Water → HCID 44217495, compound

HRID 1256624Notes

Reaction equation

HRID 1256624 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][OH:20])=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:21][O:22]C1C=CC(CCl)=CC=1.O>C1(C)C=CC=CC=1>[CH3:21][O:22][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH2:19][OH:20])=[N:11]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 10657568(1-Benzylindazol-3-yl)methanol

Product 1

HCID 44217495HCID 44217495, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 60% NaH (2.7 g; 0.07 mol) in toluene (200 ml) was added 1-benzyl-3-hydroxymethylindazole (10 g; 0.07 mol). The mixture was brought to boiling point and left stirring at reflux for 1 hour. 4-Methoxybenzyl chloride (14 g; 0.09 mol) was then added. The mixture was then stirred at reflux for 4 hours. The reaction was completed by cooling the mixture to room temperature and adding water (50 ml). The organic phase was separated out and washed, respectively, with 2N HCl (50 ml) and water (5×50 ml). The solvent was evaporated off under reduced pressure. The crude residue thus obtained was purified by flash chromatography on silica gel, using as eluent a 3/2 hexane/ethyl acetate mixture. The product obtained was crystallized from a 5/1 hexane/ethyl acetate mixture to give 5.1 g of [1-(4-methoxybenzyl)-1H-indazol-3-yl]methanol with a melting point of 95°-97° C.

Workup

  1. waitleft
  2. temperatureat reflux for 1 hour
  3. stirringThe mixture was then stirred
  4. temperatureat reflux for 4 hours
  5. customThe organic phase was separated out and
  6. washwashed
  7. customThe solvent was evaporated off under reduced pressure
  8. customThe crude residue thus obtained
  9. customwas purified by flash chromatography on silica gel
  10. customThe product obtained
  11. customwas crystallized from a 5/1 hexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-25563244f0d941c9813e523cdd3ba385
Source dataset
uspto-grants-2013_06
Patent number
US08461194B2

Reaction notes

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