Water → HCID 12312254, compound

HRID 2074524Notes

Reaction equation

HRID 2074524 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.[Cl:21]C1C=CC(CCl)=CC=1.O>C1(C)C=CC=CC=1>[Cl:21][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 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 10657568(1-Benzylindazol-3-yl)methanol

Product 1

HCID 12312254HCID 12312254, compoundYield 23%

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 the boiling point and left stirring at reflux for 1 hour. 4-chlorobenzyl chloride (14.4 g; 0.09 mol) was then added. The mixture was then stirred at reflux for 4 hours. The reaction was stopped 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 3/1 hexane/ethyl acetate mixture. The product obtained was crystallized from a 5/1 hexane/ethyl acetate mixture to give 4.4 g of [1-(4-chlorobenzyl)-1H-indazol-3-yl]methanol.

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-cbb47ddcc72a4bffa16650004d46e27f
Source dataset
uspto-grants-2011_04
Patent number
US07919518B2

Reaction notes

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