Triethylamine → HCID 178519432, compound

HRID 2075258Notes

Reaction equation

HRID 2075258 reaction equation
[CH2:1]([C:8]1[CH:25]=[CH:24][C:11]2[NH:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][C:16]=3[F:23])=[N:14][C:10]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)Cl.CS(C)=O>CS(C)=O.CCOC(C)=O.O>[CH2:1]([C:8]1[CH:25]=[CH:24][C:11]2[NH:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][C:16]=3[F:23])=[N:14][C:10]=2[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 21912085Dimethylsulfoxide-dichloromethaneHCID 178519433HCID 178519433, compound

Product 1

HCID 178519432HCID 178519432, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4-(5-benzyl-1H-benzo[d]imidazol-2-yl)-3-fluorophenyl)methanol (0.055 g, 0.17 mmol) and triethylamine (0.12 mL, 0.83 mmol) in 1.5 mL 1:1 DCM/DMSO under nitrogen at 0° C. was added a solution of SO3*py (0.13 g, 0.83 mmol) in 0.75 mL DMSO. The reaction was allowed to stir for 2 h and was then diluted with EtOAc and water. The organic layer was washed 1× water, 1× brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by ISCO, 12 g, 0-40% EtOAc/hexanes, to give 4-(5-benzyl-1H-benzo[d]imidazol-2-yl)-3-fluorobenzaldehyde as a light yellow oil. MS (ESI) m/z: Calculated: 330.1; Observed: 331.0 (M++1).

Workup

  1. washThe organic layer was washed 1× water, 1× brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by ISCO, 12 g, 0-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-58f9615fd51a416994664adb2c836adc
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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