Methyl iodide → 2-(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-4-methoxy-but-2-enenitrile

HRID 38345Notes

Reaction equation

[CH:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:14])=[CH:9][N:10]2[CH3:13])=[CH:6][C:5]=1[O:15][CH2:16][C:17]#[N:18])([CH3:3])[CH3:2].[H-].[Na+].CI>>[CH:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:14])=[CH:9][N:10]2[CH3:13])=[CH:6][C:5]=1[O:15][C:16](=[CH:4][CH2:5][O:15][CH3:16])[C:17]#[N:18])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 59598566(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-acetonitrile

Product 1

HCID 670534062-(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-4-methoxy-but-2-enenitrile

Procedure

2-(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-4-methoxy-but-2-enenitrile was prepared from (6-isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-acetonitrile by treatment with sodium hydride and methyl iodide using the procedure of step 6 of Example 2 above.

Sources & evidence

ORD record: ord-8c9935c58af94744a10e4d14bd664ec7
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524725B2

Reaction notes

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