Benzyl Bromide → HCID 67281599, compound

HRID 1187489Notes

Reaction equation

HRID 1187489 reaction equation
[OH-].[Na+].[OH:3][C:4]1[C:9](=[O:10])[CH:8]=[C:7]([CH:11]([OH:16])[C:12]([F:15])([F:14])[F:13])[N:6]([CH3:17])[C:5]=1[CH2:18][OH:19].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO>[CH2:20]([O:3][C:4]1[C:9](=[O:10])[CH:8]=[C:7]([CH:11]([OH:16])[C:12]([F:15])([F:13])[F:14])[N:6]([CH3:17])[C:5]=1[CH2:18][OH:19])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 67282310HCID 67282310, compound

Product 1

HCID 67281599HCID 67281599, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 6.00 N sodium hydroxide solution (785 μL, 4.71 mmol) was added to a suspension of 3-hydroxy-2-hydroxymethyl-1-methyl-6-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (1.08 g, 4.26 mmol) in methanol (5 mL). Benzyl bromide (650 μL, 5.46 mmol) was added to the clear solution, and the resulting solution was heated to reflux for 45 min Some solid had separated out in the solution. Analysis of the reaction mixture using HPLC Method 1 (Example 24) indicated that the starting material was consumed. The reaction mixture was allowed to cool down to room temperature, and the first crop of solid product was collected by suction filtration, and washed with acetonitrile. The title compound was thus obtained as a solid product (1.11 g, 76% yield, HPLC Method 1 (Example 24), RT=12.6 min, HPLC purity (peak percent area): 99% at λ=280 nm). 1H NMR (DMSO-d6+D2O) δ ppm: 7.36 (m, 5H), 6.59 (s, 1H), 5.53 (q, J=6.5 Hz, 1H), 5.01 (s, 2H), 4.58 (s, 2H), 3.72 (s, 3H).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 45 min Some solid
  3. customhad separated out in the solution
  4. customwas consumed
  5. filtrationthe first crop of solid product was collected by suction filtration
  6. washwashed with acetonitrile

Sources & evidence

ORD record
ord-713edbff81f948ada56d66a6ca032137
Source dataset
uspto-grants-2014_03
Patent number
US08673943B2

Reaction notes

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