Trimethyl orthoformate → Tert-butyl 5-chloro-[1,2,4]triazolo[4,3-a]pyridine-7-carboxylate

HRID 592303Notes

Reaction equation

HRID 592303 reaction equation
[CH:1](OC)(OC)OC.[Cl:8][C:9]1[CH:10]=[C:11]([CH:19]=[C:20]([NH:22][NH2:23])[N:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>>[Cl:8][C:9]1[N:21]2[CH:1]=[N:23][N:22]=[C:20]2[CH:19]=[C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH:10]=1

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 86663126Tert-butyl 2-chloro-6-hydrazinoisonicotinate

Product 1

HCID 77231272Tert-butyl 5-chloro-[1,2,4]triazolo[4,3-a]pyridine-7-carboxylateYield 43.7%

Conditions

Temperature
85 °C

Procedure

Trimethyl orthoformate (100 mL, 903 mmol) was added neat to tert-butyl 2-chloro-6-hydrazinoisonicotinate (10.0 g, 41.0 mmol). The mixture was heated to 85° C. After 5 h, the mixture was cooled to ambient temperature and concentrated. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) gave the title compound (4.55 g): LC-MS [M+1]=254.1.

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-3cdf668da61b4004a33a2a6612719e03
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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