Methanol → HCID 86659887, compound

HRID 2360166Notes

Reaction equation

HRID 2360166 reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[C:5]([CH2:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17]C)[CH:15]=2)[N:10]([CH3:19])[CH2:9]1)=[O:6])[CH2:2][CH3:3].B(Br)(Br)Br.CO>ClCCl.C(OCC)C>[CH2:20]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([CH2:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[N:10]([CH3:19])[CH2:9]1)=[O:6])[CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 86659886HCID 86659886, compound

Product 1

HCID 86659887HCID 86659887, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(di-n-propylaminocarbonylmethyl)-5-methoxy-1-methylindoline (62 mg, 0.20 mmol) in 1.0 mL of dry dichloromethane was added boron tribromide (0.116 mL, 1.20 mmol) at 0° C. After the reaction mixture was stirred at room temperature for 30 min, methanol (0.2 mL) was added. After the reaction mixture was diluted with diethyl ether, the solution was washed with saturated NaHCO3 aqueous solution and brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo to obtain crude 3-(di-n-propylaminocarbonylmethyl)-1-methylindolin-5-ol. The title compound was synthesized using the same procedure employed for Example 2 (2), but with the above product instead of 1-benzylindolin-5-ol. The product was obtained as a white solid (28.6 mg, 2 steps 32%) having the following characteristics.

Workup

  1. washthe solution was washed with saturated NaHCO3 aqueous solution and brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3ee8a59b007e415489dbac22197529a4
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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