Bromine → HCID 10216464, compound

HRID 1866871Notes

Reaction equation

HRID 1866871 reaction equation
[CH2:1]([N:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=[CH:10][C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[Br:30]Br>C(O)(=O)C>[CH2:1]([N:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=[C:10]([Br:30])[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 101934871-benzyl-4-[(3-chlorobenzyl)oxy]-6-methylpyridin-2(1H)-one2×

Product 1

HCID 10216464HCID 10216464, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The product of example 38 (SC-83316), 1-benzyl-4-[(3-chlorobenzyl)oxy]-6-methylpyridin-2(1H)-one (0.91 mmol, 310 Mg), acetic acid (20 mL), and sodium acetate (0.91 mmol, 80 Mg) were stirred at room temperature when bromine (0.91 mmol, 145 Mg) was added. After stirring for one hour, the mixture was concentrated, dissolved in ethyl acetate, and washed successively with saturated aqueous sodium bicarbonate solution, brine, and water. After drying over magnesium sulfate and concentrating, the product was recrystallized from tetrahydrofuran/hexanes to yield a white solid. (240 Mg, 63%): 1H NMR (DMSO-d6/300 MHz) 7.6-7.0 (m, 10H), 6.5 (s, 1H), 5.33 (s, 2H), 5.33 (s, 2H), 2.3 (s, 3H). ESHRMS m/z 420.019 (M+H, C20H17NO2BrCl requires 420.019).

Workup

  1. additionwas added
  2. concentrationthe mixture was concentrated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed successively with saturated aqueous sodium bicarbonate solution, brine, and water
  5. dry with materialAfter drying over magnesium sulfate
  6. concentrationconcentrating
  7. customthe product was recrystallized from tetrahydrofuran/hexanes
  8. customto yield a white solid

Sources & evidence

ORD record
ord-7c4ca191a97e4fa8ab0447cafc8100f1
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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