Sodium Carbonate → HCID 90332539, compound

HRID 595671Notes

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[S:24][CH:25]=[CH:26][N:27]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.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]>[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]([C:25]3[S:24][C:23]([CH3:22])=[N:27][CH:26]=3)=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a degassed solution of compound 5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (600 mg, 1.2 mmol), 2-methylthiazole (244 mg, 2.5 mmol) and Na2CO3 (261 mg, 2.5 mmol) in DMF (6 mL) was added Pd(dppf)Cl2 (50 mg) under N2, and the mixture was stirred at 80° C. for 12 h. After the solvent was removed, the residue was purified by column chromatography (DCM:EtOAc=2:1) to give the product of 5-bromo-N-methyl-6-(N-methylmethylsulfonamido)-2-(2-methylthiazol-5-yl)benzofuran-3-carboxamide (240 mg, yield: 42%). 1H-NMR (CDCl3, 400 MHz) δ 8.36 (s, 1H), 7.98˜8.01 (m, 1H), 7.68 (s, 1H), 6.06 (br s., 1H), 3.33 (s, 3H), 3.10 (s, 3H), 3.08 (d, J=5.2 Hz, 3H), 2.78 (s, 3H). MS (M+H)+: 458/460.

Workup

customAfter the solvent was removed
customthe residue was purified by column chromatography (DCM:EtOAc=2:1)

Sources & evidence

ORD record: ord-acef70eca691491184be56ab4377c2d9
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09243002B2

Reaction notes

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