Methyl iodide → HCID 22032977, compound

HRID 1791509Notes

Reaction equation

HRID 1791509 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[C:12]3[CH2:18][C:19]#[N:20])=[CH:5][CH:4]=1.[H-].[Na+].I[CH3:26]>C1COCC1>[CH3:26][N:14]1[C:15]2[C:11](=[CH:10][C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:21])([F:1])[F:22])=[CH:4][CH:5]=3)=[CH:17][CH:16]=2)[C:12]([CH2:18][C:19]#[N:20])=[CH:13]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22032925HCID 22032925, compound

Product 1

HCID 22032977HCID 22032977, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[1-Methyl-5-(4-trifluoromethyl-phenyl)-1H-indol-3-yl]-acetonitrile was prepared from [5-(4-trifluoromethyl-phenyl)-1H-indol-3-yl]-acetonitrile (0.377 g, 1.26 mmol), sodium hydride (0.117 g, 2.93 mmol of a 60% dispersion on mineral oil), iodomethane ( 0.17 mL, 2.8 mmol) and THF (10 mL) according to the procedure described in Step 2 of Example 1. Purification by flash chromatography using 5-15% ethyl acetate in hexane as an eluant afforded the title compound as a yellow semi-solid (0.237 g, 60%), 1HNMR (300 MHz, DMSO-d6): δ 8.0 (s, 1H), 7.9 (d, 2H, J=7.7 Hz), 7.8 (d, 2H, J=7.7 Hz), 7.6 (s, 2H), 7.45 (s, 1H) 4.15 (s, 2H) and 3.8 ppm (s, 3H).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-072604a9467041429ec0d15ea0bffc5c
Source dataset
uspto-grants-2006_07
Patent number
US07074817B2

Reaction notes

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