Sodium Carbonate → HCID 60153287, compound

HRID 1475316Notes

Reaction equation

HRID 1475316 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:18](OC([O-])=O)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>C1COCC1>[C:21]([O:20][C:18]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)[CH2:6][C:7]1=[O:11])=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 22064466Tert-butyldicarbonate

Product 1

HCID 60153287HCID 60153287, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 6-chloro-1,3-dihydro-indol-2-one (11.35 g, 67.7 mmol), sodium carbonate (35.9 g, 338.5 mmol), tert-butyl dicarbonate (36.7 g, 168.2 mmol) and THF (300 mL) was stirred at 20° C. for 88 h then solids were removed by filtration and the filtrate evaporated in vacuo to give an oil. Chromatography (SiO2; gradient elution with 5-25% EtOAc in petrol) gave the title compound (8.746 g) as an oil. MS: [M−H]−=266.

Workup

  1. customsolids were removed by filtration
  2. customthe filtrate evaporated in vacuo
  3. customto give an oil
  4. washChromatography (SiO2; gradient elution with 5-25% EtOAc in petrol)

Sources & evidence

ORD record
ord-ba48c98c2a0b427db640bb622e8515d6
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

Loading…