Methyl iodide → 1H-Indole-7-carboxylic acid (4-tert-butyl-2-methoxy-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide

HRID 855452Notes

Reaction equation

[C:1]([C:5]1[CH:32]=[CH:31][C:8]([CH2:9][N:10]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:21]=2[NH:20][CH:19]=[CH:18]3)=[O:12])=[C:7]([OH:33])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CI.[C:36](=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:5]1[CH:32]=[CH:31][C:8]([CH2:9][N:10]([CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:21]=2[NH:20][CH:19]=[CH:18]3)=[O:12])=[C:7]([O:33][CH3:36])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

133 mg (0.3 mmol) of 1H-indole-7-carboxylic acid (4-tert-butyl-2-hydroxy-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide, 64 mg (0.45 mmol) of methyl iodide and 83 mg (0.6 mmol) of potassium carbonate were heated in 3 ml acetonitrile for 2 h to 60° C. Additional 32 mg (0.22 mmol) of methyl iodide were added and the reaction mixture was heated to 60° C. over night. The reaction mixture was filtered and the solvent was evaporated. The residue was purified by column chromatography (20 g silica gel; DCM/diethyl ether 10:1) to yield 54 mg (39%) product as a colorless gum. MS (ISP) 459.6 (M+H)+.

Workup

filtrationThe reaction mixture was filtered
customthe solvent was evaporated
customThe residue was purified by column chromatography (20 g silica gel; DCM/diethyl ether 10:1)

Sources & evidence

ORD record: ord-3454d691c670410381a239cd57a3e4e8
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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