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

HRID 422298Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[O:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[CH:10]1>>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:4]#[C:5][CH2:6][CH2:7][C:10]2[O:9][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=2)=[N:3][CH:4]=1

Participants

Reactant 2

HCID 9228Benzoxazole

HCID 27831712-Bromo-5-fluoropyridine

Product 1

HCID 116876022-(4-(5-Fluoropyridin-2-yl)but-3-ynyl)benzo[d]oxazoleYield 9.8%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-5-fluoropyridine (200 mg, 1.14 mmol) 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 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

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

Sources & evidence

ORD record: ord-18a3d354a1e3478c873f1f400931cbed
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101637B2

Reaction notes

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