HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chloroform → HCID 66988923, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Hydroxymethyl)benzeneboronic acid | HCID 2734706 | — |
| Reactant | 6-((3-Bromophenyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide | HCID 66988260 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 66988923 | HCID 66988923 | 68% |
Reaction Steps
To a suspension of Intermediate 62 (0.95 mmol) and 4-(hydroxymethyl)phenylboronic acid (290 mg, 1.90 mmol) in DME (10 mL) at room temperature was added 2 M Na2CO3 (1.4 mL, 2.85 mmol) and PdCl2(PPh3)2 (33 mg, 0.005 mmol). The reaction mixture was stirred at reflux for 2 h and then cooled to room temperature. After the addition of 60 mL of chloroform, a white precipitate formed which was collected by filtration. The crude product was purified by flash column chromatography (0-15% MeOH in dichloromethane) to give the title compound (357 mg, 68% for 3 steps). ES/MS calcd. for C31H28N3O5S+ 554.2. Found m/z=554.3 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394829B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-fdb110c740ee49648ddd3c1ba0af73e0 |
| Source note | uspto-grants-2013_03 |