Aniline → HCID 58167963, compound

HRID 1029078Notes

Reaction equation

Cl[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C[C:59](C)([O-:61])C.[Na+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:18]1([NH:17][C:59]([C:11]2[CH:12]=[C:13]3[C:8](=[N:9][CH:10]=2)[NH:7][C:6](=[O:14])[C:5]2[CH:15]=[CH:16][CH:2]=[CH:3][C:4]3=2)=[O:61])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

9-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), aniline (30 mg, 0.33 mmol), palladium(II) acetate (2 mg, 0.01 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (8 mg, 0.02 mmol), and sodium tert-butoxide (63 mg, 0.65 mmol) were suspended in dioxane (2 mL), and stirred overnight at 100° C. The reaction mixture was added directly to a Biotage column. The crude product was purified via Biotage silica-gel chromatography eluting with a gradient of 0 to 10% MeOH in CH2Cl2 to provide 23 (20 mg, 32% yield) as a tan solid. LC-MS (M+H=288, obsd.=288). 1H NMR (400 MHz, d6-DMSO): δ 11.69 (s, 1H), 8.95 (s, 1H), 8.47 (m, 2H), 8.15 (d, 1H), 7.86 (d, 1H), 7.386 (m, 2H), 7.29 (m, 3H), 7.04 (t, 1H).

Workup

additionThe reaction mixture was added directly to a Biotage column
customThe crude product was purified via Biotage silica-gel chromatography
washeluting with a gradient of 0 to 10% MeOH in CH2Cl2

Sources & evidence

ORD record: ord-6dfe34b73dec41338bc8b487c942e71a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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