Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 5-Chloro-1H-indole-2-carboxylic acid | HCID 82693 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22612547 | HCID 22612547 | 6.3% |
Reaction Steps
5.52 g of 5-chloro-2-indolecarboxylic acid are dissolved in 40 ml of DMF, 4.57 g of carbonyldiimidazole are added at RT, under nitrogen, the mixture is then heated to 40° C and 4.3 g of DBU and 4.17 g of tertbutanol are added. Heating is continued at 40° C. for 3 hours, the precipitate formed is then filtered off and the filtrate is concentrated under vacuum. The residue is taken up in EtOAc, washed with 10% Na2CO3 solution, with saturated aqueous NaCl, with sulphate buffer and then dried over Na2SO4 and concentrated. The residue is chromatographed on silica, eluting with DCM, to give 0.45 g of the expected compound: m.p.=140-142° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06380230B1 |
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| Source dataset | uspto-grants-2002_04 |
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| ORD ID | ord-41c3147bbdfa43ec9dd93596d8f154ae |
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| Source note | uspto-grants-2002_04 |
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