Methyl iodide → HCID 9909686, compound

HRID 1958284Notes

Reaction equation

HRID 1958284 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([OH:30])[CH2:16][N:17]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:23]3[C:18]2=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CI.[CH2:35](Cl)Cl.CO>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([O:30][CH3:35])[CH2:16][N:17]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[C:24]3[C:29]2=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2841332HCID 2841332, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 9909686HCID 9909686, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 7 (0.200 g, 0.50 mmol) in 5 mL of THF are added NaH (0.068 g, 1.56 mmol) and methyl iodide (125 μL, 2.0 mmol). After 2 hr of stirring at rt the reaction is judged to be complete by tlc monitoring (SiO2, DCM:MeOH (100:3)) and is quenched with a saturated aqueous solution of Na2CO3 (5 mL). Extraction with DCM, drying over MgSO4, concentration in vacuo, flash chromatography on a 2.5×12 cm2 column of silica gel using DCM:MeOH (95:5) as eluting solvent and removal of the solvent in vacuo gives the title compound as an oil. Slow addition of HCl (4 eq, 1M in Et2O) into a solution of the above compound in EtOH (2 mL) gives the hydrochloride salt of the title compound (0.39 g) as white crystals in a 60% yield. M.p.: 272° C.

Workup

  1. customis quenched with a saturated aqueous solution of Na2CO3 (5 mL)
  2. extractionExtraction with DCM
  3. dry with materialdrying over MgSO4, concentration in vacuo, flash chromatography on a 2.5×12 cm2 column of silica gel
  4. washas eluting
  5. customsolvent and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-734986ae7b084797a685e3c18d238e54
Source dataset
uspto-grants-2013_04
Patent number
US08410110B2

Reaction notes

Loading…