Methyl iodide → (6-{Methyl-[5-(4-trifluoromethoxy-phenyl)-pent-4-ynoyl]-amino}-indol-1-yl)-acetic acid

HRID 751213Notes

Reaction equation

C([O:3][C:4](=[O:33])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:15][C:16](=[O:32])[CH2:17][CH2:18][C:19]#[C:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)[CH:13]=2)[CH:8]=[CH:7]1)C.[CH3:34]I.[H-].[Na+]>>[CH3:34][N:15]([C:16](=[O:32])[CH2:17][CH2:18][C:19]#[C:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][C:28]([F:30])([F:29])[F:31])=[CH:25][CH:26]=1)[C:12]1[CH:13]=[C:14]2[C:9]([CH:8]=[CH:7][N:6]2[CH2:5][C:4]([OH:3])=[O:33])=[CH:10][CH:11]=1

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 68821712{6-[5-(4-Trifluoromethoxy-phenyl)-pent-4-ynoylamino]-indol-1-yl}-acetic acid ethyl ester

Product 1

HCID 11676633(6-{Methyl-[5-(4-trifluoromethoxy-phenyl)-pent-4-ynoyl]-amino}-indol-1-yl)-acetic acid

Procedure

In analogy to the procedure described in example 8 d], {6-[5-(4-trifluoromethoxy-phenyl)-pent-4-ynoylamino]-indol-1-yl}-acetic acid ethyl ester was reacted with methyl iodide in the presence of sodium hydride to give the title compound as brown liquid.

Workup

customdescribed in example 8 d

Sources & evidence

ORD record: ord-0350212c107947f2aca81eb31eabc478
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405236B2

Reaction notes

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