HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Fluoro-6-(tributylstannyl)pyridine → 9-tert-butyl-2-(6-fluoropyridin-2-yl)-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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Fluoro-6-(tributylstannyl)pyridine | HCID 16427115 | — |
| 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-2-(6-fluoropyridin-2-yl)-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 58124827 | 72.7% |
Reaction Steps
A solution of 80 mg of 11i, 90 mg of 2-fluoro-6-tributylstannylpyridine and 25 mg of Pd(PPh3)4 in 5 ml of degassed toluene was heated at 110° C., under N2 atmosphere, during 48 hr. The reaction mixture was applied to a silica gel column and eluted with a gradient of heptane/acetone. The isolated product was treated with diethyl ether and provided 60 mg of 11k as white crystalline material; Mp: 232-234° C.; Rf 0.45 (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-d6538c7df5314856a96a68833c2cf047 |
| Source note | uspto-grants-2013_04 |