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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1971695Generated: October 31, 2026

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

https://huagongshe.com/reaction/1971695

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-(Tributylstannyl)-1,3-thiazoleHCID 2763257—
Reactant2-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)-oneHCID 58124817—
CatalystHCID 178418397HCID 178418397—
SolventTolueneHCID 1140—
Product9-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)-oneHCID 5812478676.9%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08431564B2
Source datasetuspto-grants-2013_04
ORD IDord-f9e46fe6e3a34c7ebca25064663b4419
Source noteuspto-grants-2013_04