Potassium Iodide → Ethyl 9-benzyl-5-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxylate

HRID 567351Notes

Reaction equation

HRID 567351 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]2[C:4]=1[C:5]1[CH:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:7][CH2:8][CH2:9][C:10]=1[NH:11]2.[H-].[Na+].[I-].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Cl-].[NH4+]>CN(C)C=O>[CH2:26]([N:11]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]=2[C:4]2[C:12]1=[C:13]([CH3:16])[CH:14]=[CH:15][C:3]=2[O:2][CH3:1])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22739933Ethyl 5-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxylate

Product 1

HCID 22740886Ethyl 9-benzyl-5-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxylateYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1.58 g of ethyl 5-methoxy-8-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxylate in 5 ml of dimethylformamide was added to 0.24 g of sodium hydride (60% in mineral oil) in 5 ml of dimethylformamide and stirred for 30 minutes at room temperature. Potassium iodide (90 mg) and 0.75 ml of benzyl bromide were then added and the reaction was stirred overnight. The reaction mixture was poured into 75 ml of saturated ammonium chloride solution and then extracted twice with ether. The extracts were washed with water and then with brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel using hexane/ethyl acetate mixtures to afford 1.09 g (53%) of the subtitle compound. ESIMS m/e 378 (M++1) NMR (300 MHz, CDCl3): δ 7.28-7.19 (m, 3H); 6.84 (d, J=7.4, 2H); 6.67 (d, J=7.8, 1H); 6.33 (d, J=7.9, 1H); 5.55 and 5.39 (ABq, J=7.8, 2H); 4.17 (q+m, J=6.9, 3H); 3.80 (s, 3H); 2.64 (dt, J=16.1, 5.3, 1H); 2.48 (dt, J=16.6, 6.9,1H); 2.41 (s, 3H); 2.05 (m, 2H); 1.95 (m, 1H); 1.83 (m, 1H); 1.25 (t, J=7.3, 3H).

Workup

  1. stirringthe reaction was stirred overnight
  2. extractionextracted twice with ether
  3. washThe extracts were washed with water
  4. dry with materialwith brine, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-abab1faab2f941e08d641456b2845111
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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