Methyl iodide → HCID 68814792, compound

HRID 731095Notes

Reaction equation

HRID 731095 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[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[CH3:22]I>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:22])[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[C:5]2[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 68813934HCID 68813934, compound

Product 1

HCID 68814792HCID 68814792, compound

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-pentyl-2-phenyl-1H-indole (1.711 g, 5.000 mmol) was reacted with k-t-butoxide (0.589 g, 5.250 mmol) and methyl iodide (0.745 g, 5.250 mmol) in DMF (15 ml) to give the product (1.113 g, 3.124 mmol, 62%) as a colorless oil. 1H DMSO-d6) δ 0.76 (t, J=7.0 Hz, 3H), 1.13-1.18 (m, 4H), 1.44-1.50 (m, 2H), 2.58 (t, J=7.6 Hz, 2H), 3.53 (s, 3H), 7.27 (dd, J=2.0, 8.7 Hz, 1H), 7.41-7.44 (m, 3H), 7.48 (t, J=7.5 Hz, 1H), 7.54 (t, J=7.0 Hz, 2H), 7.71 (d, J=1.7 Hz, 1H); [ESI(+)], m/z 356/358 (M+H)+.

Sources & evidence

ORD record
ord-3bc931926caa461d91936a27216d4af5
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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