Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N,N-Dimethylpropargylamine | HCID 81643 | — |
| Reactant | Ethyl acetate methanol triethylamine | HCID 21980445 | — |
| Reactant | HCID 23393847 | HCID 23393847 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1H-Indolamine | HCID 122074 | 62.3% |
Reaction Steps
2-Methyl-5-(nonafluorobutane-1-sulfonyloxy)-1H-indole-3-carboxylic acid benzyl ester (0.480 g, 0.85 mmol, 1 eq, Example 52, Step A) was dissolved in dry THF (10 mL) under Ar. Triethylamine (0.223 mL, 1.6 mmol, 2.0 eq) was added followed by the addition of copper (1) iodide (0.008 g, 0.04 mmol, 5 mol %), dichloropalladium (II) bis-diphenylphosphinoferrocene (0.016 g, 0.02 mmol, 2 mol %), and N,N-dimethylpropargylamine (0.184 mL, 1.6 mmol, 2 eq). The reaction mixture was stirred at 80° C. and followed by TLC (ethyl acetate/methanol/triethylamine 87/10/3). After 48 hours, the reaction was loaded on silica gel and chromatographed, (ethyl acetate/methanol/triethylamine 87/10/3). The resulting product was contaminated with bis-alkyne side product, and was further purified using reverse-phase prep-HPLC 10%-1 00% Acetonitrile/water, 0.1% TFA. 0.070 g (18% yield) of the indole-amine was obtained as a brown semisolid: LC/MS (ESI+) 347 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06951848B2 |
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| Source dataset | uspto-grants-2005_10 |
|---|
| ORD ID | ord-15469e4b1a1d4bd7a32ac78f32e93b0c |
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| Source note | uspto-grants-2005_10 |
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