Potassium Phosphate, Tribasic → N-[3-(2,6-dimethyl-1-oxoisoquinolin-4-yl) phenyl]ethanesulfonamide

HRID 518298Notes

Reaction equation

HRID 518298 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[C:5](=[O:13])[N:4]([CH3:14])[CH:3]=1.[CH2:15]([S:17]([NH:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)(=[O:19])=[O:18])[CH3:16].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:14][N:4]1[CH:3]=[C:2]([C:25]2[CH:26]=[C:21]([NH:20][S:17]([CH2:15][CH3:16])(=[O:18])=[O:19])[CH:22]=[CH:23][CH:24]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[C:5]1=[O:13]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 467388243-(Ethylsulfonamido)phenylboronic acidHCID 1180219484-Bromo-2,6-dimethylisoquinolin-1-one

Product 1

HCID 118022154N-[3-(2,6-dimethyl-1-oxoisoquinolin-4-yl) phenyl]ethanesulfonamideYield 56.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

4-Bromo-2,6-dimethylisoquinolin-1-one (75.0 mg, 0.30 mmol), [3-(ethylsulfonylamino)phenyl]boronic acid (82.0 mg, 0.36 mmol), Pd(dppf)Cl2 (22 mg, 0.03 mmol) and aqueous 1M K3PO4 (0.75 mL) in dioxane (4 mL) were reacted in a manner similar to Example 72, step 3. Isolation, also in a similar manner, gave the title compound (60.0 mg, 48.1%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.42 (d, J=8.4 Hz, 1H), 7.46 (t, J=8.0 Hz, 1H), 7.34 (d, J=8.0 Hz, 1H), 7.29-7.27 (m, 2H), 7.24 (d, J=8.0 Hz, 1H), 7.03 (s, 1H), 6.68 (s, 1H), 3.65 (s, 3H), 3.21 (q, J=7.2 Hz, 2H), 2.42 (s, 3H), 1.43 (t, J=7.2 Hz, 3H). LCMS: 357.0 (M+H)+

Sources & evidence

ORD record
ord-6eb4c5c705144d83a55cfb4607d6256d
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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