Boron tribromide → HCID 68564618, compound

HRID 1786466Notes

Reaction equation

HRID 1786466 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15]C)=[C:10]([CH3:17])[CH:9]=2)=[O:5])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[C:10]([CH3:17])[CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10889813HCID 10889813, compound

Product 1

HCID 68564618HCID 68564618, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.13 g (0.56 mmol) 5-methoxy-6-methyl-1H-indole-2-carboxylic acid ethyl ester in 3 mL dichloromethane was cooled to −78° C. 1.11 mL (1.1 mmol, 1 M solution in dichloromethane) boron tribromide were added and the cooling bath was removed. After stirring 2 h at room temperature, the solution was poured into 10% aqueous sodium bicarbonate solution and the phases were separated. The aqueous layer was extracted three times with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using a gradient of n-heptane: ethyl acetate (100:0 to 70:30 v/v) as eluant, to afford 53 mg (43%) of the title compound as a light-yellow solid.

Workup

  1. customthe cooling bath was removed
  2. additionthe solution was poured into 10% aqueous sodium bicarbonate solution
  3. customthe phases were separated
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography on silica gel using a gradient of n-heptane: ethyl acetate (100:0 to 70:30 v/v) as eluant

Sources & evidence

ORD record
ord-83b1e8e5275742b29be9677410a23816
Source dataset
uspto-grants-2009_03
Patent number
US07507736B2

Reaction notes

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