Methanol → 7,7-Dimethyl-2-methylamino-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

HRID 2235467Notes

Reaction equation

HRID 2235467 reaction equation
[Na].[NH2:2][C:3]1[NH:22][C:6]2=[CH:7][C:8]3[C:9]([CH3:21])([CH3:20])[C:10](=[O:19])[N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:12]=3[CH:13]=[C:5]2[N:4]=1.[BH4-].[Na+].[CH3:25]O>O>[CH3:20][C:9]1([CH3:21])[C:8]2[CH:7]=[C:6]3[NH:22][C:3]([NH:2][CH3:25])=[N:4][C:5]3=[CH:13][C:12]=2[N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:10]1=[O:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 5360545SodiumHCID 593008242-Amino-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

Product 1

HCID 674266807,7-Dimethyl-2-methylamino-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Freshly cut sodium (300 mg) is dissolved in dry MeOH (12 ml) and D5 (700 mg) is added and the mixture stirred for 5 min. Then p-formaldehyde (102 mg; 3.4 mmol) is added and the mixture stirred for 20 h at RT. After the addition of NaBH4 (93 mg; 2.46 mmol) the solution is heated under reflux for 2 h, cooled to RT and diluted with water. The aqueous layer is extracted with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4 and concentrated in vacuo. The compound (700 mg) is obtained by flash chromatography on silica gel eluted with CH2Cl2/MeOH (95:5).

Workup

  1. stirringthe mixture stirred for 20 h at RT
  2. temperatureis heated
  3. temperatureunder reflux for 2 h
  4. extractionThe aqueous layer is extracted with EtOAc
  5. washThe combined organic layer is washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3fc54c40a5f3424aa0c8927817497123
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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