3-Bromo-5-methyl-4-pyridinamine

7- (2, 4-Dichloro-phenyl)-2-methyl-2H-pyrazolo [4, 3-c] pyridine NH2 Me step 1 Br, 97 97 98 99 Me v step step 1 ) ci ci ci C1 100 101 102 NH2 NAC2STEP 1 To a solution of 4-amino-3-picoline (97, 10 g, 0.092 mmol) and HBr (50 mL) heated to 70° C was added 15percent H202 (16 mL) over a 1 h period. The reaction mixture was stirred for additional h and poured in ice (100 g). The pH of the solution was adjusted to about 5 with 50percent NAOH and the resulting red precipitate was filtered. The pH was raised to about 9 and the resulting white precipitate was collected by filtration to afford 98 (13.5 g, 78percent theory)A sealed tube was charged with 3-bromo-5-methylpyridin-4-amine [97944-43-9] (1.00 g, 4.26 mmol), isopropenylboronic acid pinacol ester [126726-62-3] (1.07 g, 6.34 mmol), Pd(PPh3)4 (507 mg, 0.43 mmol), l, 4-dioxane (10 mL) and NaHCCL (sat., aq., 10 mL). The reaction mixture was stirred under reflux for 16 h, cooled down and diluted with water and DCM until clear phase separation. The aqueous phase was extracted with DCM. The combined organic extracts were dried (MgS04), filtered and concentrated in vacuo to afford 1-112 (1.77 g, 83%, 39% purity) which was sued as such in the next stepA mixture of General procedure: A mixture of 1-38 (350 mg, 1.471 mmol), isoprenylboronic acid pinacol ester [126726- 62-3] (414.632 pL, 2.21 mmol) and Pd(PPh3)4 (169.937 mg, 0.15 mmol) in NaEC03 sat. solution (2 mL) and l, 4-dioxane (3.76 mL, 44.1 mmol) was stirred and heated under nitrogen atmosphere for 15 min at 130 C in a MW. The mixture was treated with sat. NaHC03 and extracted with EtOAc. The organic layer was separated, dried (MgS04), filtered and the solvents were evaporated in vacuo. The product was purified flash column chromatography (silica, heptane/EtOAc, gradient from 100/0 to 50/50) to obtain 1-39 (205 mg, 92%) as a colourless oil.

Molecular Weight:187.04
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:185.97926
Monoisotopic Mass:185.97926
Topological Polar Surface Area:38.9
Heavy Atom Count:9
Complexity:97.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes