Methyl iodide → HCID 58318783, compound

HRID 2401504Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([NH:12][C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)[CH:11]=1)[C:7]#[N:8].[CH3:19]I>C1COCC1.CCOC(C)=O>[F:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N:12]([CH3:19])[C:13]2[CH:18]=[N:17][CH:16]=[N:15][CH:14]=2)[CH:11]=1)[C:7]#[N:8]

Participants

Conditions

Temperature: 0 °C

Procedure

NaH (23 mg, 0.96 mmol, 1.1 eq) was added to a flame-dried round-bottom flask and anhydrous THF (2.1 mL) was added. The slurry was cooled to 0° C. and compound 11 (185 mg, 0.864 mmol, 1.00 eq) was added as a solution in THF (2.1 mL). After stirring at 0° C. for 30 minutes methyl iodide (59.3 μL, 0.958 mmol, 1.10 eq) was added and the reaction was allowed to warm to room temperature while stirring overnight. The reaction was diluted with EtOAc and washed with water (1×). The aqueous layer was back extracted (1×) with EtOAc and the combined organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 163 mg (83%) of the title compound as a tan solid: 1H NMR (400 MHz, CDCl3) δ 8.93 (s, 1H), 8.71 (s, 2H), 7.32-7.27 (m, 2H), 7.19 (dt, J=11.7, 2.3 Hz, 1H), 3.35 (s, 3H); [M+1]+: 229.2.

Workup

additionwas added
temperatureto warm to room temperature
washwashed with water (1×)
extractionThe aqueous layer was back extracted (1×) with EtOAc
washthe combined organics were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by flash chromatography on silica gel

Sources & evidence

ORD record: ord-0619d96ef8fe488fb4bd9e9757f14d7a
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796295B2

Reaction notes

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