3-Bromoaniline → HCID 18548976, compound

HRID 276878Notes

Reaction equation

HRID 276878 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[Br:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24]>C(O)C>[Br:20][C:21]1[CH:22]=[C:23]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][N:8]=[C:9]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:18]#[N:19])[CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 18548986HCID 18548986, compound

Product 1

HCID 18548976HCID 18548976, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 626 mg of 4-chloro-6-trimethylsilanylethynyl-[1.7]naphthyridine-3-carbonitrile in 20 mL of absolute ethanol was added 1 mL of 3-bromoaniline. After refluxing the reaction under an inert atmosphere for 18 hours, the reaction mixture was cooled to ambient temperature, concentrated to 5 mL, diluted with ether, and the product filtered and washed with ether. Drying in vacuo yielded 500 mg of 4-(3-bromo-phenylamino)-6-trimethylsilanylethynyl-[1.7]naphthyridine-3-carbonitrile as an off-white solid: melting point 125° C. (sublimed); mass spectrum (m/e): M+H 421.1, 423.2.

Workup

  1. temperatureAfter refluxing
  2. customthe reaction under an inert atmosphere for 18 hours
  3. concentrationconcentrated to 5 mL
  4. additiondiluted with ether
  5. filtrationthe product filtered
  6. washwashed with ether
  7. customDrying in vacuo

Sources & evidence

ORD record
ord-8b622c2e0f564ce69b9f90fca3abb364
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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