Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | HCID 59199239 | HCID 59199239 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Product | HCID 59199232 | HCID 59199232 | — |
Reaction Steps
A mixture of 2-(4-sulfamoylphenylamino)quinazolin-8-yl trifluoromethanesulfonate (900 mg, 2 mmole), Pd(dppf)Cl2 (170 mg, 0.2 mmole), triethylamine (700 ul, 5 mmole) and triethylsilane (960 ul, 6 mmole) in DMF (20 ml) was placed in a stainless steel reactor. CO was bubbled into the mixture in the reactor. The reaction solution was stirred at 85° C. under CO (420 psi) for overnight. The reaction mixture was poured into 80 ml of saturated NaHCO3 and extracted with ethyl acetate (2×250 ml). The combined organic layers were washed with water (2×60 ml) and brine (60 ml), then dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash column chromatography to give 4-(8-formylquinazolin-2-ylamino)benzenesulfonamide (274 mg, 0.83 mmole) as brown solid. ES/MS m/z 328.9 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07932262B2 |
|---|
| Source dataset | uspto-grants-2011_04 |
|---|
| ORD ID | ord-095ffb9fb18a46138248570a7aee7880 |
|---|
| Source note | uspto-grants-2011_04 |
|---|
