3-(Methylsulfonyl)phenylboronic acid → 8-(3-(Methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 1889742Notes

Reaction equation

HRID 1889742 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][S:13]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:14]>>[CH3:12][S:13]([C:16]1[CH:21]=[C:20]([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:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 468640698-Bromo-(1,2,4)triazolo(1,5-a)pyridin-2-amine

Product 1

HCID 575023748-(3-(Methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Procedure

8-(3-Methanesulfonyl-phenyl)-[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-(methanesulfonyl)phenyl boronic acid (1.0 g, 5.0 mmol) in a manner analogous to Step 2c. The reaction product was isolated as an off-white solid (0.99 g, 73%). MP=173-183° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.64-8.60 (m, 1H), 8.59 (t, J=1.6 Hz, 1H), 8.50-8.46 (m, 1H), 7.98-7.94 (m, 1H), 7.86-7.83 (m, 1H), 7.78 (dd, J=7.8, 7.8 Hz, 1H), 7.02 (dd, J=7.1, 7.1 Hz, 1H), 6.18 (s, 1H), 3.29 (S, 3H). MS=289 (MH)+. 13b) [8-(3-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine and [8-(3-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-phenyl-amine were prepared from 8-(3-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (100.0 mg, 0.3468 mmol) and 1-[2-(4-bromo-phenoxy)-ethyl]-pyrrolidine (90.0 L, 0.434 mmol) in a manner analogous to Step 2d. The title compound 8-(3-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine was isolated as a yellow foam (0.047 g, 28%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.66 (t, J=1.7 Hz, 1H), 8.47-8.44 (m, 1H), 8.39-8.35 (m, 1H), 8.01-7.97 (m, 1H), 7.26 (dd, J=7.8, 7.8 Hz, 1H), 7.68-7.65 (m, 1H), 7.54-7.48 (m, 2H), 6.99 (dd, J=7.0, 7.0 Hz, 1H), 6.96-6.92 (m, 2H), 6.91 (s, 1H), 4.11 (t, J=6.1 Hz, 2H), 3.13 (s, 3H), 2.91 (t, J=6.1 Hz, 2H), 2.68-2.58 (m, 4H), 1.85-1.78 (m, 4H). MS=478 (MH)+.

Sources & evidence

ORD record
ord-761198e778cb427e8c81051ff835996a
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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