2-Bromo-5-fluoropyridine → 2-(4-(5-Fluoropyridin-2-yl)but-3-ynyl)benzo[d]thiazole

HRID 334626Notes

Reaction equation

HRID 334626 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[CH2:9]([C:13]1[S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)[CH2:10][C:11]#[CH:12]>>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]#[C:11][CH2:10][CH2:9][C:13]2[S:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 27831712-Bromo-5-fluoropyridineHCID 570536282-(But-3-yn-1-yl)-1,3-benzothiazole

Product 1

HCID 115001412-(4-(5-Fluoropyridin-2-yl)but-3-ynyl)benzo[d]thiazoleYield 47.5%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-5-fluoro-pyridine (103 mg, 0.59 mmol) and 2-but-3-ynyl-benzo[d]thiazole (110 mg, 0.59 mmol, Example 35(A)). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 78 mg (0.28 mmol, 47%) of 2-(4-(5-fluoropyridin-2-yl)but-3-ynyl)benzo[d]thiazole as a white solid.

Workup

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

Sources & evidence

ORD record
ord-9f5f724f6e2143f39aa07c3f3f65127c
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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