Triethylamine → Ethyl 3-chloro-4-(3-indolylcarbonylamino)phenylacetate

HRID 1372599Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[CH:2]1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][C:15]=1[Cl:26].C(N(CC)CC)C>O>[Cl:26][C:15]1[CH:16]=[C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:18]=[CH:19][C:14]=1[NH:13][C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[O:12]

Participants

Conditions

Temperature: 70 °C

Procedure

EDC•HCL (1.78 g, 9.28 mmol) was added to a solution of indole-3-carboxylic acid (1.00 g, 6.21 mmol), ethyl 4-amino-3-chlorophenylacetate (1.33 g, 6.22 mmol) and triethylamine (1.80 mL, 12.9 mmol). The mixture was stirred at 70° C. for 24 hours. After cooling to room temperature, the reaction mixture was added with water (30 ml), followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (1:1, v/v) eluate fractions, ethyl 3-chloro-4-(3-indolylcarbonylamino)phenylacetate (1.25 g, 56%) was obtained as a pale yellow solid.

Workup

temperatureAfter cooling to room temperature
extractionfollowed by extraction with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
distillationdistilled under reduced pressure
customto remove the solvent
customThe residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (1:1

Sources & evidence

ORD record: ord-49eed944d4ce442b9151eecd8c02f343
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157487B2

Reaction notes

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