4-Bromo-2-methyl-1,3-thiazole → 2-(4-(2-Methylthiazol-4-yl)but-3-ynyl)benzo[d]oxazole

HRID 334545Notes

Reaction equation

HRID 334545 reaction equation
Br[C:2]1[N:3]=[C:4]([CH3:7])[S:5][CH:6]=1.[CH2:8]([C:12]1[O: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][C:4]1[S:5][CH:6]=[C:2]([C:11]#[C:10][CH2:9][CH2:8][C:12]2[O: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 27631864-Bromo-2-methyl-1,3-thiazoleHCID 860869072-(But-3-ynyl)benzo[d]oxazole

Product 1

HCID 115145452-(4-(2-Methylthiazol-4-yl)but-3-ynyl)benzo[d]oxazoleYield 2%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 4-bromo-2-methylthiazole (47 mg, 2.7 mmol) and 2-(but-3-ynyl)benzo[d]oxazole (454 mg, 2.65 mmol, Example 8(A)). The reaction mixture was stirred for one day under reflux. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) and trituration with pentane to yield 14 mg (52 μmol, 2%) of 2-(4-(2-methylthiazol-4-yl)but-3-ynyl)benzo[d]oxazole as a beige solid.

Workup

  1. temperatureunder reflux
  2. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) and trituration with pentane

Sources & evidence

ORD record
ord-90e57f6070714e51b3c2d98c7c4c3735
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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