Water → benzyl 1H-indole-3-carboxylate

HRID 1527155Notes

Reaction equation

HRID 1527155 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:11][C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[O:12])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 69867Indole-3-Carboxylic Acid

Product 1

HCID 8605861benzyl 1H-indole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1H-indole-3-carboxylic acid (5 g, 31 mmol) in DMF (70 mL) under nitrogen atmosphere at 0° C. was added cesium carbonate (11 g, 31 mmol) and benzyl bromide (4.05 mL, 34.1 mmol). The reaction mixture was stirred at RT for 48 h and poured into water. EtOAc was added and the layers were separated, the aqueous one being back extracted three times with EtOAc. The combined organic layers were washed with water, dried over Na2SO4, filtered and concentrated. The residue was taken up in Et2O and the resulting precipitate was filtered-off to give the title compound. TLC, Rf (c-hexane/EtOAc 1:1)=0.55; MS (LC-MS): 252.1 [M+H]+, 274.0 [M+Na]+, 525.1 [2M+Na]+, 250.1 [M−H]−; tR (HPLC conditions a) 3.77 min.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous one being back extracted three times with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ef642756622745b08f44615953fada24
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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