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

HRID 334637Notes

Reaction equation

HRID 334637 reaction equation
Br[C:2]1[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=1.[CH2:8]([C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1)[CH2:9][C:10]#[CH:11]>>[CH3:7][N:4]1[CH:5]=[CH:6][C:2]([C:11]#[C:10][CH2:9][CH2:8][C:12]2[S:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[N:3]1

Participants

3

Reactant 2

HCID 149486373-Bromo-1-methyl-1H-pyrazoleHCID 570536282-(But-3-yn-1-yl)-1,3-benzothiazole

Product 1

HCID 665982002-(4-(1-methyl-1H-pyrazol-3-yl)but-3-ynyl)benzo[d]thiazoleYield 21%

Procedure

The title compound was prepared in accordance with the general method of Example 108(C), from 3-bromo-1-methyl-1H-pyrazole (100 mg, 0.62 mmol) and 2-but-3-ynyl-benzo[d]thiazole (233 mg, 1.24 mmol, Example 35(A)). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3) to yield 35 mg (0.13 mmol, 21%) of 2-(4-(1-methyl-1H-pyrazol-3-yl)but-3-ynyl)benzo[d]thiazole as a brown semi-solid.

Workup

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

Sources & evidence

ORD record
ord-187ef6449f264e9c88129de9ab86abec
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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