4-Bromo-1,2-dimethyl-1H-imidazole → 4-chloro-2-(4-(1,2-dimethyl-1H-imidazol-4-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole

HRID 334701Notes

Reaction equation

HRID 334701 reaction equation
Br[C:2]1[N:3]=[C:4]([CH3:8])[N:5]([CH3:7])[CH:6]=1.[CH2:9]([N:13]1[N:17]=[C:16]2[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:15]2=[N:14]1)[CH2:10][C:11]#[CH:12]>>[Cl:22][C:21]1[C:15]2[C:16](=[N:17][N:13]([CH2:9][CH2:10][C:11]#[C:12][C:2]3[N:3]=[C:4]([CH3:8])[N:5]([CH3:7])[CH:6]=3)[N:14]=2)[CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 72048754-Bromo-1,2-dimethyl-1H-imidazoleHCID 860868812-but-3-ynyl-4-chloro-2H-benzo[d][1,2,3]triazole

Product 1

HCID 665981084-chloro-2-(4-(1,2-dimethyl-1H-imidazol-4-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazoleYield 5,510.2%

Procedure

The title compound was prepared in accordance with the general method of Example 108(C), from 4-bromo-1,2-dimethyl-1H-imidazole (85 mg, 0.49 mmol) and 2-but-3-ynyl-4-chloro-2H-benzo[d][1,2,3]triazole (100 mg, 0.49 mmol, Example 146(B)). Microwave conditions: 100° C. for 15 min. The crude residue was purified by C18 flash chromatography to yield 8.0 mg (27 mmol, 5%) of 4-chloro-2-(4-(1,2-dimethyl-1H-imidazol-4-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole as a brown semi-solid.

Workup

  1. customThe crude residue was purified by C18 flash chromatography

Sources & evidence

ORD record
ord-0951ff403e844fe8861b2c0dc8985551
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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