Methyl iodide → HCID 68814415, compound

HRID 731081Notes

Reaction equation

HRID 731081 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:17])=[C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:6]2.[CH3:18]I>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:17])=[C:5]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[N:6]2[CH3:18]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 68814161HCID 68814161, compound

Product 1

HCID 68814415HCID 68814415, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The desired product was prepared using a procedure similar to step 2 of example 3. Thus, 4-bromo-3-methyl-2-phenyl-1H-indole (1.574 g, 5.5 mmol) was reacted with k-t-butoxide (0.648 g, 5.775 mmol) and methyl iodide (0.820 g, 5.775 mmol) in DMF (15 ml) to give the product (1.188 g, 3.957 mmol, 72%) as a colorless oil. 1H DMSO-d6) δ 2.39 (s, 3H), 3.55 (s, 3H), 7.05 (t, J=7.8 Hz, 1H), 7.23 (dd, J=0.8, 7.6 Hz, 1H), 7.42-7.45 (m, 2H), 7.47-7.51 (m, 2H), 7.55 (t, J=6.9 Hz, 2H); [ESI(+)], m/z 300/302 (M+H)+.

Sources & evidence

ORD record
ord-d035737394c64f7a800ffd9869797a35
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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