Benzyl chloroformate → Benzyl 1H-indol-6-ylcarbamate

HRID 2361256Notes

Reaction equation

HRID 2361256 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:10])[CH:8]=2)[CH:3]=[CH:2]1.[C:11](Cl)(=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CCCCCC>O1CCCC1.C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 2560966-AminoindoleHCID 21226206Ethyl acetate hexane

Product 1

HCID 67994742Benzyl 1H-indol-6-ylcarbamateYield 52.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1H-indol-6-amine (1.0 g, 7.57 mmol), benzyl carbonochloridate (1.421 mL, 9.46 mmol), and potassium carbonate (1.307 g, 9.46 mmol) in tetrahydrofuran (50 mL) was stirred at room temperature for 16 hr. The mixture was diluted with ethyl acetate (150 mL) and insoluble material was removed by filtration. The filtrate was washed sequentially with saturated NaHCO3 solution (50 mL) and brine (50 mL). The organic solution was dried over anhydrous MgSO4. The desired product (1.05 g, 3.94 mmol, 52.1% yield) was isolated as a white solid by ISCO (120 g silica gel, solid loading, 5-30% ethyl acetate/hexane).

Workup

  1. customwas removed by filtration
  2. washThe filtrate was washed sequentially with saturated NaHCO3 solution (50 mL) and brine (50 mL)
  3. dry with materialThe organic solution was dried over anhydrous MgSO4

Sources & evidence

ORD record
ord-0887b02b50bd46cfae99b2696a258b2d
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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