Methyl iodide → 6-Bromo-9-methyl-2,3,4,9-tetrahydro-1H-carbazole

HRID 731048Notes

Reaction equation

HRID 731048 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]2=1.[CH3:15]I>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[C:10]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 2688776-Bromo-1,2,3,4-tetrahydrocarbazole

Product 1

HCID 127170846-Bromo-9-methyl-2,3,4,9-tetrahydro-1H-carbazoleYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The desired product was prepared using a procedure similar to step 2 of example 3. Thus, 6-bromo-2,3,4,9-tetrahydro-1H-carbazole (1.501 g, 6 mmol) was reacted with k-t-butoxide (0.707 g, 6.3 mmol) and methyl iodide (0.894 g, 6.3 mmol) in DMF (15 ml) to give the desired product (1.443 g, 5.463 mmol, 91%) as an off-white solid, mp 70-73° C. 1H NMR (DMSO-d6) δ 1.73-1.77 (m, 2H), 1.82-1.87 (m, 2H), 2.58 (t, J=6.1 Hz, 2H), 2.70 (t, J=6.1 Hz, 2H), 3.58 (s, 3H), 7.13 (dd, J=1.7, 8.6 Hz, 1H), 7.32 (d, J=8.6 Hz, 1H), 7.55 (d, J=1.5 Hz, 1H); [EI], m/z 263/265 (M)+.

Workup

  1. customThe desired product was prepared

Sources & evidence

ORD record
ord-aa4d78e2c902422f96bcea4c40ec121c
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

Loading…