1-BOC-6-AMINOINDOLE

White to pale yellow solid

To a 25-mL round-bottom flask was placed a solution of 2-[3-(3- methoxyphenyl)-6-oxo-l, 6-dihydropyridazin-l-yl]propanoic acid (200 mg, 0.73 mmol, as prepared in the previous step) in DMF (5 mL) then tert-butyl 6-amino-lH-indole-l-carboxylate (250 mg, 1.08 mmol), HATU (418 mg, 1.10 mmol), and DIEA (284 mg, 2.20 mmol) were added. The reaction was stirred for 16 h at rt, diluted with EtOAc (50 mL), washed with water (2x50 mL) and brine (1x50 mL), dried over anhydrous Na2S04, and concentrated under reduced pressure. The residue was purified by column chromatography eluting with EtOAc/petroleum ether (1: 10 up to 1: 1) affording 295 mg (83percent) of the title compound as a yellow solid. Mass Spectrum (LCMS, ESI pos): Calcd. for C27H29N405+: 489.2 (M+H); Found: 489.2.Part A. To tert-butyl-6-nitro-1H-indole-1-carboxylate (3.80 g, 14 mmol), prepared according to Part F of using 6-nitro-1H-indole as starting material, was added 150 mL of MeOH and 150 mL of EtOAc. The solution was covered with a stream of N2, and 10 wt percent Pd/C (100 mg) was added in one portion. The mixture was subjected to a hydrogen atmosphere (50 psi) for 14 h and was then filtered and concentrated. Analysis (LC/MS) of the resulting brown residue (3.34 g, 100percent) showed it to be a 20:80 mixture of tert-butyl 6-amino-1-indolinecarboxylate: A solution of the crude anhydride (450 mg, 0.972 mmol) in THF (5 mL) at -78° C. was treated with the magnesium salt of C N-(1-Boc-6-indolyl)-2-nitrobenzamide By methods substantially equivalent to those described in Example 1-C, N-(1-Boc-6-indolyl)-2-nitrobenzamide (2.2 g, 95percent) was prepared from

Molecular Weight:232.28
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:232.121177757
Monoisotopic Mass:232.121177757
Topological Polar Surface Area:57.2
Heavy Atom Count:17
Complexity:298
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes