2-Bromopyridine → 2-(4-(Pyridin-2-yl)but-3-ynyl)isoquinolin-1(2H)-one

HRID 334710Notes

Reaction equation

HRID 334710 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([N:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22])[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][N:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22]

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 818837422-but-3-ynyl-2H-isoquinolin-1-one

Product 1

HCID 665980982-(4-(Pyridin-2-yl)but-3-ynyl)isoquinolin-1(2H)-oneYield 9,841.3%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromopyridine (100 mg, 0.63 mmol) and 2-but-3-ynyl-2H-isoquinolin-1-one (120 mg, 0.63 mmol). Reaction time: 3 hours. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 17 mg (62 mmol, 10%) of 2-(4-(pyridin-2-yl)but-3-ynyl)isoquinolin-1(2H)-one as a white solid (M.P.=85-90° C.).

Workup

  1. customReaction time
  2. custom3 hours
  3. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1)

Sources & evidence

ORD record
ord-fc0a0268be2847578002168ef9bb52c5
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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