Triacetoxyperiodinane → HCID 79018099, compound

HRID 879411Notes

Reaction equation

HRID 879411 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([CH:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[OH:9])[CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 63893930HCID 63893930, compound

Product 1

HCID 79018099HCID 79018099, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (5-bromo-2-fluorophenyl)(pyridin-3-yl)methanol (3.75 g, 13.3 mmol) in DCM (50 mL) was added Dess-Martin periodinane (6.21 g, 14.6 mmol) portion-wise over several minutes. The reaction was then quenched with saturated 1:1 Na2S2O3/NaHCO3 solution (140 mL) and stirred until gas evolution ceased. The aqueous layer was extracted with DCM, dried over MgSO4, and purified by column chromatography (gradient 0 to 30% EtOAc in hexanes) to give the product. 1H NMR (400 MHz, CDCl3) δ 8.98 (s, 1H), 8.83 (dd, J=4.9, 1.7 Hz, 1H), 8.14 (dd, J=7.9, 0.6 Hz, 1H), 7.73 (dd, J=6.0, 2.5 Hz, 1H), 7.68 (ddd, J=8.7, 4.5, 2.6 Hz, 1H), 7.47 (dd, J=8.0, 4.9 Hz, 1H), 7.09 (t, J=9.0 Hz, 1H).

Workup

  1. customThe reaction was then quenched with saturated 1:1 Na2S2O3/NaHCO3 solution (140 mL)
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialdried over MgSO4
  4. custompurified by column chromatography (gradient 0 to 30% EtOAc in hexanes)
  5. customto give the product

Sources & evidence

ORD record
ord-cb130cbaa3204b69bc0217a986063600
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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