Triacetoxyperiodinane → HCID 86700469, compound

HRID 879656Notes

Reaction equation

HRID 879656 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]=[N: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:15]=[N:14][CH:13]=[N:12][CH:11]=2)=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 63894507HCID 63894507, compound

Product 1

HCID 86700469HCID 86700469, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (5-bromo-2-fluorophenyl)(pyrimidin-5-yl)methanol (2.42 g, 8.55 mmol) in DCM (40 mL) was added Dess-Martin periodinane (4 g, 9.4 mmol) portion-wise over several minutes. The reaction was then quenched with saturated 1:1 Na2S2O3/NaHCO3 solution (80 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 9.41 (s, 1H), 9.09 (d, J=1.6 Hz, 2H), 7.81 (dd, J=6.0, 2.6 Hz, 1H), 7.74 (ddd, J=8.8, 4.5, 2.6 Hz, 1H), 7.13 (t, J=9.1 Hz, 1H).

Workup

  1. customThe reaction was then quenched with saturated 1:1 Na2S2O3/NaHCO3 solution (80 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-211faa43a0ea462ca84a126a581d893e
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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