3-Bromo-1-methyl-1H-pyrazole → 4-chloro-2-(4-(1-methyl-1H-pyrazol-3-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole

HRID 334680Notes

Reaction equation

HRID 334680 reaction equation
Br[C:2]1[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=1.[CH2:8]([N:12]1[N:16]=[C:15]2[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:14]2=[N:13]1)[CH2:9][C:10]#[CH:11]>>[Cl:21][C:20]1[C:14]2[C:15](=[N:16][N:12]([CH2:8][CH2:9][C:10]#[C:11][C:2]3[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=3)[N:13]=2)[CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 149486373-Bromo-1-methyl-1H-pyrazoleHCID 860868812-but-3-ynyl-4-chloro-2H-benzo[d][1,2,3]triazole

Product 1

HCID 665983434-chloro-2-(4-(1-methyl-1H-pyrazol-3-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazoleYield 10%

Procedure

The title compound was prepared in accordance with the general method of Example 108(C), from 3-bromo-1-methyl-1H-pyrazole (70 mg, 0.43 mmol) and 2-but-3-ynyl-4-chloro-2H-benzo[d][1,2,3]triazole (89 mg, 0.43 mmol, Example 146(B)). Microwave conditions: The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3) to yield 12 mg (42 μmol, 10%) of 4-chloro-2-(4-(1-methyl-1H-pyrazol-3-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole as a brown semi-solid.

Workup

  1. customMicrowave conditions: The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3)

Sources & evidence

ORD record
ord-90a304be7c7d4e038f48dd2e7ce66da8
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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