138343-75-6

Basic information

• Product Name: 2-(BOC-AMINO)-3-METHYLPYRIDINE
• Synonyms: (3-METHYLPYRIDINE-2-YL)CARBAMIC ACID TERT-BUTYL ESTER;Carbamic acid, (3-methyl-2-pyridinyl)-;2-tert-butoxycarbonylamino-3-methylpyridine;N-Boc-3-isopropylpyridin-2-amine;N-Boc-3-methylpyridin-2-amine;2-BOC-Amino-3-picoline;t-Butyl 3-methylpyridin-2-ylcarbamate;tert-butyl N-(3-Methylpyridin-2-yl)carbaMate
• CAS NO: 138343-75-6
• Molecular Formula: C₁₁H₁₆N₂O₂
• Molecular Weight: 208.26
• Product Categories: Heterocyclic Compounds;C9 to C46;Heterocyclic Building Blocks;Pyridines;N-BOC;pharmacetical
• Mol File: 138343-75-6.mol
• Article Data: 30

Chemical Properties

• Melting Point: 134-138 °C(lit.)
• Boiling Point: 268.5°Cat760mmHg
• Flash Point: 116.2°C
• Appearance: /
• Density: 1.108g/cm³
• Vapor Pressure: 0.008mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 12.56±0.70(Predicted)
• CAS DataBase Reference: 2-(BOC-AMINO)-3-METHYLPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(BOC-AMINO)-3-METHYLPYRIDINE(138343-75-6)
• EPA Substance Registry System: 2-(BOC-AMINO)-3-METHYLPYRIDINE(138343-75-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 138343-75-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 64, p. 500, 2008 DOI: 10.1016/j.tet.2007.11.011

InChI:InChI=1/C11H16N2O2/c1-8-6-5-7-12-9(8)13-10(14)15-11(2,3)4/h5-7H,1-4H3,(H,12,13,14)

Upstream product

• 1603-40-3 3-methylpyridin-2-ylamine 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 23612-48-8 2-methyl-1H-pyrrolo[2,3-b]pyridine 
• 199296-32-7 2-t-butyloxycarbonylamino-3-methylpyridine-N-oxide 
• 1187323-27-8 N-(1-oxidotetrahydro-2H-thiopyran-4-yl)-4-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]benzenesulfonamide trifluoroacetate 
• 1187323-29-0 N-(1-oxidotetrahydro-2H-thiopyran-4-yl)-4-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]benzenesulfonamide formate 
• 1187323-24-5 N-(tetrahydro-2H-thiopyran-4-yl)-4-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]benzenesulfonamide 
• 271-63-6 7-Azaindole 
• 947017-65-4 2-(thiophen-2-yl)-7-azaindole 
• 70720-38-6 benzyl-(3-methyl-2-pyridinyl)amine 
• 156267-13-9 3-methyl-2-(N-methylamino)pyridine 
• 1445435-83-5 C₁₈H₂₁ClN₂O₂ 
• 1037253-14-7 5-bromo-3-ethylpyridin-2-amine 
• 1313810-55-7 2-[1-(4-cyclopropanesulfonylphenyl)-2-(2,4-difluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine 
• 1313810-39-7 2-[2-cyclopentyl-1-(4-cyclopropanesulfonylphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine 
• 221675-35-0 1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester 

Relevant articles and documents

Iridium- and rhodium-catalyzed dehydrogenative silylations of C(sp 3) - H bonds adjacent to a nitrogen atom using hydrosilanes

Now that is just silylated: In the presence of iridium or rhodium catalysts, C(sp3) - H bonds adjacent to a nitrogen atom were silylated by the aid of a pyridine-directing group. In iridium catalysis, a hydrogen-trapping reagent such as norbornene or tert-butylethylene, which is usually required in late transition-metal-catalyzed dehydrogenative coupling reactions, was not required. In rhodium catalysis, however, 1 equivalent of COD (1,5-cyclooctadiene) was necessary to induce higher conversion. Copyright

Design and synthesis of novel pyrrolo[2,3-b]pyridine derivatives targeting V600EBRAF

Several pyrrolo[2,3-b]pyridine-based B-RAF inhibitors are well known and some of them are currently FDA approved as anticancer agents. Based on the structure of these FDA approved V600EB-RAF inhibitors, two series of pyrrolo[2,3-b]pyridine scaffold were designed and synthesized in attempt to develop new potent V600EB-RAF inhibitors. The 38 synthesized compounds were biologically evaluated for their V600EB-RAF inhibitory effect at single dose (10 μM). Compounds with high percent inhibition were tested to determine their IC50 over V600EB-RAF. Compounds 34e and 35 showed the highest inhibitory effect with IC50 values of 0.085 μM and 0.080 μM, respectively. Headed for excessive biological evaluation, the synthesized derivatives were tested over sixty diverse human cancer cell lines. Only compound 35 emerged as a potent cytotoxic agent against different panel of human cancer cell lines.

Synthesis method of 5-chloro-7-azaindole

The invention provides a synthesis method of 5-chloro-7-azaindole. The synthesis method comprises the following steps: (1) reacting a dilithium initiator and trimethylbromosilane to prepare silicon-containing organic lithium; (2) reacting 2-amino-3-methylpyridine and di-tert-butyl dicarbonate to prepare 2-N-BOC-amino-3-methylpyridine; (3) performing lithiation on the 2-N-BOC-amino-3-methylpyridine through the silicon-containing organic lithium, and performing delithiation activation, cyclization and dehydration to prepare 7-azaindole; (4) performing hydrogenation reduction reaction on the 7-azaindole to generate 2,3-dihydro-7-azaindole; (5) performing chlorination reaction on the 2,3-dihydro-7-azaindole through liquid chlorine to generate 5-chloro-2,3-dihydro-7-azaindole; and (6) performing dehydrogenation reaction on the 5-chloro-2,3-dihydro-7-azaindole to obtain 5-chloro-7-azaindole. The synthesis method provided by the invention has the advantages of mild conditions and high yield.