N-methyl-2-pyrrolidone → HCID 178422110, compound

HRID 61833Notes

Reaction equation

Br[C:2]1[C:22]([O:23]C)=[CH:21][C:5]2[C:6]([CH3:20])([CH3:19])[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[C:16](=[O:17])[C:4]=2[CH:3]=1)=[CH:13][CH:12]=[C:11](Cl)[CH:10]=4.[C:25]([Cu])#[N:26].[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+].[CH3:34][N:35]1C(=O)CCC1>O.C(OCC)(=O)C>[OH:23][C:22]1[C:2]([C:25]2[NH:26][N:30]=[N:29][N:28]=2)=[CH:3][C:4]2[C:16](=[O:17])[C:15]3[C:14]4[C:9](=[CH:10][C:11]([C:34]#[N:35])=[CH:12][CH:13]=4)[NH:8][C:7]=3[C:6]([CH3:19])([CH3:20])[C:5]=2[CH:21]=1

Participants

Conditions

Temperature: 210 °C

Procedure

9-Bromo-3-chloro-8-methoxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound S1-4, 150 mg, 0.37 mMol) was dissolved in NMP, added with CuCN (100 mg, 3 eq.), and stirred at 210° C. for 1.5 hr under irradiation with microwave. After cooling, the reaction solution was added with water and ethyl acetate, and the precipitated solid was filtered to remove the solvent. The obtained residues were dissolved in DMF (1 ml), added with sodium azide (100 mg, 8 eq.) and ammonium chloride (5 mg), and then stirred at 120° C. for 24 hr in a sealed tube. After adding water, the insoluble matters were filtered and purified by HPLC to obtain the title compound (6.5 mg).

Workup

temperatureAfter cooling
filtrationthe precipitated solid was filtered
customto remove the solvent
dissolutionThe obtained residues were dissolved in DMF (1 ml)
stirringstirred at 120° C. for 24 hr in a sealed tube
filtrationthe insoluble matters were filtered
custompurified by HPLC

Sources & evidence

ORD record: ord-b3666616d2f7422abef3d9a85f2bf725
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Reaction notes

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