Hydrogen Bromide → HCID 67481387, compound

2,8-Dibromo-[1,2,4]triazolo[1,5-a]pyridine was prepared from 8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (0.50 g, 2.3 mmol) with copper(II) bromide (0.140 g, 0.627 mmol) and 48% aqueous hydrobromic acid (5 mL, 40 mmol) in a manner analogous to Step 68a. the reaction product was isolated as a pale yellow solid (0.55 g, 85%). MP=150-151° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.99 (d, J=6.7 Hz, 1H), 8.08 (d, J=7.7 Hz, 1H), 7.20 (t, J=7.4 Hz, 1H). MS=276, 278, 280 (MH)+. 69b) N(2),N(8)-Bis-(2-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2,8-diamine was prepared from 2,8-dibromo-[1,2,4]triazolo[1,5-a]pyridine (100.0 mg, 0.3611 mmol) and 2-methanesulfonyl-phenylamine; hydrochloride (90.0 mg, 0.433 mmol) with 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (42.0 mg, 0.0726 mmol) as the ligand in a manner analogous to Step 2d. The title compound was isolated as an off-white solid (0.022 g, 13%). MP=271-273° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 9.17 (s, 1H), 8.71 (d, J=9.3 Hz, 1H), 8.51 (s, 1H), 8.14 (d, J=5.1 Hz, 1H), 8.00 (d, J=8.0 Hz, 1H), 7.92 (d, J=8.4 Hz, 1H), 7.65 (t, J=7.0 Hz, 1H), 7.59-7.50 (m, 2H), 7.31 (d, J=6.9 Hz, 1H), 7.18-7.08 (m, 2H), 6.88 (t, J=7.0 Hz, 1H), 3.15 (s, 3H), 3.11 (s, 3H). MS=458 (MH)+.

ORD record

ord-d32b5f94635845e4af8a9fc93ddb6b96

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501936B2