Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 118093663 | HCID 118093663 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 118093679 | HCID 118093679 | 99.3% |
Reaction Steps
A solution of 4-[2-(2,4-difluorophenoxy)-4-(methylamino)-5-nitrophenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (0.150 g, 0.258 mmol) in ethyl acetate (1.0 mL) was treated with methanol (1.0 mL) and saturated aqueous ammonium chloride solution (0.225 mL, 3.36 mmol) and cooled to 0° C. The reaction mixture was treated with zinc (0.135 g, 2.07 mmol) in two portions over 5 minutes. The reaction mixture was heated at 55° C. for 10 min, diluted with dichloromethane, filtered over Celite, and washed with dichloromethane. The filtrate was concentrated to residue. The residue was dissolved in dichloromethane (30 mL), washed with saturated sodium bicarbonate solution (20 mL), dried with sodium sulfate, filtered, and concentrated to give the desired product (0.141 g, 99%), which was used without further purification. LCMS calculated for C28H25F2N4O4S (M+H)+: m/z=551.2. found: 550.9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09315501B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-9e7196e2ad0b4069a7773fb27be28e78 |
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| Source note | uspto-grants-2016_04 |
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