Water → HCID 86672713, compound

HRID 2369915Notes

Reaction equation

HRID 2369915 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[C:9]2[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1.O.FC(F)(F)C(O)=O>ClCCCl>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:6]2[N:5]([CH2:4][CH:3]=[O:2])[C:9]3[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=3[N:7]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86672712HCID 86672712, compound

Product 1

HCID 86672713HCID 86672713, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The solution of methyl 1-(2,2-dimethoxyethyl)-2-(4-fluorophenyl)-1H-benzo[d]imidazole-7-carboxylate (1.1 g, 3.1 mmol) from Step A above in 1,2-dichloroethane (5 mL) with water (3 mL) and trifluoroacetic acid (3 mL) was stirred at reflux for 2.5 h. The reaction mixture was concentrated under reduced pressure, the residue was diluted with methylene chloride, neutralized with saturated aqueous sodium bicarbonate, dried (Na2SO4), filtered, and concentrated under reduced pressure to afford methyl 2-(4-fluorophenyl)-1-(2-oxoethyl)-1H-benzo[d]imidazole-7-carboxylate (820 mg, 84%) as a clear oil: 1H NMR (500 MHz, CDCl3) δ 9.80 (s, 1H), 8.05 (d, J=8.0, Hz, 1H), 7.98 (d, J=7.5, Hz, 1H), 7.62 (dd, J=7.5, 5.0 Hz, 2H), 7.36 (t, J=8.0 Hz, 1H), 7.21 (t, J=7.5 Hz, 2H), 5.25 (s, 2H), 3.92 (s, 3H); MS (ESI+) m/z 313 (M+H).

Workup

  1. temperatureat reflux for 2.5 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with methylene chloride
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aa86582cf1434885932afa8085698c9f
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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