Tributylphosphine → HCID 22570306, compound

1,1′-(Azodicarbonyl)dipiperidine (0.18 g, 0.7 mmol) was added to a solution of methyl 3-(5-hydoxylindolyl)-2-benzylpropanoate (0.12 g, 0.39 mmol), as prepared in the preceding step, 2-(3-hydroxypropyl)aminopyridine (0.07 g, 0.47 mmol), as prepared instep b of Example 1, and tri-n-butylphosphine (0.14 g, 0.7 mmol) in tetrahydrofuran (6.0 mL). After stirring at ambient temperature overnight (16 h), the reaction was concentrated in vacuo and the residue purified by flash chromatography on silica gel (10%–50% ethyl acetate in hexane) to give the title compound as a yellow oil (0.064 g, 38%). 1H-NMR (400 MHz, CDCl3) δ 8.08 (br s, 1H), 7.40 (m, 1H), 7.37 (m, 1H), 7.22 (m, 2H), 7.00 (m, 3H), 6.84 (dd, J=8.9, 2.4 Hz, 1H), 6.54 (m, 1H), 6.40 (d, J=8.4 Hz, 2H), 6.36 (d, J=3.1 Hz, 1H), 4.77 (br s, 1H), 4.40 (m, 1H), 4.17 (m, 3H), 3.52 (m, 5H), 3.24 (m, 1H), 3.08 (m, 1H), 2.76 (m, 1H), 2.11 (m, 2H).

1. concentrationthe reaction was concentrated in vacuo
2. customthe residue purified by flash chromatography on silica gel (10%–50% ethyl acetate in hexane)

ORD record

ord-ce4e37ec37e9405694a3b538dc143868

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07241789B2