Bromoacetic Acid → HCID 67108567, compound

HRID 2074529Notes

Reaction equation

HRID 2074529 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH2:17][OH:18])=[N:9]2)=[CH:5][CH:4]=1.Br[CH2:22][C:23]([OH:25])=[O:24].[H-].[Na+]>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH2:17][O:18][CH2:22][C:23]([OH:25])=[O:24])=[N:9]2)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 44217495HCID 44217495, compound

Product 1

HCID 67108567HCID 67108567, compoundYield 62.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension containing [1-(4-methoxybenzyl)-1H-indazol-3-yl]methanol (6 g; 0.022 mol), bromoacetic acid (4 g; 0.03 mol) and 50% NaH (3 g; 0.066 mol) in THF (170 ml) was stirred at reflux for 72 hours. The reaction was then stopped by diluting with a suspension with water and ice (300 ml) and washing the aqueous phase with diethyl ether (3×150 ml). The aqueous phase was acidified with concentrated HCl. The solid thus formed was filtered off and purified by crystallization from isopropanol. 4.5 g of {[1-(4-methoxybenzyl)-1H-indazol-3-yl]methoxy}acetic acid were thus obtained.

Workup

  1. temperatureat reflux for 72 hours
  2. washwashing the aqueous phase with diethyl ether (3×150 ml)
  3. customThe solid thus formed
  4. filtrationwas filtered off
  5. custompurified by crystallization from isopropanol

Sources & evidence

ORD record
ord-0980a57c9ec54fb9aca8df153ec6ab9e
Source dataset
uspto-grants-2011_04
Patent number
US07919518B2

Reaction notes

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