Water → CGP-47292 methyl ester

HRID 541034Notes

Reaction equation

HRID 541034 reaction equation
[N:1]([CH2:4][C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[F:12])=[N+:2]=[N-:3].Br[C:14](=[CH2:19])[C:15]([O:17][CH3:18])=[O:16].O>C(O)(C)(C)C>[F:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([F:11])[C:5]=1[CH2:4][N:1]1[CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 229990Methyl 2-bromoacrylateHCID 108883232-(Azidomethyl)-1,3-difluorobenzene

Product 1

HCID 22716778CGP-47292 methyl ester

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
77.5 °C

Procedure

A mixture of 2-(azidomethyl)-1,3-difluorobenzene in t-butanol prepared as per example 2, methyl 2-bromoacrylate (120 gms) and water (200 ml) were heated to 75-80° C. The contents was stirred at 75-80° C. for 24 hours. After the completion of reaction, the reaction mixture was cooled to room temperature. The solid obtained was filtered and then crude mass was added to cyclohexane (240 ml) and the mixture was stirred at room temperature for 2 hours. The solid was filtered and washed with cyclohexane (50 ml). The product was dried for 2 hours to give methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate. Yield: 120 gms

Workup

  1. customAfter the completion of reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customThe solid obtained
  4. filtrationwas filtered
  5. additioncrude mass was added to cyclohexane (240 ml)
  6. stirringthe mixture was stirred at room temperature for 2 hours
  7. filtrationThe solid was filtered
  8. washwashed with cyclohexane (50 ml)
  9. customThe product was dried for 2 hours

Sources & evidence

ORD record
ord-f9f4a9e1f2b049fba33409a8d9ac7437
Source dataset
uspto-grants-2014_10
Patent number
US08871945B2

Reaction notes

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