Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Chloromethyl pivalate | HCID 87885 | — |
| Reactant | Vemurafenib | HCID 42611257 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 73387843 | HCID 73387843 | 24.8% |
Reaction Steps
To a mixture of N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide (0.1 g, 0.2 mmol) and Et3N (57 μL, 0.41 mmol) in DMF (1 mL) was added chloromethyl pivalate (35 μL, 0.25 mmol) at rt. The reaction was stirred at rt for 24 h, then concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=4/1 to 1/1) to afford (5-(4-chlorophenyl)-3-(2,6-difluoro-3-(propylsulfonamido)benzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl pivalate (30 mg, 23%) and (N-(3-(5-(4-chlorophenyl)-1-((pivaloyloxy)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl) propylsulfonamido) methyl pivalate (20 mg, 13.3%) as white solids. The title compounds were characterized by LC-MS and 1H NMR as shown below:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09399639B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-c0fea9c56fd541edb691a0d1eb8022fc |
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| Source note | uspto-grants-2016_07 |
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