Triacetoxyperiodinane → HCID 86691628, compound

HRID 624319Notes

Reaction equation

HRID 624319 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([O:25][CH:26]([CH3:28])[CH3:27])=[CH:18][C:11]=3[C:12]=2[C:13]2[NH:14][CH2:15][CH2:16][N:17]=2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CS(C)=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[C:19]([O:25][CH:26]([CH3:28])[CH3:27])=[CH:18][C:11]=3[C:12]=2[C:13]2[NH:17][CH:16]=[CH:15][N:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86691626HCID 86691626, compound

Product 1

HCID 86691628HCID 86691628, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 2-(2-(4-fluorophenyl)-5-isopropoxy-6-nitrobenzofuran-3-yl)-4,5-dihydro-1H-imidazole (1.0 g, 2.61 mmol) in DMSO (40 mL) at room temperature was added Dess-Martin periodinane (2.213 g, 5.22 mmol), and the stirring was continued at rt overnight. The reaction mixture was diluted with water. The product was extracted into EtOAc (100 mL×3), and the combined EtOAc extracts were washed with 10% NaHCO3 (100 mL×2) and brine, dried over Na2SO4 and then concentrated. The crude product was recrystallized from EtOAc and petroleum ethers to obtain 2-(2-(4-fluorophenyl)-5-isopropoxy-6-nitrobenzofuran-3-yl)-1H-imidazole as a yellow solid. Yield: 800 mg (80%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 12.46 (br. s., 1H) 8.33 (s, 1H) 7.85-8.08 (m, 2H) 7.16-7.60 (m, 5H) 4.79 (d, J=5.95 Hz, 1H) 1.15-1.47 (m, 6H). LCMS: (ES+) m/z=382.24 (M+H)+; Column—ACQUITY UPLC BEH C8 (50×2.1 mm; 1.7 μm); M phase A: 5 mM Ammonium Acetate:MeCN (95:5); M phase B: 5 mM Ammonium Acetate:MeCN (5:95)

Workup

  1. extractionThe product was extracted into EtOAc (100 mL×3)
  2. washthe combined EtOAc extracts were washed with 10% NaHCO3 (100 mL×2) and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was recrystallized from EtOAc and petroleum ethers

Sources & evidence

ORD record
ord-f345903c4f2e4180a9578e984410b463
Source dataset
uspto-grants-2016_04
Patent number
US09303020B2

Reaction notes

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