1-Bromo-2-Chloroethane → 5-(2-chloroethoxy)-2-methyl-3-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}pyrazolo[1,5-a]pyridine

Reaction equation

Br[CH2:2][CH2:3][Cl:4].[CH3:5][C:6]1[C:15]([C:16]2[S:17][C:18]([C:27]3[N:31]=[CH:30][N:29]([CH:32]4[CH2:37][CH2:36][CH2:35][CH2:34][O:33]4)[N:28]=3)=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:20]=2)=[C:9]2[CH:10]=[C:11]([OH:14])[CH:12]=[CH:13][N:8]2[N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[Cl:4][CH2:3][CH2:2][O:14][C:11]1[CH:12]=[CH:13][N:8]2[N:7]=[C:6]([CH3:5])[C:15]([C:16]3[S:17][C:18]([C:27]4[N:31]=[CH:30][N:29]([CH:32]5[CH2:37][CH2:36][CH2:35][CH2:34][O:33]5)[N:28]=4)=[C:19]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:20]=3)=[C:9]2[CH:10]=1

Participants

Reactant 3

HCID 78491-Bromo-2-Chloroethane

HCID 10796Cesium carbonate

HCID 178433751HCID 178433751, compound

Product 1

HCID 668553945-(2-chloroethoxy)-2-methyl-3-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}pyrazolo[1,5-a]pyridineYield 93.6%

Procedure

The title compound has been prepared according to the similar manner described in 85-B (ii) from 1-bromo-2-chloroethane (163 μL, 1.96 mmol), 2-methyl-3-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}pyrazolo[1,5-a]pyridin-5-ol (300 mg, 0.654 mmol) obtained in Example 31-B-(i) and cesium carbonate (639 mg, 1.96 mmol). The crude product has been roughly purified by simple filtration through silica gel pad (5 g) and then washed with diethyl ether (20 mL) to give title compound (319 mg, 93%) as a colorless solid.