Sodium Hydroxide → HCID 4566228, compound

HRID 717779Notes

Reaction equation

HRID 717779 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:5]2.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 832471H-Indole, 5-methyl-2-phenyl-HCID 5003444Sodium cyanoborohydride

Product 1

HCID 4566228HCID 4566228, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 5-methyl-2-phenyl-1H-indole (0.96 g, 0.00463 mol) in acetic acid (28.8 mL) was added sodium cyanoborohydride (0.873 g, 0.0139 mol) at RT and the resulting reaction mixture was stirred for 4 h. After completion of reaction (monitored by TLC), the reaction mixture was basified with sodium hydroxide solution and extracted with EtOAc (3×150 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (2% ethylacetate:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx 0.5 inch) to provide the desired compound as a brown colored oil (0.7 g, 72% yield).

Workup

  1. customthe resulting reaction mixture
  2. customAfter completion of reaction (monitored by TLC)
  3. extractionextracted with EtOAc (3×150 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (2% ethylacetate:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx 0.5 inch)

Sources & evidence

ORD record
ord-21ac3f248b7d4315a40bc00af2b1e891
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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