3-Pyridinylboronic acid → 8-Pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

HRID 472259Notes

Reaction equation

HRID 472259 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.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1>>[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([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:13]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 468640698-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine

Product 1

HCID 575023718-Pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Procedure

8-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 3-pyridylboronic acid (0.81 g, 6.6 mmol) in a manner analogous to Step 2c. The product of the reaction was isolated as a white solid (0.92 g, 93%). MP=185-187° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.28 (d, J=2.1 Hz, 1H), 8.62-8.58 (m, 2H), 8.49 (ddd, J=8.1, 1.8, 1.8 Hz, 1H), 7.82 (dd, J=7.4, 0.7 Hz, 1H), 7.53 (dd, J=8.0, 4.7 Hz, 1H), 7.01 (t, J=7.0 Hz, 1H), 6.18 (br s, 2H). MS=212 (MH)+.

Sources & evidence

ORD record
ord-f97201b391bb432792d0816f829a5f52
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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