(6-Methoxypyridin-3-yl)boronic acid → 8-(6-Methoxy-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

HRID 472261Notes

Reaction equation

HRID 472261 reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH2:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][N:15]=1>>[CH3:12][O:13][C:14]1[N:15]=[CH:16][C:17]([C:2]2[C:3]3[N:4]([N:8]=[C:9]([NH2:11])[N:10]=3)[CH:5]=[CH:6][CH:7]=2)=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 468640698-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine

Product 1

HCID 575023738-(6-Methoxy-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Procedure

8-(6-Methoxy-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was prepared from 8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (1.0 g, 4.7 mmol) and 2-methoxypyridine-5-boronic acid (1.0 g, 6.6 mmol) in a manner analogous to Step 2c. The product of the reaction was isolated as a tan solid (0.58 g, 51%). MP=157-158° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.91 (d, J=2.5 Hz, 1H), 8.54 (dd, J=6.6, 0.9 Hz, 1H), 8.44 (dd, J=8.7, 2.5 Hz, 1H), 7.73 (dd, J=7.6, 1.0 Hz, 1H), 6.97 (t, J=6.9 Hz, 1H), 6.96 (d, J=8.7 Hz, 1H), 6.12 (s, 2H), 3.92 (s, 3H). MS=242 (MH)+.

Sources & evidence

ORD record
ord-799a8e31dafa4fff98a05d75a5e1ed97
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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