Triethylamine → 5,11-Dihydro-11-ethyl-5-methyl-8-phenylethynyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 724946Notes

Reaction equation

HRID 724946 reaction equation
Br[C:2]1[CH:22]=[N:21][C:5]2[N:6]([CH2:19][CH3:20])[C:7]3[N:16]=[CH:15][C:14](C)=[C:13](C)[C:8]=3[N:9]([CH3:12])[C:10](=[O:11])[C:4]=2[CH:3]=1.[C:23]1([C:29]#[CH:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH2:19]([N:6]1[C:5]2[N:21]=[CH:22][C:2]([C:30]#[C:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:3][C:4]=2[C:10](=[O:11])[N:9]([CH3:12])[C:8]2[CH:13]=[CH:14][CH:15]=[N:16][C:7]1=2)[CH3:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 197111358-bromo-5,11-dihydro-3,4-dimethyl-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Product 1

HCID 105701215,11-Dihydro-11-ethyl-5-methyl-8-phenylethynyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneYield 120.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 8-bromo-5,11-dihydro-3,4-dimethyl-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.05 g, 0.14 mmol), phenylacetylene (0.03 g, 0.28 mmol), and triethylamine (3.5 mL) in 1.5 mL of acetonitrile was added tetrakis(triphenylphosphine)palladium(0) (10 mg) and copper(I) iodide (5 mg). The resultant mixture was heated at reflux for 2 hours. The solvent was removed at reduced pressure, and the residue was purified by preparative thin layer chromatography, eluting with ethyl acetate/hexanes. The product was recrystallized from ethyl acetate/petroleum ether to provide 60 mg of the title compound, m.p. 228°-229° C.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was removed at reduced pressure
  3. customthe residue was purified by preparative thin layer chromatography
  4. washeluting with ethyl acetate/hexanes
  5. customThe product was recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-da83375588fa41caa341f9ae9ccce6e6
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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