Potassium Carbonate → 8-Nitrobenzo[f][1,7]naphthyridin-5-amine

HRID 340313Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][C:7](B2OC(C)(C)C(C)(C)O2)=[C:8]([NH:10]C(=O)OC(C)(C)C)[CH:9]=1)([O-:3])=[O:2].Br[C:28]1[C:29]([C:34]#[N:35])=[N:30][CH:31]=[CH:32][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2=[C:28]3[C:29](=[C:34]([NH2:35])[N:10]=[C:8]2[CH:9]=1)[N:30]=[CH:31][CH:32]=[CH:33]3)([O-:3])=[O:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of tert-butyl 5-nitro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (from the previous step) (1.0 eq.) and 3-bromopicolinonitrile (1.0 eq.) in toluene (0.44 M) was mixed with tetrakis(triphenyl-phosphine)palladium (5 mol %) and 2N aqueous potassium carbonate solution (2.0 eq.). The reaction was heated to 100° C. and stirred overnight. After cooling to ambient temperature, the reaction mixture was filtered to collect the precipitate. The precipitate was rinsed with EtOAc to give 8-nitrobenzo[f][1,7]naphthyridin-5-amine as a yellow solid.

Workup

temperatureAfter cooling to ambient temperature
filtrationthe reaction mixture was filtered
customto collect the precipitate
washThe precipitate was rinsed with EtOAc

Sources & evidence

ORD record: ord-da8e1dc0e3564cce94e8fdfd1786527f
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895577B2

Reaction notes

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