Triethylamine → benzyl 1h-indol-5-ylcarbamate
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(N(CC)CC)C.C([CH:21]([O:28]Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(O)=O.[C:30]([O-])([O-])=[O:31].[Na+].[Na+]>C(#N)C>[C:22]1([CH2:21][O:28][C:30](=[O:31])[NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
To a solution of 5-aminoindole (10.0 g, 76 mmol) and triethylamine (7.67 g, 76 mmol) in acetonitrile (400 mL) at 0° C. was added dropwise a solution of carboxybenzyloxychloride (12.93 g, 75.8 mmol) in acetonitrile (80 mL). After the addition was complete the reaction was allowed to warm to 23° C. and stand for 60 h. The solvent was removed in vacuo and the residue treated with water containing Na2CO3 (76 mmol). The mixture was extracted with four portions of CH2Cl2. The combined organic extracts were washed with a saturated NaCl solution, dried with K2CO3, filtered, and concentrated in vacuo. Silica gel chromatography (4:1 to 1:1 hexane:ethyl acetate gradient) of the concentrate afforded phenylmethyl-(1H-indol-5-yl)carbamate (5.11 g, 25%).
Workup
- additionAfter the addition
- customThe solvent was removed in vacuo
- additionthe residue treated with water
- extractionThe mixture was extracted with four portions of CH2Cl2
- washThe combined organic extracts were washed with a saturated NaCl solution
- dry with materialdried with K2CO3
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c41b0e472eb64cc4b7faa208a4d71baf
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05434154
Reaction notes
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