Cesium carbonate → 5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-3-phenyl-1,2,3-triazolo[4,5-c]isoquinoline

HRID 1017639Notes

Reaction equation

[C:1]1([N:7]2[C:11]3=[N:12][C:13](=[O:20])[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]3=[N:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[CH3:28][N:29]1[C:33]([CH2:34]Cl)=[N:32][CH:31]=[N:30]1>CN(C=O)C.O>[CH3:28][N:29]1[C:33]([CH2:34][O:20][C:13]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:10]3[N:9]=[N:8][N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:11]=3[N:12]=2)=[N:32][CH:31]=[N:30]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-phenyl-1,2,3-triazolo[4,5-c]isoquinolin-5-one (0.10 g, 0.38 mmol), cesium carbonate (0.33 g, 1.0 mmol) and 2-methyl-3-chloromethyl-1,2,4-triazole hydrochloride (0.08 g, 0.48 mmol) in dry DMF (2 ml) was stirred at 60° C. for 5 h. The mixture was diluted with water (20 ml) and the white solid was collected, washing with water (10 ml) and diethyl ether (10 ml). The solid was dried to give 5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-3-phenyl-1,2,3-triazolo[4,5-c]isoquinoline (0.093 g, 68%), m.p. 188-190° C. Found: C, 63.48; H, 4.19; N, 27.14. C19H15N7O.0.1(H2O) requires C, 63.54; H, 4.27; N, 27.30. δH (360 MHz; CDCl3) 3.99 (3H, s), 5.83 (2H, s), 7.48-7.53 (1H, m), 7.61-7.70 (3H, m), 7.94-7.98 (2H, m), 8.20-8.22 (2H, m), 8.37 (1H, d, J=8) and 8.69 (1H, d, J=8); m/z (ES+) 358 (M+H+).

Workup

customthe white solid was collected
washwashing with water (10 ml) and diethyl ether (10 ml)
customThe solid was dried

Sources & evidence

ORD record: ord-257fe120775449f3b8e7d4da50f6e2c8
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479506B1

Reaction notes

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