2-Isopropoxyphenylboronic acid → 2-Chloro-8-(2-isopropoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 1890037Notes

Reaction equation

HRID 1890037 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.[CH:12]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O)([CH3:14])[CH3:13].C(OC(N1CCC2C=CC(N)=CC=2CC1)=O)(C)(C)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[Cl:11][C:9]1[N:10]=[C:3]2[C:2]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][CH:12]([CH3:14])[CH3:13])=[CH:7][CH:6]=[CH:5][N:4]2[N:8]=1

Participants

5

Reactant 4

HCID 50840992-Isopropoxyphenylboronic acidHCID 11402789Tert-butyl 7-amino-4,5-dihydro-1H-benzo[D]azepine-3(2H)-carboxylateHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 674814482-Chloro-8-(2-isopropoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridine

Procedure

2-Chloro-8-(2-isopropoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridine was prepared from 8-bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine and 2-isopropoxyphenylboronic acid in a manner analogous to Example 2c (0.24 g, 40%). MS=288 (MH)+. 302b) 7-[8-(2-Isopropoxy-phenyl]-[1,2,4]triazolo[1,5a]pyridine-2-ylamino]-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester was prepared from 2-chloro-8-(2-isopropxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridine and 7-amino-1,2,4,5-tetrahydro-3-benzazepin-3-carboxylic acid tert-butyl ester with 2,2′-bis-dicyclohexylphosphanyl-biphenyl as the ligand in a manner analogous to Example 2d (0.35 g, 82%). MP=112-114° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.54 (s, 1H), 8.73 (d, 1H), 7.60 (m, 2H), 7.48 (s, 1H), 7.38 (m, 2H), 7.17 (m, 1H), 7.05 (m, 3H), 4.57 (m, 1H), 3.44 (m, 4H), 2.80 (m, 4H), 1.41 (s, 9H), 1.15 (m, 6H). MS=514 (MH)+.

Sources & evidence

ORD record
ord-aea85a7c6051442d930db9518d1f5ae9
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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