Triethyl orthoacetate → HCID 178475912, compound

HRID 2409029Notes

Reaction equation

HRID 2409029 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[C:10]([CH3:20])(OCC)([O:14]CC)[O:11]CC>CC(O)=O>[C:10]([OH:14])(=[O:11])[CH3:20].[Br:1][C:2]1[C:3]2[NH:9][C:10]([CH3:20])=[N:8][C:4]=2[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 78369Pyridine, 3-bromo-4,5-diamino-

Product 1

HCID 178475912HCID 178475912, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5-bromopyridine-3,4-diamine (20 g, 107 mmol) and (EtO)3CMe (100 mL) in HOAc (40 mL) was stirred and heated at reflux for 2 h then the EtOH was removed by distillation to afford a solid. The solid was filtered to give 15 g (52%) of 7-bromo-2-methyl-1H-imidazo-[4,5-c]pyridine acetate as a light yellow solid: MS (ESI) m/z: 212 [M+1]+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. customthe EtOH was removed by distillation
  4. customto afford a solid
  5. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-12df2d91aded43239c49e2e2ef402db6
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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