HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490499Generated: October 30, 2026
1-Methyl-2,3-dihydro-1H-indole → 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indole
https://huagongshe.com/reaction/1490499
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1-Methyl-2,3-dihydro-1H-indole | HCID 55830 | — |
| Reagent | Pinacol | HCID 6425 | — |
| Reagent | Triethylamine | HCID 8471 | — |
| Reagent | Norbornadiene | HCID 8473 | — |
| Reagent | Catecholborane | HCID 67506 | — |
| Catalyst | Tris(pentafluorophenyl)borane | HCID 582056 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indole | HCID 24229591 | 30% |
Reaction Steps
Prepared from 1-methylindoline (1j, 13.5 mg, 0.100 mmol, 1.00 equiv), catBH (24.0 mg, 0.200 mmol, 2.00 equiv), norbornadiene (9.2 mg, 0.10 mmol, 1.00 equiv) and B(C6F5)3 (5.1 mg, 0.010 mmol, 0.10 equiv) according to GP 3. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 3j (7.5 mg, 30%) as a white solid.
Provenance & Evidence
| DOI | 10.1002/anie.201611536 |
|---|
| Source dataset | Borylation dataset from Roche |
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| ORD ID | ord-a69ae003920743bcb48cb3ac16966ce5 |
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| Source note | Borylation dataset from Roche |
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