2-Bromobenzyl cyanide → 2-(2-Bromophenyl)-3,3-dipyridin-3-ylpropanenitrile

HRID 1686079Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].Cl[CH:12]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH:12]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:9]#[N:10]

Participants

Conditions

Temperature: 0 °C

Procedure

To the solution of (2-bromophenyl)acetonitrile (1.05 g, 5.38 mmol) in THF (20 mL) at 0° C. was added L DS (5.9 mL, 1.0 M). The mixture was stirred at 0° C. for 30 min followed by the addition of a solution of 3-[chloro(pyridin-3-yl)methyl]pyridine (1.1 g, 5.38 mmol) in THF (5 mL). The mixture was stirred at 0° C. for 2 h and the reaction was quenched with water (20 mL) and extracted with CH2Cl2. The combined organic layer was dried, filtered, and concentrated to give a solid. The solid was purified by silica gel chromatography (3% MeOH in CH2Cl2) to give 2-(2-bromophenyl)-3,3-dipyridin-3-ylpropanenitrile. 1H-NMR (500 MHz, CDCl3) δ 8.57-8.54 (m, 3H), 8.26 (d, 1H, J=2.0, 2.0), 7.76 (d, 1H, J=7.8), 7.73 (d, 1H, J=8.1), 7.59 (d, 1H, J=7.8), 7.34-7.11 (m, 5H), 5.12 (d, 1H, J=6.1), 4.58 (d, 1H, J=6.1). LRMS m/z (M+H) Calcd: 364.3, found: 363.9.

Workup

stirringThe mixture was stirred at 0° C. for 2 h
customthe reaction was quenched with water (20 mL)
extractionextracted with CH2Cl2
customThe combined organic layer was dried
filtrationfiltered
concentrationconcentrated
customto give a solid
customThe solid was purified by silica gel chromatography (3% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-6209679c2b7a4a18918f9ada05889b87
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148535B2

Reaction notes

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