Triacetoxyperiodinane → HCID 178481823, compound

HRID 1191222Notes

Reaction equation

HRID 1191222 reaction equation
[C:1]([C:5]1[C:6]([Cl:34])=[C:7]([C:11]2[NH:33][C:14]3[C:15]([O:29][CH2:30][CH2:31][OH:32])=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:28])([F:27])[F:26])=[CH:18][C:13]=3[N:12]=2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([C:5]1[C:6]([Cl:34])=[C:7]([C:11]2[NH:33][C:14]3[C:15]([O:29][CH2:30][CH:31]=[O:32])=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:28])([F:27])[F:26])=[CH:18][C:13]=3[N:12]=2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178481824HCID 178481824, compound

Product 1

HCID 178481823HCID 178481823, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-[2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy]-ethanol (230 mg, 0.466 mmol, prepared as described in Example 11, STEP F) in DCM (10 mL) at 0° C. was added Dess-Martin periodinane (395 mg, 0.931 mmol). The resulting mixture was warmed to room temperature and stirred for 2 h. The reaction was then quenched by adding aqueous 10% Na2S2O3 solution (20 mL). The resulting mixture was treated with EtOAc (50 mL) and washed with saturated NaHCO3 solution (20 mL), H2O (20 mL) and brine (20 mL). After drying with Na2SO4, the resulting solution was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (20:80-50:50 EtOAc/hexanes) to yield [2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy]-acetaldehyde as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ: 7.67 (dd, J=7.5, 1.9 Hz, 1H), 7.49-7.54 (m, 2H), 7.35-7.44 (m, J=7.3, 7.3, 7.3, 7.3, 1.6 Hz, 2H), 5.07 (t, J=4.9 Hz, 1H), 4.52 (dd, J=4.8, 1.5 Hz, 2H), 4.04 (s, 3H), 1.45 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calculated For C23H21F3N5O2: 492.1 (M+H), Measured: 492.1.

Workup

  1. customThe reaction was then quenched
  2. additionby adding aqueous 10% Na2S2O3 solution (20 mL)
  3. additionThe resulting mixture was treated with EtOAc (50 mL)
  4. washwashed with saturated NaHCO3 solution (20 mL), H2O (20 mL) and brine (20 mL)
  5. dry with materialAfter drying with Na2SO4
  6. concentrationthe resulting solution was concentrated in vacuo
  7. customthe residue was purified by flash chromatography on silica gel (20:80-50:50 EtOAc/hexanes)

Sources & evidence

ORD record
ord-2f6ba7054f4141aa86628fb38e755b68
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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