Trifluoroacetic acid → HCID 12700064, compound

HRID 2360114Notes

Reaction equation

HRID 2360114 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[CH:6]2.FC(F)(F)C(O)=O.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH3:1][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

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 8198645-methoxy-1-methyl-1H-indoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 12700064HCID 12700064, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-methoxy-1-methylindole (182 mg, 1.13 mmol) in 2.3 mL of acetic acid was added trifluoroacetic acid (1.1 mL). After the reaction mixture was added sodium cyanoborohydride (142 mg, 2.26 mmol) at 0° C., the reaction mixture was stirred at the same temperature for 2 h. After the reaction mixture was basified by 50% sodium hydroxide aqueous solution, the solution was extracted with diethyl ether (20 mL) twice. The combined extracts were washed with brine (5 mL), 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=95/5 to 80/20) to obtain 5-methoxy-1-methylindoline (131 mg, 71%).

Workup

  1. extractionthe solution was extracted with diethyl ether (20 mL) twice
  2. washThe combined extracts were washed with brine (5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)

Sources & evidence

ORD record
ord-d942d69d7aa6448b83132436b1ad0ddd
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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