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

反応式

[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

参加物

反応物 2

HCID 9005Trimethyl orthoformate

HCID 86663126Tert-butyl 2-chloro-6-hydrazinoisonicotinate

生成物 1

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

反応条件

温度: 85 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード: ord-3cdf668da61b4004a33a2a6612719e03
出典データセット: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09238647B2

反応ノート

読み込み中…

参加物