Reaction equation
CNC(=O)OC(C)(C)C.O=c1cc(N2CCOCC2)oc2c(-c3cccc4c3sc3ccc(OS(=O)(=O)C(F)(F)F)cc34)cccc12>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>CN(C(=O)OC(C)(C)C)c1ccc2sc3c(-c4cccc5c(=O)cc(N6CCOCC6)oc45)cccc3c2c1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 140 °C
Procedure
6-(2-morpholino-4-oxo-4H-chromen-8-yl)dibenzo[b,d]thiophen-2-yl trifluoromethanesulfonate (207.4 mg, 0.37 mmol), tert-butyl methylcarbamate (194 mg, 1.48 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (10.69 mg, 0.02 mmol) and cesium carbonate (481 mg, 1.48 mmol) were suspended in dioxane (6 mL) and sealed into a microwave tube. The reaction was heated to 140 °C for 1 hour in the microwave reactor and cooled to RT. The reaction mixture was filtered then silica gel (2 g) added. The mixture was concentrated _in vacuo_ to yield a white powder which was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford tert-butyl methyl(6-(2-morpholino-4-oxo-4H-chromen-8-yl)dibenzo[b,d]thiophen-2-yl)carbamate (70.0 mg, 34.9 %) as a white solid.
Sources & evidence
- ORD record
- ord-259872fd14244b3c874c12524fba3d75
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Linked notes
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