Methyl iodide → HCID 24885629, compound

HRID 750923Notes

Reaction equation

HRID 750923 reaction equation
[C:1]([CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:20][C@H:19]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:18][C:17]3=[O:26])=[CH:12][C:11]=2[F:27])[CH2:6][CH2:5]1)#[N:2].[CH2:28]([Li])CCC.CI.O.C(OCC)(=O)C>O1CCCC1>[C:1]([CH:3]=[C:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:20][C@H:19]([CH2:21][N:22]([CH3:28])[C:23](=[O:25])[CH3:24])[O:18][C:17]3=[O:26])=[CH:12][C:11]=2[F:27])[CH2:8][CH2:9]1)#[N:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 9885799HCID 9885799, compoundHCID 22728543Water ethylacetateHCID 178418339Butyllithium

Product 1

HCID 24885629HCID 24885629, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Example 9 (1 mmol) was treated with n-butyl lithium (1.6 M in hexane, 1.6 mmol), methyl iodide (2 mmol) in 10 ml tetrahydrofuran at −78° C. temperature. The reaction mixture was with ethyl acetate water mixture. The organic layer was evaporated to give a crude compound, which was chromatographed on a silica gel to give the titled compound in 44% yield.

Workup

  1. customThe organic layer was evaporated
  2. customto give a crude compound, which
  3. customwas chromatographed on a silica gel

Sources & evidence

ORD record
ord-c48c5c1d8707413a82b5796456296f78
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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