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

HRID 334791Notes

Reaction equation

HRID 334791 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.[CH2:8]([N:12]1[N:16]=[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]2=[N:13]1)[CH2:9][C:10]#[CH:11]>>[CH3:7][C:5]1[N:6]=[C:2]([C:11]#[C:10][CH2:9][CH2:8][N:12]2[N:13]=[C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]3=[N:16]2)[S:3][CH:4]=1

Participants

3

Reactant 2

HCID 5515412-Bromo-4-methyl-1,3-thiazoleHCID 576917912-but-3-ynyl-2H-benzo[d][1,2,3]triazole

Product 1

HCID 665980142-(4-(4-methylthiazol-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazoleYield 27%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-4-methylthiazole (100 mg, 0.56 mmol) and 2-(but-3-ynyl)-2H-benzo[d][1,2,3]triazole (96 mg, 0.56 mmol, Example 109(D)). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 40 mg (0.15 mmol, 27%) of 2-(4-(4-methylthiazol-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole as a white solid (M.P.=78-80° C.).

Workup

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

Sources & evidence

ORD record
ord-386eab59b0bf47da952ef1fce456b579
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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