Sodium hydride → 4-((4-iodo-1H-pyrazol-1-yl)methyl)pyridin-2(1H)-one

HRID 595233Notes

Reaction equation

[H-].[Na+].[I:3][C:4]1[CH:5]=[N:6][NH:7][CH:8]=1.Br[CH2:10][C:11]1[CH:16]=[CH:15][NH:14][C:13](=[O:17])[CH:12]=1>C1COCC1>[I:3][C:4]1[CH:5]=[N:6][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][NH:14][C:13](=[O:17])[CH:12]=2)[CH:8]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Sodium hydride (19 mg, 0.48 mmol, 60 wt %) was added to a solution of 4-iodo-1H-pyrazole (47 mg, 0.24 mmol) in THF (2 mL) at 0° C. After 30 minutes, 4-(bromomethyl)pyridin-2(1H)-one (30 mg, 0.16 mmol) was added. The mixture was stirred at 25° C. for 12 hours. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/MeOH) to afford 4-((4-iodo-1H-pyrazol-1-yl)methyl)pyridin-2(1H)-one. MS ESI calc'd. for C9H9IN3O [M+H]+ 302. found 302. 1H NMR (400 MHz, DMSO-d6) δ 11.54 (s, 1H), 8.05 (s, 1H), 7.61 (s, 1H), 7.32 (d, J=6.8 Hz, 1H), 5.93-5.90 (m, 2H), 5.19 (s, 2H).

Workup

dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (EtOAc/MeOH)

Sources & evidence

ORD record: ord-992745fd4d7d445e90413a99976077be
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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