Water → US10023592, Example 283

HRID 575764Notes

Reaction equation

[F:1][C:2]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])=[CH:7][C:6]=1[C:17]1[CH:22]=[C:21]([C:23]#[C:24][Si](C)(C)C)[C:20](=[O:29])[N:19]([CH3:30])[CH:18]=1.C([O-])([O-])=O.[K+].[K+].O>CCO>[F:1][C:2]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH2:15][CH3:16])(=[O:13])=[O:14])=[CH:7][C:6]=1[C:17]1[CH:22]=[C:21]([C:23]#[CH:24])[C:20](=[O:29])[N:19]([CH3:30])[CH:18]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a mixture of N-[4-(2,4-difluorophenoxy)-3-[1-methyl-6-oxo-5-(2-trimethylsilylethynyl)pyridin-3-yl]phenyl]ethanesulfonamide (100 mg, 0.19 mmol) in EtOH (10 mL) was added K2CO3 (157 mg, 1.14 mmol). The reaction was stirred at 20° C. for 12 h and poured into H2O (30 mL) and extracted with DCM (20 mL×3). The organic phase was washed with brine (20 mL), dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by prep-HPLC to afford the title compound (48 mg, 56%) as an off-white solid. 1H NMR (CDCl3, 400 MHz): δ 7.90 (d, J=2.4 Hz, 1H), 7.69 (d, J=2.4 Hz, 1H), 7.26 (d, J=2.8 Hz, 1H), 7.14-7.11 (m, 1H), 7.01-6.94 (m, 2H), 6.89-6.86 (m, 1H), 6.77 (d, J=8.8 Hz, 1H), 6.55 (s, 1H), 3.67 (s, 3H), 3.34 (s, 1H), 3.14 (q, J=7.2 Hz, 2H), 1.42 (t, J=7.2 Hz, 3H). LCMS (M+H)+=445.

Workup

extractionextracted with DCM (20 mL×3)
washThe organic phase was washed with brine (20 mL)
dry with materialdried over anhydrous MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by prep-HPLC

Sources & evidence

ORD record: ord-80d8de9e10a84f92ba1c631848867f29
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034900B2

Reaction notes

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