3-(2-Bromoacetyl)benzonitrile → HCID 86646641, compound

HRID 2039789Notes

Reaction equation

HRID 2039789 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=[O:21])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]=3[CH3:20])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Br:22][CH2:23][C:24]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[C:29]#[N:30])=[O:25]>CC(C)=O>[Br-:22].[C:1]12([CH2:11][NH:12][C:13]([C:14]3[C:15]([CH3:20])=[N+:16]([CH2:23][C:24]([C:26]4[CH:33]=[CH:32][CH:31]=[C:28]([C:29]#[N:30])[CH:27]=4)=[O:25])[CH:17]=[CH:18][CH:19]=3)=[O:21])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

4

Reactant 2

HCID 27358673-(2-Bromoacetyl)benzonitrileHCID 59539003HCID 59539003, compound

Product 1

HCID 86646641HCID 86646641, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of N-(adamantan-1-ylmethyl)-2-methylnicotinamide (300 mg, 1.05 mmol) and 3-(bromoacetyl)benzonitrile (235 mg, 1.05 mmol) in 10 mL of acetone is stirred at reflux for 2.5 days. After cooling to rt, most of the acetone is evaporated, and the remaining mixture is filtered. The collected solid is dried in vacuo to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.93 (1H, m), 8.86 (1H, bs), 8.62 (1H, d), 8.58 (1H, s), 8.33 (1H, d), 8.26 (1H, d), 8.14 (1H, t), 7.87 (1H, t), 6.60 (2H, s), 3.01 (2H, d), 2.67 (3H, s), 1.94 (3H, s), 1.63 (6H, m), 1.51 (6H, s).

Workup

  1. temperatureat reflux for 2.5 days
  2. customis evaporated
  3. filtrationthe remaining mixture is filtered
  4. customThe collected solid is dried in vacuo

Sources & evidence

ORD record
ord-4dd7594cb1134ccea652d64340506660
Source dataset
uspto-grants-2013_11
Patent number
US08580812B2

Reaction notes

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