Methyl iodide → HCID 67019918, compound

HRID 1673218Notes

Reaction equation

HRID 1673218 reaction equation
[Br:1][CH:2]1[C:25]2([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[O:24][C:5]2=[N:6][C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[CH:9]=[C:4]2[C:3]1=[O:31].[Li+].[CH3:33][Si]([N-][Si](C)(C)C)(C)C.C1COCC1.IC>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1([CH3:33])[C:25]2([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[O:24][C:5]2=[N:6][C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[C:8]([C:10]3[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=3)[CH:9]=[C:4]2[C:3]1=[O:31]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 67019928HCID 67019928, compound

Product 1

HCID 67019918HCID 67019918, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the product (0.08 g, 0.15 mmol) from Step A in DMF (1 mL) at −78° C., was added 1 M LiHMDS in THF (0.19 mL, 0.19 mmol) and the reaction was stirred for 10 min. Iodomethane (0.05 mL, 0.77 mmol) was added and the reaction was allowed to come to rt. The reaction was stirred an additional 20 min. The reaction was diluted with EtOAc and washed with brine, dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel gradient eluted with 0-20% EtOAc in hexane.

Workup

  1. customto come to rt
  2. stirringThe reaction was stirred an additional 20 min
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica gel gradient
  8. washeluted with 0-20% EtOAc in hexane

Sources & evidence

ORD record
ord-b43d59eaa9024514837d48e7d25cdfd4
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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