Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | HCID 22032964 | HCID 22032964 | — |
| Product | HCID 86588620 | HCID 86588620 | 84% |
Reaction Steps
Ethyl {1-benzyl-5-[3-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetate was prepared from 1-benzyl-5-[3-(trifluoromethoxy)phenyl]-1H-indole (1.06 g, 2.89 mmol), oxalyl chloride (1.04 mL, 13.0 mmol), and ethanol (1.5 mL), following the procedure described in Step 3 of Example 1. Purification by flash chromatography using 5-10% ethyl acetate in hexane as an eluant yielded the title compound as a light brown gum (1.14 g, 84%). Mass spectrum (+ESI, [M+H]+) m/z 468; 1HNMR (500 MHz, DMSO-d6): δ 8.75 (s, 1H), 8.45 (d, 1H, J=1.4 Hz), 7.7 (m, 2H), 7.6-7.65 (m, 3H), 7.25-7.4 (m, 6H), 5.65 (s, 2H), 4.35 (q, 2H, J=7.1 Hz), and 1.35 ppm (t, 3H, J=7.2 Hz). Elemental Analysis for C26H20F3NO4: Calculated: C, 66.81; H, 4.31; N, 3.00. Found: C, 66.82; H, 4.28; N, 2.98.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07368471B2 |
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| Source dataset | uspto-grants-2008_05 |
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| ORD ID | ord-91b570e5edc549aba21426eac312b82a |
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| Source note | uspto-grants-2008_05 |
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