HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl 2,3-dihydro-2-oxo-1H-indole-5-carboxylate → 2-Hydroxy-3-(5,6,7,8-tetrahydroquinazolin-4-yl)-1H-indole-5-carboxylic Acid Methyl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl 2,3-dihydro-2-oxo-1H-indole-5-carboxylate | HCID 2773516 | — |
| Reactant | 4-Chloro-5,6,7,8-tetrahydroquinazoline | HCID 12582969 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Product | 2-Hydroxy-3-(5,6,7,8-tetrahydroquinazolin-4-yl)-1H-indole-5-carboxylic Acid Methyl Ester | HCID 136351946 | — |
Reaction Steps
The title compound was synthesized according to the procedure described for Example 9 using sodium tert-butoxide (48 mg, 0.5 mmol), methyl 2-oxo-5-indolinecarboxylate (21 mg, 0.11 mmol) and 4-chloro-5,6,7,8-tetrahydroquinazoline solution (0.1 mL, 1 M in N-methylpyrrolidinone, corresponding to 17 mg, 0.1 mmol; described in: Budesinsky Z., Roubinek F. Collect. Czech. Chem. Commun., 1964, 29, 2341). The crude oil was purified on SCX-column pre-rinsed with methanol using ethyl acetate, methylene chloride, methylene chloride/methanol 1:1, and methanol/ammonia (2 M, aq) as elution solvents.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07205314B2 |
| Source dataset | uspto-grants-2007_04 |
| ORD ID | ord-6f53902b6e3e48fda8c0489b0321e917 |
| Source note | uspto-grants-2007_04 |