Water → HCID 89451879, compound

HRID 1497541Notes

Reaction equation

HRID 1497541 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([O:13][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 191033376-Hydroxy-1H-indole-3-carboxylic acid

Product 1

HCID 89451879HCID 89451879, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-hydroxy-1H-indole-3-carboxylic acid (1.05 g) in N,N-dimethylformamide (11.0 mL) were added sodium carbonate (722 mg) and benzyl bromide (0.775 mL), followed by stirring at room temperature overnight. To the reaction suspension was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain benzyl 6-hydroxy-1H-indole-3-carboxylate (1.04 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-20769ae84d64439fa6b6ce1ea9bd5c25
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

Loading…