Methyl iodide → HCID 86591646, compound

HRID 2212977Notes

Reaction equation

HRID 2212977 reaction equation
CON(C)[C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[N:13]([CH3:22])[CH:12]=1)=[O:5].[H-].[Na+].IC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[N:13]([CH3:22])[CH:12]=1)=[O:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21226445Aluminium lithium hydrideHCID 86591647HCID 86591647, compound

Product 1

HCID 86591646HCID 86591646, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-45 °C

Procedure

A solution of trans-2-(5-Cyano-1-methyl-1H-indol-3-yl)-cyclopentanecarboxylic acid methoxy-methyl-amide (0.25 g, 0.84 mMol) in anhydrous tetrahydrofuran (15 mL) was treated with sodium hydride (0.067 g, 1.68 mMol). The mixture was stirred for 15 minutes and then treated with iodomethane (0.36 g, 2.52 mMol). After stirring 1.5 hours, the mixture was quenched with water and evaporated. The residue was dissolved in ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a hazy oil. This residue was dissolved in anhydrous tetrahydrofuran (5 mL), cooled to −45° C., and treated with lithium aluminum hydride (0.060 g, 1.57 mMol). The suspension was stirred for 1 hour and then quenched in the usual manner. The resulting mixture was filtered over sand and concentrated in vacuo. Silica gel flash column chromatography (50% hexanes, ethyl acetate) gave the product as a clear oil. 1H-NMR (400 MHz, CDCl3) δ 9.66 (1H, d, J=2.8 Hz), 7.94 (1H, m), 7.44 (1H, m), 7.42 (1H, m), 6.99 (1H, s), 3.76 (3H, s), 3.61 (1H, m), 2.98 (1H, m), 2.22 (1H, m), 2.02 (2H, m), 1.98 (1H, m), 1.87 (2H, m).

Workup

  1. stirringAfter stirring 1.5 hours
  2. customthe mixture was quenched with water
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a hazy oil
  10. stirringThe suspension was stirred for 1 hour
  11. customquenched in the usual manner
  12. filtrationThe resulting mixture was filtered over sand
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f71ff5365014ed6a51081562051b393
Source dataset
uspto-grants-2006_09
Patent number
US07105516B2

Reaction notes

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