Acetic Acid → 1-(4-Methoxybenzyl)indolin-5-yl 4-isopropylphenylcarbamate

HRID 2360137Notes

Reaction equation

HRID 2360137 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:22])[O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH2:17][CH2:16]3)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1.C(O)(=O)C.[Na].C([O-])(O)=O.[Na+]>ClCCl.C(OCC)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:22])[O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)[CH2:17][CH2:16]3)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 312444-MethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 86659865Indolin-5-yl 4-isopropylphenylcarbamate

Product 1

HCID 866598661-(4-Methoxybenzyl)indolin-5-yl 4-isopropylphenylcarbamateYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of indolin-5-yl 4-isopropylphenylcarbamate (15.0 mg, 50.6 μmol) in 0.75 mL of dry dichloromethane was added 4-methoxybenzaldehyde (12.3 μL, 0.101 mmol) at room temperature. After the reaction mixture was stirred at the same temperature for 2 min, acetic acid (29 μL, 0.51 mmol) and sodium triacetoxyhydroborate (38 mg, 0.18 mmol) was added, successively. After the reaction mixture was stirred at the same temperature for 30 min, the reaction mixture was diluted with diethyl ether (2 mL). After the reaction mixture was neutralized by saturated NaHCO3 aqueous solution (1 mL), the organic layer was separated. The separated organic layer 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 as a white solid (17.2 mg, 82%).

Workup

  1. stirringAfter the reaction mixture was stirred at the same temperature for 30 min
  2. customthe organic layer was separated
  3. concentrationThe separated organic layer was concentrated in vacuo
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 50/50)

Sources & evidence

ORD record
ord-7be1648dfde04063b87cd26a82062301
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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