2-Bromopyridine → Quinoline

HRID 422356Notes

Reaction equation

HRID 422356 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)[CH2:9][C:10]#[CH:11]>>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:11]#[C:10][CH2:9][CH2:8][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1.[N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][CH:12]=1

Participants

4

Reactant 2

HCID 79732-BromopyridineHCID 2147067491718-27-3

Product 2

HCID 7047QuinolineHCID 66598130HCID 66598130, compound

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-pyridine (87 mg, 0.55 mmol) and 2-but-3-ynyl-quinoline (100 mg, 0.55 mmol). Reaction time: 120° C. for 15 minutes. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 1:1) to yield 74 mg (0.29 mmol, 52%) of 2-(pyridin-2-yl)but-3-ynyl)quinoline as a yellow oil.

Workup

  1. customReaction time
  2. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 1:1)

Sources & evidence

ORD record
ord-502712c5fcd24383a0bcd9daee9ba8a1
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

Loading…