Potassium Carbonate → N,N-Dimethyl-4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yl)-benzenesulfonamide

HRID 1029137Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.B(O)(O)[C:18]1[CH:23]=[CH:22][C:21]([S:24]([N:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])=[CH:20][CH:19]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.O.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:28][N:27]([CH3:29])[S:24]([C:21]1[CH:20]=[CH:19][C:18]([C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[C:4]2[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=2[C:6](=[O:12])[NH:7]3)=[CH:23][CH:22]=1)(=[O:25])=[O:26]

Participants

Conditions

Temperature: 100 °C

Procedure

Compound 83 (100 mg, 0.43 mmol), 4-(N,N-dimethylsulfonamidophenyl)boronic acid (198 mg, 0.87 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), S-Phos (18 mg, 0.04 mmol), and K2CO3 (299 mg, 2.17 mmol) were dissolved in dioxane/H2O (2.2 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was diluted with H2O/EtOAc. The resulting precipitate was filtered, washed with H2O/EtOAc, and dried under vacuum to provide 171 (120 mg, 73% yield) as a grey solid. LC-MS (M+H=380, obsd.=380).

Workup

filtrationThe resulting precipitate was filtered
washwashed with H2O/EtOAc
customdried under vacuum

Sources & evidence

ORD record: ord-e3e223b43df645e59acb24c10f8d08d9
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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