Ammonia → HCID 19364861, compound

HRID 850804Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:12]3=[C:13]([C:15](=[O:25])[C:16]([CH2:18][C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)=[CH:17][N:11]3[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=3)[CH:14]=1.[NH3:26]>[Cu].[Cu](I)I>[NH2:26][C:2]1[CH:3]=[C:4]2[C:12]3=[C:13]([C:15](=[O:25])[C:16]([CH2:18][C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)=[CH:17][N:11]3[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=3)[CH:14]=1

Participants

Conditions

Temperature: 185 °C

Procedure

2-bromo-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (555 mg) produced in Example 178, copper (20 mg), and copper iodide (10 mg) were suspended in aqueous ammonia (28%, 30 ml) in a pressure-resistant microbomb, and the suspension was heated to 180 to 190° C. in an oil bath and stirred for 8 hours. The reaction mixture was then allowed to cool and brought back to normal pressure, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: ethyl acetate), and the crude purification product was recrystallized from ethanol to obtain the title compound (120 mg; 26%).

Workup

temperatureto cool
extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel flash column chromatography (eluent: ethyl acetate)
customthe crude purification product
customwas recrystallized from ethanol

Sources & evidence

ORD record: ord-ed76b0f8fb3749318b37c4b652ddccc9
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06018046

Reaction notes

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