Potassium Carbonate → HCID 90333092, compound

HRID 595661Notes

Reaction equation

[Br:1][C:2]1[C:3]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:4][C:5]2[O:9][C:8](I)=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1.[CH3:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([OH:29])[CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:4][C:5]2[O:9][C:8]([N:26]3[CH:27]=[CH:28][C:23]([CH3:22])=[CH:24][C:25]3=[O:29])=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (500 mg, 1.03 mmol), 4-methylpyridin-2-ol (168 mg, 1.54 mmol) and K2CO3 (283 mg, 2.05 mmol) in DMF (5 mL) was stirred at 80° C. for 10 hours and concentrated in vacuo to remove DMF. The reaction mixture was extracted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (PE:EtOAc=1:1) to give the product of 5-bromo-N-methyl-2-(4-methyl-2-oxopyridin-1 (2H)-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (400 mg, yield: 83%). 1H-NMR (CDCl3, 400 MHz) δ 8.32 (s, 1H), 7.85 (s, 1H), 7.67 (s, 1H), 7.22 (d, J=7.2 Hz, 1H), 6.52 (s, 1H), 6.28 (d, J=1.6 Hz, 1H), 3.32 (s, 3H), 3.06 (s, 3H), 2.89 (d, J=4.8 Hz, 3H), 2.31 (s, 3H). MS (M+H)+: 468/470.

Workup

concentrationconcentrated in vacuo
customto remove DMF
extractionThe reaction mixture was extracted with EtOAc
washwashed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (PE:EtOAc=1:1)

Sources & evidence

ORD record: ord-c140e2d702424fe896a42020c019e8e5
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09243002B2

Reaction notes

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