Diisopropylethylamine → N-(4-bromo-2-cyanophenyl)pyridine-2-carboxamide

HRID 1786774Notes

Reaction equation

HRID 1786774 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[C:4]#[N:5].C(N(CC)C(C)C)(C)C.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26](Cl)=[O:27]>C1(C)C=CC=CC=1>[Br:10][C:7]1[CH:8]=[CH:9][C:2]([NH:1][C:26]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=2)=[O:27])=[C:3]([C:4]#[N:5])[CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 135034Pyridine-2-carbonyl chlorideHCID 4297402-Amino-5-bromobenzonitrile

Product 1

HCID 57598297N-(4-bromo-2-cyanophenyl)pyridine-2-carboxamideYield 70.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-amino-5-bromobenzonitrile 2-1 (2.8 g, 0.014 moles) in toluene was added (4.95 mL, 0.028 moles) of N,N-diisopropylethylamine, followed by slow addition of (2.74 g, 0.015 moles) picolinoyl chloride. The mixture was stirred until complete by TLC. Reaction was filtered and dried under vacuum to afford 3 grams of 2-2. Analytical LCMS: (CH3CN/H2O/1% TFA, 4 min gradient), 95% pure, M+1 peak m/e 301.

Workup

  1. customReaction
  2. filtrationwas filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-8566c8745d034c9587444a8fc88e7e77
Source dataset
uspto-grants-2009_03
Patent number
US07507836B2

Reaction notes

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