Methyl iodide → HCID 68815678, compound

HRID 731109Notes

Reaction equation

HRID 731109 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[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24]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]([CH3:24])[C:9]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 68814532HCID 68814532, compound

Product 1

HCID 68815678HCID 68815678, compound

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-phenyl-1H-indole (1.811 g, 5 mmol) was reacted with k-t-butoxide (0.589 g, 5.25 mmol) and methyl iodide (0.745 g, 5.25 mmol) in DMF (20 ml) to give the product (1.537 g, 4.085 mmol, 82%) as a white solid, mp 141-145° C. 1H DMSO-d6) δ 3.56 (s, 3H), 3.93 (s, 2H), 7.02 (d, J=6.8 Hz, 2H), 7.07 (t, J=7.3 Hz, 1H), 7.15 (t, J=7.2 Hz, 2H), 7.23 (dd, J=2.0, 8.7 Hz, 1H), 7.40-7.52 (m, 7H); [ESI(+)], m/z 377/379 (M+H)+.

Sources & evidence

ORD record
ord-243084da644b4c93a158f18180d216d7
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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