Methyl iodide → 3-Benzyl-5-bromo-1,2-dimethyl-1H-indole

HRID 731060Notes

Reaction equation

HRID 731060 reaction equation
[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:17])[CH:15]=2)[NH:10][C:9]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19]I>CN(C=O)C>[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:17])[CH:15]=2)[N:10]([CH3:19])[C:9]=1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 688163193-Benzyl-5-bromo-2-methyl-1H-indole

Product 1

HCID 688139383-Benzyl-5-bromo-1,2-dimethyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The desired product was prepared using a procedure similar to step 2 of example 3. Thus, 3-benzyl-5-bromo-2-methyl-1H-indole (1.530 g, 5.097 mmol) was reacted with k-t-butoxide (0.601 g, 5.352 mmol) and methyl iodide (0.760 g, 5.352 mmol) in DMF (15 ml) to give the product (1.453 g, 4.624 mmol, 91%) as a yellow solid, mp 104-106° C. 1H NMR (DMSO-d6) δ 2.39 (s, 3H), 3.65 (s, 3H), 3.99 (s, 2H), 7.10-7.14 (m, 2H), 7.18 (d, J=6.7 Hz, 2H), 7.22 (t, J=7.6 Hz, 2H), 7.34 (d, J=8.6 Hz, 1H), 7.49 (d, J=1.8 Hz, 1H); [ESI(+)], m/z 314/316 (M+H)+.

Sources & evidence

ORD record
ord-3e89469895d241c7b759f2f884476655
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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