3[CH:19]=[CH:20][C:2]([C:23]4[C:24]([C:28]([F:30])([F:31])[F:29])=[CH:25][CH:26]=[CH:27][C:22]=4[F:21])=[CH:3][C:4]=3[N:8]=2)[CH2:12][CH2:13]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 162171682-Fluoro-6-(trifluoromethyl)phenylboronic acidHCID 178506001HCID 178506001, compound

Product 1

HCID 178505686HCID 178505686, compound

Reagents, catalysts & solvents 3

HCID 131729813Di-t-butyl-phosphinoferrocene palladium chlorideCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 5-bromo-2-[2-(4,4-difluoro-cyclohexyl)-vinyl]-1H-benzimidazole (0.030 g, 0.088 mmol, prepared as in STEP F above), 2-fluoro-6-trifluoromethylphenyl boronic acid (0.040 g, 0.19 mmol), 1,1-bis(di-t-butyl-phosphinoferrocene palladium chloride (0.012 g, 0.018 mmol) in dimethoxyethane (2 mL) and 2M sodium carbonate (1.0 mL, 2 mmol) was stirred at 95° C. for 18 h. The resulting solution was cooled to room temperature and poured into a solution of ethyl acetate and water (1:1, 50 mL). The layers were separated. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica using ethyl acetate/hexanes 3:7 as eluent to yield 2-[2-(4,4-difluoro-cyclohexyl)-vinyl]-5-(2-fluoro-6-trifluoromethyl-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

Sources & evidence

ORD record
ord-c23cb18f734d479bb366fb41ea118daa
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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