Triacetoxyperiodinane → HCID 22050686, compound

HRID 1867070Notes

Reaction equation

HRID 1867070 reaction equation
[Br:1][C:2]1[C:3](=[O:28])[N:4]([C:19]2[CH:24]=[C:23]([CH2:25][OH:26])[CH:22]=[CH:21][C:20]=2[CH3:27])[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CC#N.C(Cl)Cl>[Br:1][C:2]1[C:3](=[O:28])[N:4]([C:19]2[CH:24]=[C:23]([CH:22]=[CH:21][C:20]=2[CH3:27])[CH:25]=[O:26])[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 22050887HCID 22050887, compound

Product 1

HCID 22050686HCID 22050686, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Conditions

Temperature
0 °C

Procedure

3-bromo-4-[(2,4-difluorobenzyl)oxy]-1-[5-(hydroxymethyl)-2-methylphenyl]-6-methylpyridin-2(1H)-one (1.5 g, 3.33 mmol) was dissolved in 75% CH3CN/CH2Cl2 (20 ml) and cooled to 0° C. Dess-Martin Periodinane (2.8 g, 6.66 mmol) was added and the reaction stirred for four hours. At this time, the reaction was quenched with 5% sodium bisulfite (aq.). The product was extracted with ethyl acetate. The combined organic extracts were then washed with saturated NaHCO3 (aq.). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over Na2SO4, filtered, and concentrated. The resulting residue was taken up in diethyl ether and the precipitate was collected on a filter pad and washed with more diethyl ether to yield a white solid (1.35 g, 91%). 1H NMR (300 MHz, CDCl3) δ 10.00 (s, 1H), 7.91 (dd, J=7.65, 1.61 Hz, 1H), 7.65 (m, 2H), 7.57 (d, J=7.85 Hz, 1H), 7.03 (m, 1H), 6.95 (ddd, J=12.69, 8.86, 2.62 Hz, 1H), 6.19 (s, 1H), 5.31 (s, 2H), 2.20 (s, 3H), 1.96 (s, 3H); ES-MS m/z 448 (M+H). ES-HRMS m/z 448.0347 (M+H calcd for C21H17BrF2NO3 requires 448.0354).

Workup

  1. customAt this time, the reaction was quenched with 5% sodium bisulfite (aq.)
  2. extractionThe product was extracted with ethyl acetate
  3. washThe combined organic extracts were then washed with saturated NaHCO3 (aq.)
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe precipitate was collected on a filter pad
  9. washwashed with more diethyl ether

Sources & evidence

ORD record
ord-930a956c2f2b4fd682563dfc6e842287
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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