Nitrogen → HCID 59375654, compound

HRID 2193005Notes

Reaction equation

HRID 2193005 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]2[C:6]([NH:15][CH:16]([CH3:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.[C:24]1([C:30]#[CH:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N#N>CCN(CC)CC.O.[Cu]I.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>[C:24]1([C:30]#[C:31][C:2]2[CH:23]=[CH:22][C:5]3[C:6]([NH:15][CH:16]([CH3:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:7][C:8]4[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=4[C:4]=3[CH:3]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 3

HCID 947NitrogenHCID 10821PhenylacetyleneHCID 25097260HCID 25097260, compound

Product 1

HCID 59375654HCID 59375654, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 9-bromo-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one (150 mg, 0.040 mmol) in Et3N (3.0 mL) was added the phenylacetylene (50 mg, 0.05 mmol), CuI (10 mg) and PdCl2(PPh3)2 (10 mg). The mixture was stirred under reflux and N2 atmosphere for 12 h. After cooling to room temperature, the mixture was diluted with water (5 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine (5 mL), dried over magnesium sulfate, filtered, and concentrated to a crude residue that was purified by preparative TLC to afford 9-(phenylethynyl)-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one. 1H-NMR (300 MHz, MeOH): δ 10.03 (s, 1H), 8.26 (d, J=8.3 Hz, 1H), 7.70 (d, J=9.0 Hz, 1H) 7.39 (m, 1H), 6.62 (m, 4H), 3.30 (s, 1H), 1.27 (d, J=6.9 Hz, 2H), 1.03 (s, 9H). LRMS calculated for C26H25N3O [M+H]+, 396; found 396.

Workup

  1. temperatureunder reflux
  2. extractionextracted with ethyl acetate (3×5 mL)
  3. washThe combined organic layers were washed with brine (5 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a crude residue that
  7. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-89a31d2b590541689be5aa4948f5a500
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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