Dimethylformamide → 7-isopropyl-1,2-dimethyl-1H-indole

HRID 226088Notes

Reaction equation

HRID 226088 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([CH3:13])=[CH:9]2)([CH3:3])[CH3:2].[CH3:14]N(C=O)C.[H-].[Na+].IC>CCOCC>[CH:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([CH3:14])[C:10]([CH3:13])=[CH:9]2)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 222505907-isopropyl-2-methyl-1H-indole

Product 1

HCID 688581427-isopropyl-1,2-dimethyl-1H-indoleYield 41%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 7-isopropyl-2-methyl-1H-indole (0.75 g, 4.33 mmol) and DMF (2 mL) is added 60% NaH (0.19 g, 4.76 mmol). After 30 minutes iodomethane (0.30 mL, 4.76 mmol) is added and the solution stirred for 1 hour. The solution is diluted with Et2O (30 mL), washed with water (2×20 mL), brine (20 mL) dried over MgSO4, filtered and concentrated. The residue is purified by ISCO (2%-5% EtOAc gradient) to furnish the title compound (0.33 g, 1.76 mmol, 41%). 1H NMR (CDCl3), δ 1.42 (d, J=6.5 Hz, 6H), 2.43 (s, 3H), 3.84-3.91 (m, 1H), 6.24-6.27 (m, 1H), 3.93 (s, 1H), 6.29 (s, 1H), 7.01-7.14 (m, 1H), 7.38 (d, J=7.5 Hz, 1H) ppm. LC/MS (m/z): calcd. for C13H17N (M+H)+: 188.2. found: 188.1.

Workup

  1. washwashed with water (2×20 mL), brine (20 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by ISCO (2%-5% EtOAc gradient)

Sources & evidence

ORD record
ord-6b0bd9689b194edca7ad7e6387f02f85
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

Loading…