Methyl iodide → 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-2H-indazole-3-carboxamide

HRID 595705Notes

Reaction equation

[Br:1][C:2]1[C:10]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:9][C:8]2[C:4](=[C:5]([C:23]([NH:25][CH3:26])=[O:24])[N:6]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:7]=2)[CH:3]=1.[C:27]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[C:10]([N:11]([CH3:27])[S:12]([CH3:15])(=[O:13])=[O:14])=[CH:9][C:8]2[C:4](=[C:5]([C:23]([NH:25][CH3:26])=[O:24])[N:6]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[N:7]=2)[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-2H-indazole-3-carboxamide (0.5 g, 1.1 mmol) and K2CO3 (0.5 g, 3.4 mmol) in DMF (10 mL) was added dropwise CH3I (0.8 g, 5.6 mmol) at 0° C. under N2, and then the mixture was stirred at 80° C. for 2 hours. After concentration under vacuum, the residue was suspended in H2O and extracted with DCM. The combined organic layer was washed with H2O, brine, dried over Na2SO4, filtrated and concentrated to give 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-2H-indazole-3-carboxamide (0.48 g, yield: 93%). 1H-NMR (CDCl3, 400 MHz) δ 8.21 (s, 1H), 8.01 (s, 1H), 7.56˜7.60 (m, 2H), 7.21˜7.27 (m, 2H), 6.97 (s, 1H), 3.228 (s, 3H), 3.07 (d, J=4.8 Hz, 3H), 2.77 (s, 3H). MS (M+H)+: 455/457.

Workup

concentrationAfter concentration under vacuum
extractionextracted with DCM
washThe combined organic layer was washed with H2O, brine
dry with materialdried over Na2SO4
filtrationfiltrated
concentrationconcentrated

Sources & evidence

ORD record: ord-44594b247883409db9d9be62545d1b63
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09243002B2

Reaction notes

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