Methanol → HCID 21029540, compound

HRID 2360115Notes

Reaction equation

HRID 2360115 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH2:7][CH2:6]2.B(Br)(Br)Br.CO.C([O-])(O)=O.[Na+]>ClCCl>[CH3:12][N:8]1[C:9]2[C:5](=[CH:4][C:3]([OH:2])=[CH:11][CH:10]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 12700064HCID 12700064, compound

Product 1

HCID 21029540HCID 21029540, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methoxy-1-methylindoline (131 mg, 0.802 mmol) in 4.0 mL of dry dichloromethane was added boron tribromide (0.38 mL, 4.0 mmol) under nitrogen at 0° C. After the reaction mixture was stirred at the same temperature for 30 min, methanol (1 mL) was added with additional stirring at room temperature for 5 min. After the reaction mixture was neutralized by saturated NaHCO3 aqueous solution, the solution was extracted with diethyl ether (20 mL) twice. The combined extracts were washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 50/50) to obtain the title compound (63 mg, 53%).

Workup

  1. stirringwith additional stirring at room temperature for 5 min
  2. extractionthe solution was extracted with diethyl ether (20 mL) twice
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 50/50)

Sources & evidence

ORD record
ord-6f1411dac93b49a7b2e0fede3196720d
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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