Methyl iodide → HCID 57941301, compound

HRID 1437449Notes

Reaction equation

HRID 1437449 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[N:23]2[N:27]=[C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]3=[N:24]2)=[CH:7][CH:6]=1.[CH3:33][Si]([N-][Si](C)(C)C)(C)C.[K+].CI>C1COCC1>[N:27]1[N:23]([C:17]2[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=2[O:15][CH2:14][CH2:13][CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]([CH:4]([CH3:33])[C:3]([OH:2])=[O:32])=[CH:10][CH:9]=2)[N:24]=[C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 11612152HCID 11612152, compound

Product 1

HCID 57941301HCID 57941301, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Compound 490 (0.45 g, 1 mmol) in THF (15 mL) was added KHMDS (3 mL, 1.5 mmol) at −78° C. under N2. The mixture was stirred at −78° for 0.5 hr and MeI (0.56g, 4 mmol) was added. The mixture was stirred at −78° for 2 hrs and was quenched with saturated aqueous NH4Cl, diluted with EtOAc organic layer was dried over NaSO4, evaporated and the residue was purified by flash chromatography on silica gel to afford 0.36g desired product.

Workup

  1. stirringThe mixture was stirred at −78° for 2 hrs
  2. customwas quenched with saturated aqueous NH4Cl
  3. additiondiluted with EtOAc organic layer
  4. dry with materialwas dried over NaSO4
  5. customevaporated
  6. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f94a0bdd317e4737b1b41e6ed474b7ff
Source dataset
uspto-grants-2009_11
Patent number
US07622491B2

Reaction notes

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