Methyl iodide → HCID 15295122, compound

HRID 726727Notes

Reaction equation

[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH2:6][CH2:7][C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[O:20])[N:10]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:29](=[O:38])[C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=3)[CH:23]=2)[N:9]=1.[H-].[Na+].I[CH3:51]>CN(C=O)C.C(OCC)(=O)C.O>[F:47][C:2]([F:1])([F:46])[C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([C:42]([F:43])([F:44])[F:45])[CH:41]=1)[CH2:6][CH2:7][C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[O:20])[N:10]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N:28]([CH3:51])[C:29](=[O:38])[C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=3)[CH:23]=2)[N:9]=1

Participants

Conditions

Temperature: 25 °C

Procedure

The compound of Example 12 (0.187 g, 0.27 mmol) was dissolved in DMF (10 ml) and sodium hydride (0.016 g, 0.40 mmol) was added followed by iodomethane (0.025 ml, 0.40 mmol). The solution was stirred at 25° C. for 16 hours and diluted with ethyl acetate (30 ml) and water (20 ml). The organic layer was collected and washed with water (3×50 ml), dried (MgSO4) and filtered and the solvent evaporated. The residue was chromatographed on silica eluting with 30% ethyl acetate/hexanes to yield the title compound as a colourless oil. (84%).

Workup

customThe organic layer was collected
washwashed with water (3×50 ml)
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent evaporated
customThe residue was chromatographed on silica eluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-0074ea854db94eee9e85fc56a0ec9dd6
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05710161

Reaction notes

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