Bromoacetic Acid → HCID 44217165, compound

HRID 76118Notes

Reaction equation

HRID 76118 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:16][OH:17])=[N:8]2)=[CH:4][CH:3]=1.Br[CH2:21][C:22]([OH:24])=[O:23].[H-].[Na+]>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:16][O:17][CH2:21][C:22]([OH:24])=[O:23])=[N:8]2)=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 44217648HCID 44217648, compound

Product 1

HCID 44217165HCID 44217165, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension containing [1-(4-fluorobenzyl)-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 g of {[1-(4-fluorobenzyl)-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-e37ccea55691465fb16e2e49f331aaa8
Source dataset
uspto-grants-2014_09
Patent number
US08835481B2

Reaction notes

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