Dichloromethane → methyl 6-hydroxy-1H-indole-2-carboxylate

HRID 1171214Notes

Reaction equation

HRID 1171214 reaction equation
ClCCl.[CH3:4][O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([O:17]C)[CH:11]=2)=[O:7].B(Br)(Br)Br>O>[CH3:4][O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([OH:17])[CH:11]=2)=[O:7]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 688173Methyl-6-methoxy-2-indolecarboxylate

Product 1

HCID 10535709methyl 6-hydroxy-1H-indole-2-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a dichloromethane (10 mL) solution of 6-methoxy-1H-indole-2-carboxylic acid methyl ester (500 mg, 2.44 mmol) was added boron tribromide (12.2 mL, 12.2 mmol) at −78° C., which was stirred for 50 minutes at 0° C. under nitrogen atmosphere. To the reaction solution was added water at 0° C. followed by extraction with ethyl acetate. The organic layer was washed with sat. NaCl followed by drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (395 mg, 85%) as a white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with sat. NaCl
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a9cc46d590d244bd960aafe109635e17
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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