2-Bromo-4,5-dimethylthiazole → 2-(4-(4,5-dimethylthiazol-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole

HRID 334779Notes

Reaction equation

HRID 334779 reaction equation
Br[C:2]1[S:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1.[CH2:9]([N:13]1[N:17]=[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]2=[N:14]1)[CH2:10][C:11]#[CH:12]>>[CH3:7][C:5]1[N:6]=[C:2]([C:12]#[C:11][CH2:10][CH2:9][N:13]2[N:14]=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=[N:17]2)[S:3][C:4]=1[CH3:8]

Participants

3

Reactant 2

HCID 99423662-Bromo-4,5-dimethylthiazoleHCID 576917912-but-3-ynyl-2H-benzo[d][1,2,3]triazole

Product 1

HCID 665980482-(4-(4,5-dimethylthiazol-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazoleYield 17,115.4%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-4,5-dimethylthiazole (100 mg, 0.52 mmol) and 2-(but-3-ynyl)-2H-benzo[d][1,2,3]triazole (89 mg, 0.52 mmol, Example 109(D)). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 25 mg (89 mmol, 17%) of 2-(4-(4,5-dimethylthiazol-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole as a yellow solid (M.P.=96-98° C.).

Workup

  1. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1)

Sources & evidence

ORD record
ord-bac02012b12b412cb95ca4efa051264c
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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