2-Bromopyridine → HCID 66598036, compound

HRID 422325Notes

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]([F:21])=[CH:19][CH:18]=[C:17]([C:22]([F:25])([F:24])[F:23])[C:15]=2[N:16]=1)[CH2:9][C:10]#[CH:11]>>[F: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[C:17]([C:22]([F:25])([F:23])[F:24])=[CH:18][CH:19]=1

Participants

Reactant 2

HCID 79732-Bromopyridine

HCID 86086845HCID 86086845, compound

Product 1

HCID 66598036HCID 66598036, compoundYield 14.2%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromopyridine (49 mg, 0.31 mmol) and 2-(but-3-ynyl)-7-fluoro-4-(trifluoromethyl)-benzo[d]oxazole (80 mg, 0.31 mmol). The crude residue was purified by flash chromatography (DCM/MeOH 98.5:1.5) to yield 15 mg (44 μmol, 14%) of 7-fluoro-4-(trifluoromethyl)-2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazole as an orange solid.

Workup

customThe crude residue was purified by flash chromatography (DCM/MeOH 98.5:1.5)

Sources & evidence

ORD record: ord-5b9d9783485044adb2868752db2b7f34
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101637B2

Reaction notes

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