Methyl iodide → 2-[3-(6-Chloro-2-methyl-1-pyridin-3-yl-1H-indol-3-ylsulfanyl)-phenyl]-propionic acid ethyl ester

HRID 1466918Notes

Reaction equation

[CH:1]([N-]C(C)C)(C)C.[Li+].[CH2:9]([O:11][C:12](=[O:38])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([S:20][C:21]2[C:29]3[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=3)[N:23]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[C:22]=2[CH3:37])[CH:15]=1)[CH3:10].IC>C1COCC1>[CH2:9]([O:11][C:12](=[O:38])[CH:13]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([S:20][C:21]2[C:29]3[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=3)[N:23]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[C:22]=2[CH3:37])[CH:15]=1)[CH3:1])[CH3:10]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of lithium diisopropylamide (10.7 mmol) in THF (10 mL), freshly prepared at −78° C., was added to a solution of ([3-(6-Chloro-2-methyl-1-pyridin-3-yl-1H-indol-3-ylsulfanyl)-phenyl]-acetic acid ethyl ester (0.256 g, 0.586 mmol) in THF (5 mL) at −78° C. The reaction was stirred at −78° C. for 2 hours then iodomethane (0.044 mL, 0.71 mmol) was added and the reaction was allowed to warm to 0° C. After stirring at 0° C. for 30 minutes the reaction was submitted to standard aqueous workup then purified by silica gel chromatography (0-30% EtOAc in hexanes) to yield the title compound.

Workup

temperatureto warm to 0° C
stirringAfter stirring at 0° C. for 30 minutes the reaction
customthen purified by silica gel chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record: ord-50bbd27ad22345bab8e42435a4b19bc7
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000025B2

Reaction notes

Loading…