1,3-Propanediol → HCID 44217649, compound

HRID 76119Notes

Reaction equation

HRID 76119 reaction equation
[OH-].[Na+].[CH2:3]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19]Cl)=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:21]([OH:25])[CH2:22][CH2:23][OH:24]>>[CH2:3]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][O:24][CH2:23][CH2:22][CH2:21][OH:25])=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 104421,3-PropanediolHCID 14798Sodium HydroxideHCID 532606481-Benzyl-3-(chloromethyl)-1H-indazole

Product 1

HCID 44217649HCID 44217649, compound

Conditions

Temperature
130 °C

Procedure

To a solution of NaOH (2.8 g; 0.07 mol) in 1,3-propanediol (150 ml) stirred at room temperature was added 1-benzyl-3-chloromethylindazole, prepared as described in Example 2a of EP 382 276 (17.6 g; 0.07 mol). The solution was heated at 130° C. for 4 hours and then cooled to room temperature, and the solvent was evaporated off under reduced pressure. The residue was taken up in water (100 ml) and the product was extracted with ethyl acetate (3×100 ml). The combined organic phases were concentrated under reduced pressure and the crude residue obtained was purified by flash chromatography on silica gel, using as eluent a 1/1 hexane/ethyl acetate mixture. The product was purified by crystallization from an approximately 1/1 hexane/ethyl acetate mixture.

Workup

  1. customprepared
  2. temperaturecooled to room temperature
  3. customthe solvent was evaporated off under reduced pressure
  4. extractionthe product was extracted with ethyl acetate (3×100 ml)
  5. concentrationThe combined organic phases were concentrated under reduced pressure

Sources & evidence

ORD record
ord-115752aae62a4506a6c461fe1d7feac6
Source dataset
uspto-grants-2014_09
Patent number
US08835481B2

Reaction notes

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