Ethanone, 1-(5-hydroxy-2-pyridinyl)- (9CI)

General procedure: (R)-3-(4-Hydroxy-phenoxy)-pyrrolidin-2-one (Typical Procedure 7) A mixture of (R)-3-(4-benzyloxy-phenoxy)-pyrrolidin-2-one (61 g), MeOH/DCM (2:1, 2 L) and Pd (10% on carbon, 6 g) was shaken under an atmosphere of hydrogen for 20 hours. The catalyst was removed by filtration and the filtrate concentrated to provide the subtitle compound. MS ESI+: m/z=194 [M+H]+.General procedure: A mixture of (R)-3-(4-benzyloxy-phenoxy)-pyrrolidin-2-one (61 g), MeOH/DCM (2:1 , 2 L) and Pd (10% on carbon, 6 g) was shaken under an atmosphere of hydrogen for 20 hours. The catalyst was removed by filtration and the filtrate concentrated to provide the subtitle compound.K2CO3 (504 mg, 3.65 mmol) followed benzylbromide (0.22 mL, 1.82 mmol) was added to a solution of Example 164 2-(4-chloro-3-fluorophenoxy)-iV-[3-(2-{ [6-(l-hydroxyethyl)pyridin-3- yl] oxy }acetamido)bicyclo [ 1.1.1] pentan- 1-yl] acetamide (Compound 263) A mixture of Example 28A (0.1 g, 0.235 mmol), 1 -(5 -hydroxy pyridin-2-yl)ethanone (0.065 g, 0.471 mmol), potassium carbonate (0.065 g, 0.471 mmol) and potassium iodide (2.73 mg, 0.016 mmol) in acetone (2.0 mL) was stirred at 140 C (0-450 W) in a Biotage Initiator microwave reactor for 45 minutes. The suspension was filtered, and the filtrate was concentrated. This residue and NaBH4 (0.089 g, 2.35 mmol) in methanol was stirred at ambient temperature overnight. The reaction mixture was concentrated, and the residue was purified by HPLC (10-85% acetonitrile in 0.1% trifluoroacetic acid/water at 25 rnL/minute on a Phenomenex Luna C18 5 muiotaeta 100 A AXIA column (250 mm chi 21.2 mm)) to give 59 mg of the title compound as a white solid. XH NMR (400 MHz, DMSO-c) delta ppm 8.74 (d, J = 26.6 Hz, 2H), 8.30 (d, J = 2.8 Hz, 1H), 7.81 - 7.60 (m, 2H), 7.47 (t, J = 8.9 Hz, 1H), 7.05 (dd, J = 11.4, 2.8 Hz, 1H), 6.83 (ddd, J = 9.0, 2.9, 1.2 Hz, 1H), 4.85 (q, J = 6.5 Hz, 1H), 4.61 (s, 2H), 4.46 (s, 2H), 2.25 (s, 6H), 1.37 (d, J = 6.5 Hz, 3H). MS (ESI+) m/z 464.0 (M+H)+.A mixture of Example 28A (0.1 g, 0.235 mmol), l-(5-hydroxypyridin-2-yl)ethanone (0.065 g, 0.471 mmol), potassium carbonate (0.065 g, 0.471 mmol) and potassium iodide (2.73 mg, 0.016 mmol) in acetone (2.0 mL) was stirred at 140 C (0-450 W) in a Biotage Initiator microwave reactor for 45 minutes. The suspension was filtered, and the filtrate was concentrated. This residue and NaBH^ (0.089 g, 2.35 mmol) in methanol was stirred at ambient temperature overnight. The reaction mixture was concentrated, and the residue was purified by HPLC (10-85% acetonitrile in 0.1% trifluoroacetic acid/water at 25 mL/minute on aPhenomenex Luna CI 8 5 mupiiota 100 A AXIA column (250 mm x 21.2 mm)) to give 59 mg of the title compound as a white solid.JH NMR (400 MHz, DMSO-

Molecular Weight:137.14
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:137.047678466
Monoisotopic Mass:137.047678466
Topological Polar Surface Area:50.2
Heavy Atom Count:10
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes