Methyl iodide → HCID 68813930, compound

HRID 731027Notes

Reaction equation

HRID 731027 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[C:5]2[CH3:17].[CH3:18]I>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:18])[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[C:5]2[CH3:17]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 582005985-Bromo-3-methyl-2-phenyl-1H-indole

Product 1

HCID 68813930HCID 68813930, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The desired product was prepared using a procedure similar to step 2 of example 3. Thus, 5-bromo-3-methyl-2-phenyl-1H-indole (1.413 g, 4.938 mmol) was reacted with k-t-butoxide (0.582 g, 5.185 mmol) and methyl iodide (0.736 g, 5.185 mmol) in DMF (15 ml) to give the desired product (1.364 g, 4.544 mmol, 92%) as an off-white solid, mp 77.5-80° C. 1H NMR (DMSO-d6) δ 2.17 (s, 3H), 3.58 (s, 3H), 7.27 (dd, J=1.8, 8.6 Hz, 1H), 7.42-7.48 (m, 4H), 7.54 (t, J=8.1 Hz, 2H), 7.71 (d, J=1.8 Hz, 1H); [EI], m/z 299/301 (M)+.

Workup

  1. customThe desired product was prepared

Sources & evidence

ORD record
ord-3ac223bdae6545929521c21bfe745bf9
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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