TERT-BUTYL (5-FORMYLPYRIDIN-2-YL)CARBAMATE

6.0 g (21 .3 mmol) of (5-Bromo-pyridin-2-yl)-carbamic acid tert-butyl ester was dissolved in THF (55 mL). A solution of 4.9 mL (32 mmol) TMEDA, 241 mg (0.64 mmol)CataCxium A, and 48 mg (0.213 mmol) Pd(OAc)To a solution of (5-Bromo-pyridin-2-yl)-carbamic acid tert-butyl ester (1.0 g, 3.7 mmol, 1.0 equiv.) in dry THF (12 mL) at 0 C was added a2 M solution of i-PrMgCl in THF (1.85 mL, 3.7 mmol, 1.0 equiv.) during 5 min. The clear solution wasstirred at that temperature for an additional 5 min, and a 2.5 M solution of n-BuLi in hexanes (3 mL, 7.5 mmol, 2.0 equiv.) was added dropwise during 5 min, while maintaining the temperature below20 C. The resulting mixture was stirred at that temperature for 0.5 h, dry DMF (0.27 g, 3.7 mmol, 1.0 equiv.) in dry THF (5 mL) was added dropwise during 10 min. The resulting mixture was warmedto 20 C in 0.5 h and quenched with water (6 mL). After stirring the mixture below 20 C for 10 min, the phases were separated and the water phase was extracted one additional time with ethyl acetate.The resulting suspension was allowed to reach room temperature and fitered through a 0.5 1 cmpad of silica gel eluted with 10 mL of ethyl acetate. The ®ltrate was concentrated and the residue waspuri®ed by ash chromatography on silica gel (eluent: petroleum ether/ethyl acetate = 10:1) to affordproduct 3a as white solid, 0.73 g (yield: 90percent). 1H-NMR (600 MHz, DMSO) 10.42 (s, 1H), 9.94 (s, 1H), 8.93–8.60 (m, 1H), 8.17 (dd, J = 8.8, 2.3 Hz, 1H), 7.99 (d, J = 8.8 Hz, 1H), 1.48 (s, 9H). 13C-NMR (151 MHz, DMSO) 191.18, 157.08, 152.82, 152.40, 138.23, 127.30, 112.23, 80.97, 28.37.To a stirring solution of (Boc)20 (1.75 g, 8 mmol) in DCM (10 mL)was added the suspension of 6-aminonicotinaldehyde SM 1 (488 mg, 4 mmol), DMAP (25 mg, 0.2 mmol) and Et3N(1.2 g, 12 mmol) in DCM (20 mL) at RT and stirred overnight. The reaction mixture was concentrated and the residue was diluted with H20 and extracted with DCM. Combined organicextracts were dried over anhydrous Na2504 and concentrated under reduced pressure to obtain cmde product, which was purified by silica gel column chromatography eluting with 50percent EtOAc in PE to afford compound 1(1.2 g, 93percent) as white solid. LC-MS: m/z = 123.0 [M+H-BOC]

Molecular Weight:222.24
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:222.10044231
Monoisotopic Mass:222.10044231
Topological Polar Surface Area:68.3
Heavy Atom Count:16
Complexity:260
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes