HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 387334Generated: October 26, 2026
Potassium Carbonate → 5-[3-({[(1S)-1,2-Dimethylpropyl]amino}methyl)phenyl]-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide
https://huagongshe.com/reaction/387334
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-Formylphenylboronic acid | HCID 2734356 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | 1,2-Dimethylpropylamine, (S)- | HCID 6999788 | — |
| Reactant | 5-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide | HCID 59332757 | — |
| Catalyst | Zincchloride | HCID 3007855 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 5-[3-({[(1S)-1,2-Dimethylpropyl]amino}methyl)phenyl]-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide | HCID 59332623 | 15.8% |
Reaction Steps
To 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (80 mg, 0.216 mmol) in dioxane and water (4 mL/1 mL) was added (3-formylphenyl)boronic acid (45 mg), Pd(PPh3)4 (25 mg) and K2CO3 (104 mg). The reaction mixture was redissolved in DMSO (2 mL). To the resultant mixture zinc chloride (30 mg), NaCNBH3 (30 mg) and (2s)-3-methyl-2-butanamine (50 mg) were added. The mixture was heated to 100° C. for 30 minutes by microwave irradiation and purified by HPLC with TFA to afford the title compound (16 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08372875B2 |
|---|
| Source dataset | uspto-grants-2013_02 |
|---|
| ORD ID | ord-3efe24c9dd274a2799499dd6eb621f4e |
|---|
| Source note | uspto-grants-2013_02 |
|---|
