2-(Methoxymethyl)benzeneboronic acid → 2-Chloro-5-(2-methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 472527

Reaction equation

HRID 472527 reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([Cl:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O>>[Cl:11][C:9]1[N:10]=[C:3]2[CH:2]=[CH:7][CH:6]=[C:5]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][O:13][CH3:12])[N:4]2[N:8]=1

Participants

3

Reactant 2

HCID 37594082-(Methoxymethyl)benzeneboronic acidHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 674815372-Chloro-5-(2-methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine

Procedure

2-Chloro-5-(2-methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine was prepared from 8-bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine (546.0 mg, 2.35 mmol) and 2-(methoxymethyl)phenylboronic acid (545.0 mg, 3.29 mmol) in a manner analogous to Example 2c. Product was isolated as a white solid (0.384 g, 60%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.72-7.41 (m, 6H), 7.09-7.05 (m, 1H), 4.30 (br s, 2H), 3.16 (s, 3H). MS=274 (MH)+.

Sources & evidence

ORD record
ord-a77769b711fd4e91b863754c4ee7948c
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Linked notes

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