2,3,6-Trifluoroaniline → ethyl 1-(4-fluorophenyl)-2-(((2,3,6-trifluorophenyl)amino)methyl)-1H-imidazole-5-carboxylate

HRID 2368485Notes

Reaction equation

HRID 2368485 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]2[CH:18]=O)=[CH:4][CH:3]=1.[F:20][C:21]1[C:27]([F:28])=[CH:26][CH:25]=[C:24]([F:29])[C:22]=1[NH2:23].[B][B][B][B][B][B][B][B][B][B]>C(O)(=O)C.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]2[CH2:18][NH:23][C:22]2[C:24]([F:29])=[CH:25][CH:26]=[C:27]([F:28])[C:21]=2[F:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5222832,3,6-TrifluoroanilineHCID 86677543ethyl 1-(4-fluorophenyl)-2-formyl-1H-imidazole-5-carboxylateHCID 178419135HCID 178419135, compound

Product 1

HCID 71117752ethyl 1-(4-fluorophenyl)-2-(((2,3,6-trifluorophenyl)amino)methyl)-1H-imidazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of ethyl 1-(4-fluorophenyl)-2-formyl-1H-imidazole-5-carboxylate (16) (150 mg, 0.57 mmol), 2,3,6-trifluoroaniline (60.4 μL, 0.57 mmol), decaborane (14 mg, 0.11), acetic acid (2 drops), and methanol (6 mL) was stirred at room temperature overnight. The reaction was concentrated and the residue was purified by flash column chromatography on silica gel (0-30% EtOAc in hexanes) to yield ethyl 1-(4-fluorophenyl)-2-(((2,3,6-trifluorophenyl)amino)methyl)-1H-imidazole-5-carboxylate (23).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by flash column chromatography on silica gel (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-dfbce6092f9649448ca2ce99c4f81893
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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