Methyl iodide → HCID 58554132, compound

HRID 2410500Notes

Reaction equation

HRID 2410500 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[CH3:17])=[C:8]([CH2:10][OH:11])[CH:9]=1.[CH3:18]I>CN(C=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[CH3:17])=[C:8]([CH2:10][O:11][CH3:18])[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58554152HCID 58554152, compound

Product 1

HCID 58554132HCID 58554132, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of sodium hydride (2.84 g, 119 mmol) in anhydrous DMF (80 mL) was added a solution of [5-Bromo-2-(2-methylpyrrolidin-1-yl)phenyl]methanol (16 g, 59.2 mmol) in DMF (50 mL) drop wise at 0° C. After 30 minutes, methyl iodide (7.3 mL, 119 mmol) was added drop wise at 0° C. The reaction mixture was quenched with a saturated aqueous solution of NH4Cl (20 mL), then diluted with water (200 mL) and extracted with EtOAc (150 ml). The organic layer was dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as a yellow oil (16.5 g, 98%). 1H NMR (CDCl3, 400 MHz) δ 7.55 (1H, s), 7.29 (1H, m), 6.86 (1H, d), 4.45 (2H, s), 3.55 (1H, m), 3.41 (1H, m), 2.82 (1H, m), 2.12-2.51 (1H, m), 1.91 (1H, m) 1.81 (1H, m), 1.58 (1H, m), 0.99 (3H, d).

Workup

  1. customThe reaction mixture was quenched with a saturated aqueous solution of NH4Cl (20 mL)
  2. additiondiluted with water (200 mL)
  3. extractionextracted with EtOAc (150 ml)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-472f338ea3a3409b948502d37098e1d2
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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