Methyl iodide → HCID 18617700, compound

HRID 1264233Notes

Reaction equation

HRID 1264233 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][NH:14][C:15](=[O:30])[C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:23]=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=4)=[CH:18][CH:17]=3)[CH:10]=2)[NH:5][CH:4]=1)#[N:2].[H-].[Na+].I[CH3:34]>CN(C=O)C>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH2:13][NH:14][C:15](=[O:30])[C:16]3[CH:17]=[CH:18][C:19]([C:22]4[CH:23]=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=4)=[CH:20][CH:21]=3)[CH:10]=2)[N:5]([CH3:34])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18617505HCID 18617505, compound

Product 1

HCID 18617700HCID 18617700, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 0.250 g (0.631 mmol) N-(2-[3-Cyano-indol-5-yl]ethyl)-4-(6-methoxypyrid-3-yl)benzamide (reference example 1p) in 5 mL DMF is added to a cooled (0° C.) solution of 0.0328 g (0.820 mmol) sodium hydride (60% dispersion in mineral oil) in 2 mL DMF. After ten minutes 0.043 mL (0.69 mmol) iodomethane is added, and the cooling bath removed. After 3 hours, the reaction is quenched with water, concentrated, and the resulting residue flash chromatographed (2:2:1 CH2Cl2:EtOAc:hexanes) to provide 0.167 g of the product as a white solid in 65% yield. 1H NMR (CDCl3) δ 3.09 (2H, t, J=7 Hz), 3.80 (2H, m), 3.86 (3H, s), 3.99 (3H, s), 6.17 (1H, m, br), 6.83 (1H, d, J=8 Hz), 7.29 (1H, s), 7.37 (1H, d, J=8 Hz), 7.55-7.58 (3H, m), 7.64 (1H, s), 7.76-7.82 (3 H, m), 8.40 (1H, d, J=2 Hz). MS (ion spray) m/z 411 (M+H)+.

Workup

  1. customthe cooling bath removed
  2. customthe reaction is quenched with water
  3. concentrationconcentrated
  4. customthe resulting residue flash chromatographed (2:2:1 CH2Cl2:EtOAc:hexanes)

Sources & evidence

ORD record
ord-8007352161ec407781a4c19a753abee4
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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