Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 1,4-Dibromobutane | HCID 8056 | — |
| Reactant | HCID 54313644 | HCID 54313644 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 18932905 | HCID 18932905 | 16.6% |
Reaction Steps
To 1-(6,7-dimethoxy-quinazolin-4-yl)-2,3-dihydro-1H-indol-6-ylamine (103 mg, 0.320 mmol; from Example 30) in DMF (4 mL) was added 1,4-dibromo-butane (42 μL, 0.352 mmol) and pyridine (34 μL, 0.64 mmol) and the mixture was heated to 110° C. for 36 hours under N2(g). The mixture was diluted with saturated aqueous NaHCO3 and extracted with EtOAc/Et2O (1:1) and the organic phase was washed with water and brine, dried over Na2SO4(s), filtered and concentrated in vacuo. The residue was chromatographed on silica (4% MeOH/CHCl3) to afford 20 mg of product. (M.P. 198°-205° C. (dec); GC-MS: 376 (M+); anal. RP18-HPLC RT: 5.05 min.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05736534 |
|---|
| Source dataset | uspto-grants-1998_04 |
|---|
| ORD ID | ord-e1a0bdb884de4813a4ede4beeec36d60 |
|---|
| Source note | uspto-grants-1998_04 |
|---|