Methyl iodide → [3-(6-Chloro-1,2-dimethyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

HRID 1466760Notes

Reaction equation

HRID 1466760 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:12][C:13]3[CH:14]=[C:15]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[CH:17][CH:18]=3)=[C:7]([CH3:11])[NH:8]2)=[CH:4][CH:3]=1.I[CH3:24]>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:12][C:13]3[CH:14]=[C:15]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[CH:17][CH:18]=3)=[C:7]([CH3:11])[N:8]2[CH3:24])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 66765068[3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

Product 1

HCID 56840628[3-(6-Chloro-1,2-dimethyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

[3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid (0.062 g, 0.19 mmol) was dissolved in DMF (3 mL) and cooled to −10° C. and then sodium bis(trimethyl)amide solution (0.420 mL, 0.42 mmol, 1.0M solution) was added. The reaction was stirred for 1 hour then iodomethane (13 μL, 0.21 mmol) was added in one portion. Standard aqueous workup and purification by preparatory HPLC provided the title compound.

Workup

  1. customStandard aqueous workup and purification by preparatory HPLC

Sources & evidence

ORD record
ord-43ed5be543dc47f39d5f7eda6815f51d
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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