Hydrochloric Acid → 2-Bromo-[1,2,4]triazolo[1,5-a]pyridin-7-amine

HRID 1802248Notes

Reaction equation

HRID 1802248 reaction equation
[Br:1][C:2]1[N:18]=[C:5]2[CH:6]=[C:7]([NH:10]C(=O)OC(C)(C)C)[CH:8]=[CH:9][N:4]2[N:3]=1.Cl>ClCCl>[Br:1][C:2]1[N:18]=[C:5]2[CH:6]=[C:7]([NH2:10])[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67774787HCID 67774787, compound

Product 1

HCID 677745572-Bromo-[1,2,4]triazolo[1,5-a]pyridin-7-amineYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of tert-butyl 2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (5.19 g, 16.6 mmol) in dichloromethane (150 ml) and hydrochloric acid (5N in ether, 150 ml, 750 mmol) was stirred for 18 hours at 25° C. The solvents were evaporated, the residue was suspended in water (200 ml) and adjusted to pH=14 using sodium hydroxide 32%. The precipitated solid was filtered off, washed with water 4 times and dried in vacuo affording 2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylamine (2.39 g, 67.7&) as a light yellow solid. MS: m/z=213.0/215.1 (M+H+).

Workup

  1. customThe solvents were evaporated
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with water 4 times
  4. customdried in vacuo

Sources & evidence

ORD record
ord-dbfa4c9d0d864971ae737b17dd602155
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

Loading…