Water → benzyl 1H-indole-3-carboxylate

HRID 1052094Notes

Reaction equation

HRID 1052094 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 a 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 and the aqueous layer was extracted with EtOAc (×3). 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 layer was extracted with EtOAc (×3)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-46af06467be4498280e557a7010e17ea
Source dataset
uspto-grants-2016_07
Patent number
US09388199B2

Reaction notes

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