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6th February 2013 @ 06:18
Mnr: MNR91-100

As per compound 3a here

 

 Procedure

A mixture of Ethyl 5-hydroxy-2-methylindole-3-carboxylate (1.00 g, 4.56 mmol), iodobenzene (0.36 mL, 3.19 mmol), CuI (0.13 g, 0.68 mmol) and Cs2CO3 (2.08 g, 6.39 mmol), in DMF (7mL) was stirred at 120 °C under argon for 16 h during which time the reaction turned black.  Water (40 mL) was added and was extracted with EtOAc (30 mL x 3) (there was trouble dissolving some of the crude and it was left behind).  The organic fractions were combined and dried over magnesium sulphate, filtered and concentrated to give a browm oil (still containing DMF)


Column - 30-75% EtOAc/Hex


Fracs 5-17 - higher running new spot - brown solid - 0.147 g

Fracs 19-41 - looks like starting material - 0.319 g

 

Strings


Starting Material

InChI=1S/C12H13NO3/c1-3-16-12(15)11-7(2)13-10-5-4-8(14)6-9(10)11/h4-6,13-14H,3H2,1-2H3

InChI=1S/C6H5I/c7-6-4-2-1-3-5-6/h1-5H

Product

InChI=1S/C18H17NO3/c1-3-22-18(21)17-12(2)19(13-7-5-4-6-8-13)16-10-9-14(20)11-15(16)17/h4-11,20H,3H2,1-2H3

Attached Files
MNR96-1_table.PNG
MNR96_scheme.png
mnr96-1_frac5-17_1H.pdf
mnr96-1_frac19-41_1H.pdf
mnr96-1_frac5-17_13C.pdf
mnr96-1_frac19-41_13C.pdf
mnr96-1_frac19-41.zip
mnr96-1_frac5-17.zip