HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-(Tributylstannyl)-1,3-thiazole → 9-tert-butyl-3-methoxy-2,14-di-1,3-thiazol-5-yl-5,6,10,11-tetrahydro-9H-[1,4]oxazocino[7',6':4,5]pyrrolo[2,1-a]isoquinolin-8(13H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-(Tributylstannyl)-1,3-thiazole | HCID 2763257 | — |
| Reactant | 2-bromo-9-tert-butyl-3-methoxy-14-(1,3-thiazol-5-yl)-5,6,10,11-tetrahydro-9H-[1,4]oxazocino[7',6':4,5]pyrrolo[2,1-a]isoquinolin-8(13H)-one | HCID 58124817 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 9-tert-butyl-3-methoxy-2,14-di-1,3-thiazol-5-yl-5,6,10,11-tetrahydro-9H-[1,4]oxazocino[7',6':4,5]pyrrolo[2,1-a]isoquinolin-8(13H)-one | HCID 58124786 | 76.9% |
Reaction Steps
A degassed solution of 40 mg of 11i, 45 mg of 5-tributylstannyl thiazole and 15 mg of Pd(PPh3)4 in 3 ml of toluene was heated at 110° C. during 5 hr. The reaction mixture was concentrated and the residue was chromatographed over silica gel, using a gradient of toluene/acetone as eluent. The isolated product was treated with diethyl ether, to provide 31 mg of 11l as white crystalline material; Mp: 254-255° C.; Rf 0.30 (heptane/acetone 1/1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08431564B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-f9e46fe6e3a34c7ebca25064663b4419 |
| Source note | uspto-grants-2013_04 |