Cc1csc(N)n1.O=C(O)c1cccc(Br)n1>CC(C)(C)[O-].CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd]>Cc1csc(Nc2cccc(C(=O)O)n2)n1
_The aim of this reaction is to synthesize material to check some ideas for route development and see if 'normal' Buchwald conditions is applicable here. IPC.s were taken and the reaction was monitored either by LCMS or HNMR (a crude sample dissolved in DMSO)._ 19/11-2015 14:00 A dried 250 mL rb-flask under nitrogen atmosphere was charged with 4-methylthiazol-2-amine (C0033995, BT250061) (6.61 g, 57.92 mmol), 6-bromopicolinic acid (C0013377, BT249846) (11.7 g, 57.92 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (C0007769, BT234652) (1.326 g, 1.45 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphane (C0018897, BT153355) (2.76 g, 5.79 mmol), SODIUM T-BUTOXIDE (C0006296, BT235115) (16.70 g, 173.76 mmol), Toluene (193 ml) was added and the suspension was heated and stirred at reflux (110 °C). Start heating 14:30 - IPC was taken after 18 h **IPC1 LCMS** , seems difficult to identify if any of the desired product was formed. Made an aqueous wash between citric acid/water and ethyl acetate, tedious separation, analysed the two phases IPC2 LCMS but still impossible to identify any product neither in the organic phase IPC3 LCMS. **No evidence of product formation.** The phases were discarded and the reaction judged as failed
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