2-Bromopyridine → 7-Chloro-5-fluoro-2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazole

HRID 334576Notes

Reaction equation

HRID 334576 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([C:12]1[O:13][C:14]2[C:20]([Cl:21])=[CH:19][C:18]([F:22])=[CH:17][C:15]=2[N:16]=1)[CH2:9][C:10]#[CH:11]>>[Cl:21][C:20]1[C:14]2[O:13][C:12]([CH2:8][CH2:9][C:10]#[C:11][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=3)=[N:16][C:15]=2[CH:17]=[C:18]([F:22])[CH:19]=1

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 860867442-(But-3-ynyl)-7-chloro-5-fluorobenzo[d]oxazole

Product 1

HCID 665982897-Chloro-5-fluoro-2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazoleYield 59.6%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromopyridine (141 mg, 0.89 mmol) and 2-(but-3-ynyl)-7-chloro-5-fluorobenzo[d]oxazole (200 mg, 0.89 mmol). The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 160 mg (0.53 mmol, 59%) of 7-chloro-5-fluoro-2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazole as an orange solid.

Workup

  1. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-4751f6ccabae4722846823efc0229804
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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