Methyl iodide → HCID 57563292, compound

HRID 401603Notes

Reaction equation

HRID 401603 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:27])[C:7]([CH2:16][C:17]1[C:25]2[C:20](=[C:21]([Cl:26])[CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)([NH:13][CH:14]=[O:15])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4].[CH3:28]I>CS(C)=O>[CH2:11]([O:10][C:8](=[O:9])[C:7]([CH2:16][C:17]1[C:25]2[C:20](=[C:21]([Cl:26])[CH:22]=[CH:23][CH:24]=2)[N:19]([CH3:28])[CH:18]=1)([NH:13][CH:14]=[O:15])[C:6]([O:5][CH2:3][CH3:4])=[O:27])[CH3:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 643955HCID 643955, compound

Product 1

HCID 57563292HCID 57563292, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of DMSO (5 mL) and KOH (229 mg, 4.1 mmol) was added 2-(7-Chloro-1H-indol-3-ylmethyl)-2-formylamino-malonic acid diethyl ester (500 mg, 1.4 mmol), followed by MeI (0.127 mL, 2 mmol) at 0° C. The reaction mixture was stirred for 4 hr. After the usual workup the product was purified by column chromatography on silica gel using 30% ethyl acetate-hexane to give 2-(7-Chloro-1-methyl-1H-indol-3-ylmethyl)-2-formylamino-malonic acid diethyl ester (402 mg, 77%): mp 83-87° C., 1H NMR (500 MHz, CDCl3): 1.28 (t, J=7.5 Hz, 6H), 3.81 (s, 2H), 4.08 (s, 3H), 4.17-4.31 (m, 4H), 6.71 (s, 1H), 6.93 (dd, J=7.5 and 7.5 Hz, 1H), 7.10 (d, J=7.5 Hz, 1H), 7.35 (d, J=7.5 Hz, 1H), 8.18 (d, J=1.0 Hz, 1H).

Workup

  1. customAfter the usual workup the product was purified by column chromatography on silica gel using 30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-08dfea7029ab4fb182570c735ccb37dd
Source dataset
uspto-grants-2014_06
Patent number
US08741942B2

Reaction notes

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