2-Bromopyridine → 2-(4-(Pyridin-2-yl)but-3-ynyl)benzo[d]thiazole

HRID 422280Notes

Reaction equation

HRID 422280 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][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]>>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]#[C:10][CH2:9][CH2:8][C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 570536282-(But-3-yn-1-yl)-1,3-benzothiazole

Product 1

HCID 114999402-(4-(Pyridin-2-yl)but-3-ynyl)benzo[d]thiazoleYield 45%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromopyridine (127 mg, 0.80 mmol) and 2-(but-3-ynyl)benzo[d]thiazole (150 mg, 0.80 mmol). Reaction time: 1 day. The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 96 mg (0.36 mmol, 45%) of 2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]thiazole as an orange solid (M.P.=98.5-99.4° C.).

Workup

  1. customReaction time
  2. custom1 day
  3. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-e6951d28ebfa4a339d5cdca7a5e730dc
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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