2-Chloronicotinonitrile → HCID 22285317, compound

HRID 1180235Notes

Reaction equation

HRID 1180235 reaction equation
Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1B1OC(C)(C)C(C)(C)O1>>[F:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 810792-ChloronicotinonitrileHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 22285317HCID 22285317, compound

Procedure

2-Chloronicotinonitrile (0.80 g, 5.8 mmol) was coupled to 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (2 g, 7.49 mmol) using the method in Example 2. Purification by chromatography on silica gel eluting with dichloromethane gave 2-(2-fluoro-5-nitrophenyl)-nicotinonitrile as a yellow solid: δH (360 MHz, CDCl3) 8.97 (1H, dd, J 5, 2), 8.56 (1H, dd, J 6, 3), 8.40-8.45 (1H, m), 8.15 (1H, dd, J 8, 2), 7.55 (1H, dd, J 8, 5), 7.43 (1H, dd, J 9, 9); m/z (ES+) 244 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-3f3c5fc5ebae40a58612221fc2a87306
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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