tert-Butyl carbamate → tert-butyl N-[1-(pyridin-3-ylmethyl)indol-6-yl]carbamate
Reaction equation
Brc1ccc2ccn(Cc3cccnc3)c2c1.CC(C)(C)OC(N)=O>C1COCCO1.CC(=O)O.CC(=O)O.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>CC(C)(C)OC(=O)Nc1ccc2ccn(Cc3cccnc3)c2c1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 110 °C
Procedure
6-bromo-1-(pyridin-3-ylmethyl)-1H-indole (1.3 g, 4.53 mmol), cesium carbonate (2.213 g, 6.79 mmol), tert-butyl carbamate (0.796 g, 6.79 mmol), dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.453 g, 0.95 mmol) and PALLADIUM(II) ACETATE (0.071 g, 0.32 mmol) were placed under a nitrogen atmosphere. dry degassed dioxane (20 mL) was added and the reaction was warmed to 110 °C (using microwave). After reaction completion (3h) the the reaction was diluted with EtOAc(20mL) and water (10mL) and the organic layer was separated. The aqueous layer was washed with a further portion of EtOAc(10mL) and the combined organic layers were dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 30 to 70% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford tert-butyl 1-(pyridin-3-ylmethyl)-1H-indol-6-ylcarbamate (1.200 g, 82 %) as a colourless gum.
Sources & evidence
- ORD record
- ord-2ea0e4e929e149198feaa40dbd6f469f
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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