2-Bromopyridine → 2-(4-(5-Phenyloxazol-2-yl)but-1-ynyl)pyridine

HRID 422293Notes

Reaction equation

HRID 422293 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]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:15][N:16]=1)[CH2:9][C:10]#[CH:11]>>[C:17]1([C:14]2[O:13][C:12]([CH2:8][CH2:9][C:10]#[C:11][C:6]3[CH:5]=[CH:4][N:3]=[CH:2][CH:7]=3)=[N:16][CH:15]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1.[C:17]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][CH:15]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 79732-BromopyridineHCID 860869172-(But-3-ynyl)-5-phenyloxazole

Product 2

HCID 116662562-(4-(5-Phenyloxazol-2-yl)but-1-ynyl)pyridineYield 18.8%HCID 866302424-(5-Phenyloxazol-2-yl but-1-ynyl)pyridine

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromopyridine (25 mg, 0.16 mmol) and 2-(but-3-ynyl)-5-phenyloxazole (31 mg, 0.16 mmol). The crude residue was purified by flash chromatography (DCM/MeOH 99:1) and SCX column (DCM/MeOH 95:5, DCM/MeOH/NH4OH 90:5:0.1 to 90:9:1) to yield 4.0 mg (15 μmol, 9%) of 2-(4-(5-phenyloxazol-2-yl)but-1-ynyl)pyridine as a yellow oil.

Workup

  1. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1) and SCX column (DCM/MeOH 95:5, DCM/MeOH/NH4OH 90:5:0.1 to 90:9:1)

Sources & evidence

ORD record
ord-acd8210762094eaf9c66bd8ff627327e
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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