2-(Methoxymethyl)benzeneboronic acid → 2-Chloro-5-(2-methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine
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]=1Participants
Procedure
226 a) 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)+. 226 b) N7-[5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester was prepared from 2-chloro-5-(2-methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (365.0 mg, 1.33 mmol) and 7-amino-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester (350.0 mg, 1.33 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (226.0 mg, 0.41 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a white foam (0.115 g, 17%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.64 (d, J=7.7 Hz, 1H), 7.59-7.42 (m, 5H), 7.39-7.13 (m, 3H), 7.00 (d, J=7.5 Hz, 1H), 6.92-6.88 (m, 1H), 4.35 (br s, 2H), 3.57-3.47 (m, 4H), 3.20 (s, 3H), 2.85-2.78 (m, 4H), 1.49 (s, 9H). MS=500, 501 (MH)+.
Sources & evidence
- ORD record
- ord-163044c40c504473a030e32b7935d8e7
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501936B2
Reaction notes
Loading…