1-(1-BROMONAPHTHALEN-4-YL)ETHANONE

A solution of 1-Bromo-naphthalene (10 g, 48.3 mmol) and acetyl chloride (4.2 ml, 58 mmol) in 1, 2-dichloroethane (100 ml) was cooled to 0°C and aluminum chloride (14.4 g, 108 mmol) was added portion wise. The mixture was stirred at RT for 24 hours. The reaction mixture was poured into ice-water (100 ml). The two layers were separated and the water layer was extracted with diethyl ether (3 x 150 ml). The combined organic layers were dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure to give an orange colored oil. The 1- (4-bromo-naphtalen-1-yl)-ethanone was purified by flash chromatography (cyclohexane/ethylacetate: 95/5), yielding an yellow oil (91percent yield). The 1- (4-bromo-naphtalen-1-yl)-ethanone oxime was prepared according to the procedure described for Compound 22, yielding a white powder (98percent yield). Activated zinc dust (24.7 g, 379 mmol) was added portion wise to a suspension of the oxime (10.0 g, 37.9 mmol) in acetic acid (40 ml). The mixture was stirred at RT for 2 hours. The zinc dust was removed by filtration and acetic acid was removed under reduced pressure. Water (100 ml) was added and the pH was adjusted to pH = 13 with 1N NaOH. The water layer was extracted with EtOAc (3 x 100 ml). The combined organic layers were dried over MgS04, filtered and the solvent was removed under reduced pressure, yielding a yellow oil (70percent yield). Boc20 (7.1 g, 31.8 mmol) was added to a solution of the amine (6.6 g, 26.5 mmol) in 1, 4-dioxane (50 ml). The reaction mixture was stirred at RT for 2 hours. The solvent was removed under reduced pressure and the product was purified by flash chromatography (cyclohexane/EtOAc: 95/5), yielding a yellow powder (75percent yield). The bromide (350 mg, 1 mmol) was dissolved in THF (13 ml) /water (2 ml). Potassium acetate (100 mg, 1 mmol), 1, 3-bis-diphenylphosphinopropane (9.0 mg, 0.02 mmol) and palladium- (11)-acetate (9.0 mg, 0.04 mmol) were added. The mixture was stirred at 50 atm CO pressure and 150°C for 3 hours. The reaction mixture was filtered, the filtrate dried over MgS04 and the solvent was removed under reduced pressure to give a yellow- greenish oil (300 mg). The 4- (l-tert-butoxycarbonylamino-ethyl)-naphthalene-l- carboxylic acid was purified by flash chromatography (DCM/MeOH : 90/10), yielding a white powder (14percent yield). The title product was prepared according to the procedure of Compound 31, starting from 4- (1-tert-butoxycarbonylamino-ethyl)-naphthalene-1-carboxylic acid (44 mg) and 4-amino-pyridine (67percent yield).'H NMR (300 MHz, , DMSO-d6): 1.64 ppm (d, 3H, J = 6.6 Hz); 5.3 ppm (q, 1H, J = 6.5 Hz), 7.71 ppm (m, 1H), 8.00 ppm (d, 1H, J = 7.7 Hz), 8.32 ppm (m, 1H), 8. 35 ppm (d, 1H, J = 7.3 Hz), 8.81 ppm (d, 2H, J = 7.2 Hz), 12.2 ppm (s, 1H).Section IExample I-IPreparation of Compound 301 and 302General Procedure I-AA solution of 1-Bromo-naphthalene (I-Ia; 2 g, 9.6 mmol) and acetyl chloride (0.84 mL, 11.6 mmol) in 1, 2-dichloroethane (30 mL) was cooled to 0° C. and aluminum chloride (2.88 g, 21.6 mmol) was added portion wise. The mixture was stirred at r.t. for 24 hours. The reaction mixture was poured into ice-water (100 mL). The two layers were separated and the aqueous layer was extracted with EtOAc (150 mL.x.3). The combined organic layers were dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure to give compound I-Ib as an orange oil (2.16 g, yield 91percent). To a stirred solution of 1.00 g (4.8 mmol) of 1-bromonaphthalene in 15 mL of carbon disulfide at 0 °C in a flame-dried flask under NGeneral procedure: Caution. tert-Butyl hydroperoxide is an exceptionally dangerous chemical that is highly reactive, flammable, and toxic. It is corrosive to skin and mucous membranes and causes respiratory distress when inhaled. A solution of secondary alcohol (1 mmol) and 70percent TBHP (6 or 10 equiv.) was stirred at 100 °C for 24 h. The reaction mixture was quenched with the saturated solution of sodium thiosulfate (5 mL) and extracted with dichloromethane (3 x 10 mL). The combined dichloromethane extracts were dried over anhydrous Na

Molecular Weight:249.10
XLogP3:3.5
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:247.98368
Monoisotopic Mass:247.98368
Topological Polar Surface Area:17.1
Heavy Atom Count:14
Complexity:226
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes