Methyl iodide → HCID 67090942, compound

HRID 2075706Notes

Reaction equation

[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([S:12][C:13]3[CH:14]=[C:15]([C:19]4([C:25]#[N:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:16]=[CH:17][CH:18]=3)[CH:9]=2)[N:4]2[C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:28][N:29]=[C:3]12.[CH3:36]C(C)([O-])C.[K+].IC>C1COCC1.CCOC(C)=O.O>[CH3:36][N:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([S:12][C:13]3[CH:14]=[C:15]([C:19]4([C:25]#[N:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:16]=[CH:17][CH:18]=3)[CH:9]=2)[N:4]2[C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:28][N:29]=[C:3]2[C:2]1=[O:1]

Participants

Conditions

Temperature: 0 °C

Procedure

7c (58 mg, 0.12 mmol) was dissolved in THF (1.2 μL) and cooled to 0° C. Potassium tert-butoxide (18 mg, 0.16 mmol) was added, followed by iodomethane (0.01 mL, 0.18 mmol), and the reaction was warmed to room temperature and stirred overnight. The reaction was diluted with EtOAc and water, and the aqueous layer was extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (20-100% EtOAc, followed by 10% MeOH in EtOAc) to give the desired product, 7d.

Workup

temperaturethe reaction was warmed to room temperature
extractionthe aqueous layer was extracted with EtOAc
washThe combined organics were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography (20-100% EtOAc, followed by 10% MeOH in EtOAc)

Sources & evidence

ORD record: ord-f116bae61bec48539e8dffc58cc2082b
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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