indium(III)chloride → 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1 H-1,2,4-triazol-3-yl)phenyl)cyclohexanone

HRID 924287Notes

Reaction equation

HRID 924287 reaction equation
[Cl-].[In+3].[Cl-].[Cl-].[C:5]12([C:12]3[CH:17]=[CH:16][C:15]([C:18]4[N:22]=[CH:21][N:20]([C:23]5[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=5)[N:19]=4)=[CH:14][CH:13]=3)[O:11][CH:10]1[CH2:9][CH2:8][CH2:7][CH2:6]2>C1COCC1.C(OCC)C>[F:33][C:30]([F:31])([F:32])[O:29][C:26]1[CH:25]=[CH:24][C:23]([N:20]2[CH:21]=[N:22][C:18]([C:15]3[CH:16]=[CH:17][C:12]([CH:5]4[CH2:6][CH2:7][CH2:8][CH2:9][C:10]4=[O:11])=[CH:13][CH:14]=3)=[N:19]2)=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 159675indium(III)chlorideHCID 904128703-(4-(7-oxabicyclo[4.1.0]heptan-1-yl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

Product 1

HCID 904122422-(4-(1-(4-(trifluoromethoxy)phenyl)-1 H-1,2,4-triazol-3-yl)phenyl)cyclohexanoneYield 49.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of indium chloride (1.259 g, 5.69 mmol) in 15 mL of dry THF in a 100 mL flask was added a solution of 3-(4-(7-oxabicyclo[4.1.0]heptan-1-yl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (CB54) (1.14 g, 2.85 mmol) in dry tetrahydrofuran (10 mL). Stirring was continued under nitrogen for 24 hours, then the solution was diluted with diethyl ether (50 mL) and washed with water, dried, and concentrated in vacuo. Purification by flash column chromatography using 0-60% ethyl acetate/hexanes as eluent provided the title compound as a white solid (0.566 g, 35%): 1H NMR (400 MHz, CDCl3) δ 1H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 8.16 (dd, J=8.6, 2.1 Hz, 2H), 7.83-7.72 (m, 2H), 7.43-7.33 (m, 2H), 7.30-7.21 (m, 2H), 3.68 (dd, J=12.2, 5.4 Hz, 1H), 2.61-2.41 (m, 2H), 2.37-2.24 (m, 1H), 2.23-1.92 (m, 3H), 1.85-1.60 (m, 2H); 19F NMR (376 MHz, CDCl3) δ −58.03; ESIMS m/z 402 ([M+H]+).

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-4eac5b3c6de645ae8b552862b5105819
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

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