HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490567Generated: October 30, 2026
1-Boc-indole → tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate
https://huagongshe.com/reaction/1490567
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1-Boc-indole | HCID 3532980 | — |
| Reagent | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reagent | 3-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaborole | HCID 122380799 | — |
| Catalyst | Bis(1,5-cyclooctadiene)dimethoxydiiridium | HCID 76001521 | — |
| Solvent | Cyclopentyl methyl ether | HCID 138539 | — |
| Product | tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate | HCID 49758860 | 65% |
Reaction Steps
The general procedure A was followed using tert-butyl 1H-indole-1-carboxylate (108.7 mg, 0.5 mmol.) and B2(pin)2 (101.6 mg, 0.4 mmol, 0.8 eq.) as starting material. The resulting mixture was allowed to stir 16 hours at 75 oC. 5z was obtained as white solid (111.5 mg, 65 %) after purification by silica gel flash chromatography (EtOAc/PE=1:30 v/v). m.p.: 163-165 oC.
Provenance & Evidence
| DOI | 10.1021/jacs.5b05252 |
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| Source dataset | Borylation dataset from Roche |
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| ORD ID | ord-79db2c6eef514d27b2130b1758eb40ff |
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| Source note | Borylation dataset from Roche |
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