4-Bromo-2-fluoropyridine-3-carboxaldehyde

A mixture of 4-bromo-2-fluoro- pyridine-3-carbaldehyde (2.04 g, 10.0 mmol, 1.0 eq.), methylhydrazine (1.05 mL, 20.0 mmol, 2.0 eq.) and DIEA (3.48 mL, 20.0 mmol, 2.0 eq.) in MeCN (50 mL, 0.2 M) was stirred at 50 C. After 1 h, the mixture was diluted with EtOAc and washed with water (2x). The aqueous layer was extracted with EtOAc (3x). The combined extracts were washed with brine, dried over Na2S04, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel (0-60% EtOAc/hexanes) afforded the title compound as a white crystalline solid (1.73 g, 82%). XH NMR (400 MHz, CDCI3) delta 8.36 (d, J= 4.9 Hz, 1H), 8.04 (s, 1H), 7.33 (d, J = 4.9 Hz, 1H), 4.18 (s, 3H); ES-MS [M+l]+: 214.2.To a solution of ethyl prop-2-ynoate (2.92 g, 29.8 mmol) in THF (100 mL) at -78 C under N2was added LDA (14.9 mL of a 2M solution in THF/heptane/ethylbenzene, 29.8 mmol) dropwise. The mixture was stirred at -78 C for 20 minutes and a solution of

Molecular Weight:204.00
XLogP3:1.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:202.93820
Monoisotopic Mass:202.93820
Topological Polar Surface Area:30
Heavy Atom Count:10
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes