Methanol → HCID 131726447, compound

HRID 1351948Notes

Reaction equation

HRID 1351948 reaction equation
C(N(CC)[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][C:16]([O:18]C)=O)=O)C.[BH4-].[Na+].[CH3:24][OH:25]>O1CCCC1>[CH2:12]([N:13]([CH2:14][CH3:6])[C:24]([CH2:4][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][CH2:16][OH:18])=[O:25])[CH3:11]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 4311764Sodium borohydrideHCID 85905916HCID 85905916, compound

Product 1

HCID 131726447HCID 131726447, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (7-((diethylamino)carbonyl)-1H-indol-3-yl)acetate (1.87 g, 6.48 mmol) in tetrahydrofuran (30 mL) are added sodium borohydride (1.35 g, 35.7 mmol) and methanol (5 mL) under nitrogen atmosphere, and the mixture is stirred at room temperature for 24 hours, and then refluxed for 4 hours. The mixture is cooled to room temperature, and methanol is added to the reaction solution. The solvent is evaporated, and the residue is separated into water and chloroform. The organic layer is washed with a saturated brine, and dried over anhydrous magnesium sulfate. The solvent is evaporated, and the obtained crude product is purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→ethyl acetate ethyl acetate:methanol=5:1) to give N,N-diethyl-3-(2-hydroxyethyl)-1H-indole-7-carboxyamide (1.56 g, 5.99 mmol, yield: 92%).

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureThe mixture is cooled to room temperature
  3. customThe solvent is evaporated
  4. customthe residue is separated into water and chloroform
  5. washThe organic layer is washed with a saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent is evaporated
  8. customthe obtained crude product
  9. customis purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→ethyl acetate ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-c8f62d9d93514e3d8ffcd2884c7e827f
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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