4-Bromo-2-nitroaniline → 4-(3-Dimethylamino-prop-1-ynyl)-2-nitro-phenylamine

HRID 58158

Reaction equation

HRID 58158 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH3:12][N:13]([CH3:17])[CH2:14][C:15]#[CH:16]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:12][N:13]([CH3:17])[CH2:14][C:15]#[C:16][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 2

HCID 701324-Bromo-2-nitroanilineHCID 81643N,N-Dimethylpropargylamine

Product 1

HCID 1180246144-(3-Dimethylamino-prop-1-ynyl)-2-nitro-phenylamineYield 100.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-bromo-2-nitro-phenylamine (1.08 g, 5 mmol) and dimethyl-prop-2-ynyl-amine (1.0 g, 12 mmol) in TEA (20 mL) was added Pd(PPh3)2Cl2 (0.7 g, 1 mmol) and CuI (360 g, 2 mmol). The solution was stirred at 60° C. under nitrogen for 3 hours. The solution was evaporated with silica gel and purified by flash chromatography on silica to give the title compound (1.1 g, 70% purity). The title compound was taken directly to the next step without further purification. MS (ESI) 221 [M+H]+.

Workup

  1. customThe solution was evaporated with silica gel
  2. custompurified by flash chromatography on silica

Sources & evidence

ORD record
ord-7785647e4fe445b2be9d75300737977f
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Linked notes

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