1-(3,3-dimethyl-indan-1-yl)-5-vinyl-1H-imidazole → 1-(3,3-dimethyl-indan-1-yl)-5-ethyl-1H-imidazole

HRID 2089518Notes

Reaction equation

HRID 2089518 reaction equation
[CH3:1][C:2]1([CH3:18])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([N:11]2[C:15]([CH:16]=[CH2:17])=[CH:14][N:13]=[CH:12]2)[CH2:3]1>CO.[Pd]>[CH3:1][C:2]1([CH3:18])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([N:11]2[C:15]([CH2:16][CH3:17])=[CH:14][N:13]=[CH:12]2)[CH2:3]1

Participants

4

Reactant 1

HCID 591993201-(3,3-dimethyl-indan-1-yl)-5-vinyl-1H-imidazole

Product 1

HCID 591993541-(3,3-dimethyl-indan-1-yl)-5-ethyl-1H-imidazole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(3,3-dimethyl-indan-1-yl)-5-vinyl-1H-imidazole (210 mg, 0.882 mmol), which can be prepared as described in Example 27, in methanol (10 mL) under a nitrogen atmosphere is added 5 wt % palladium on carbon (˜200 mg, ˜0.09 mmol). The atmosphere of the reaction vessel is evacuated of and backfilled with hydrogen gas (balloon pressure). The reaction is permitted to stir under a hydrogen atmosphere for 2 hours and is then diluted with ethyl acetate and filtered through a pad of Celite®. The reaction mixture is concentrated and the residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 1:19 to 1:4) to provide 1-(3,3-dimethyl-indan-1-yl)-5-ethyl-1H-imidazole; HRMS: (ESI) m/z 241.1716 [(M+H)+; calcd for C16H21N2: 241.1705]; 1H NMR (400 MHz, CDCl3) δ ppm 1.29 (s, 3 H), 1.31 (t, J=7.6 Hz, 3 H), 1.42 (s, 3 H), 2.04 (dd, J=12.9, 8.3 Hz, 1 H), 2.51-2.68 (m, 3 H), 5.59 (t, J=8.0 Hz, 1 H), 6.85 (d, J=1.0 Hz, 1 H), 7.04 (d, J=6.8 Hz, 1 H), 7.21-7.29 (m, 3 H), 7.33-7.38 (m, 1 H); The HCl salt of the title compound can be prepared by dissolution in diethyl ether followed by treatment with an excess of 1N HCl in diethyl ether. The resulting heterogeneous solution is concentrated to furnish the HCl salt of 1-(3,3-dimethyl-indan-1-yl)-5-ethyl-1H-imidazole.

Workup

  1. customThe atmosphere of the reaction vessel is evacuated of and
  2. additionis then diluted with ethyl acetate
  3. filtrationfiltered through a pad of Celite®
  4. concentrationThe reaction mixture is concentrated
  5. customthe residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 1:19 to 1:4)

Sources & evidence

ORD record
ord-cb8ed7043ece42adb1108351abc3c32e
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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