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

HRID 334569Notes

Reaction equation

HRID 334569 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[CH2:9]([C:13]1[O: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[O: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 860869072-(But-3-ynyl)benzo[d]oxazole

Product 1

HCID 116876022-(4-(5-Fluoropyridin-2-yl)but-3-ynyl)benzo[d]oxazoleYield 5%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-5-fluoropyridine (200 mg, 1.14 mol) and 2-(but-3-ynyl)benzo[d]oxazole (195 mg, 1.14 mmol, Example 8(A)). The crude residue was purified by flash chromatography (DCM/MeOH 99:1) and SCX column (DCM/MeOH 100:0 to 94:6, DCM/MeOH/NH4OH 94:5:1 to 90:8:2) to yield 15 mg (56 μmol, 5%) of 2-(4-(5-fluoropyridin-2-yl)but-3-ynyl)benzo[d]oxazole as a white solid.

Workup

  1. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1) and SCX column (DCM/MeOH 100:0 to 94:6, DCM/MeOH/NH4OH 94:5:1 to 90:8:2)

Sources & evidence

ORD record
ord-a18356375b934d7c816b384df8c0058f
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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