Methyl 5-bromo-2-chloronicotinate
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Methyl 5-bromo-2-chloronicotinate
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CAS No:
78686-79-0
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Formula:
C7H5BrClNO2
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Chemical Name:
Methyl 5-bromo-2-chloronicotinate
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Synonyms:
3-Pyridinecarboxylic acid,5-bromo-2-chloro-,methyl ester;Methyl 2-chloro-5-bromo-3-pyridinecarboxylate;5-Bromo-2-chloronicotinic acid methyl ester;Methyl 5-bromo-2-chloronicotinate;5-Bromo-2-chloropyridine-3-carboxylic acid methyl ester;Methyl 5-bromo-2-chloropyridine-3-carboxylate
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CAS No:
Characteristics
39.2
2.4
Solid
1.7±0.1 g/cm3
48-49 °C @ Solvent: Ethanol, Water
275.6ºC at 760 mmHg
>110 °C
1.569
Safety Information
IRRITANT
NONH for all modes of transport
3
22
Xi,Xn
P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P501
H302
|Warning|H302 (95.12%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 41 companies from 4 notifications to the ECHA C&L Inventory.
Methyl 5-bromo-2-chloronicotinate Use and Manufacturing
To 0.5 L flask charged with 5-Bromo-2-chloronicotinic acid (25.0 g, 106.4 mmol) in MeOH (250 mL) was added HSulfuric acid (2 mL, 52.1 mmol) was added to the suspension of 5-bromo-2-chloronicotinic acid (1) (12.3 g, 52 mmol) was in methanol (100 mL). The mixture was stirred and refluxed for 15 hours. The solvent was evaporated and the residue was neutralized with saturated aqueous NaHC03(aq.). The result suspension was filtered and the solid was washed by water and dried by pump. Methyl 5-bromo-2-chloronicotinate (2) (11.6 g, 89 percent yield) was afforded. NMR (400 MHz, CDCL) δ 8.53 (d, J = 2.4 Hz, 1H), 8.25 (d, J = 2.4 Hz, 1H), 3.93 (s, 3H). To a solution of 5-bromo-2-chloronicotinic acid (50 g, 211 mmol) in MeOH (200 mL) was added H2SO4 (20.7 g, 211.46 mmol) at 25 °C. The mixture heated to 90 °C and stirred for 12 hours. LCMS showed that the reaction was complete. The reaction was neutralized with Na2CO3 to pH = 7-8 and concentrated under reduced pressure to remove MeOH. The residue was extracted with EtOAc (300 mL x 3). The combined organic layer was concentrated under reduced pressure to give methyl 5-bromo-2-chloronicotinate (45 g, 180 mmol, 85percent yield) as a brown solid. ESI-MS (m/z): 249.9 (M+H)+Example 18; 2-(4-(1H-Pyrrolo[2, 3-b]pyridin-4-yloxy)-3-fluorophenylamino)-5-bromo-N-(2, 4-difluorophenyl)nicotinamide, dihydrochloride salt; A) Methyl 5-bromo-2-chloronicotinate; To a suspension of 5-bromo-2-hydroxynicotinic acid (4.34 g, 20 mmol) in 20 mL of SOClPOCl3 (50 mL) was added slowly through an addition funnel to ice-cooled 5-bromo- 2-hydroxynicotinic acid (10 g, 45.9 mmol). The reaction mixture was heated to 95°C and stirred at the same temperature for 16 hr. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure to remove POCh. To the residue was added toluene (100ml), and the mixture evaporated under reduced pressure to remove residual POCb . The obtained residue was diluted with DCM (100 mL) and cooled. MeOH (50 mL) was added slowly through an addition funnel to the mixture under nitrogen. The resulting mixture was then stirred at room temperature for 2 hr. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue thus obtained was diluted with water, neutralized by using saturated aq.NaExample 30 - Preparation of Intermediate 7 [ 00261] The synthesis of Intermediate 7 followed General Procedure 8 following. General Procedure 8 Intermediate 5 Intermediate 7 [ 00262 ] To a round-bottomed flask charged with methyl 5-bromo-2-oxo- l, 2-dihydropyridine-3-carboxylate (Intermediate 5, 50.0 g, 0.2154 mol, 1.0 eq) at 0 C under NExample 24; A. Methyl 5-bromo-2-chloropyridine-3-carboxylate; To a solution of S-bromo-l-chloropyridine-S-carboxylic acid (1.0 g, 4.2 mmol) in methanol :benzene (1 :1, 50 mL) was added trimethylsilyldiazomethane (3.2 mL, 6.5 mmol) at 0
Computed Properties
Molecular Weight:250.48
XLogP3:2.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:248.91922
Monoisotopic Mass:248.91922
Topological Polar Surface Area:39.2
Heavy Atom Count:12
Complexity:179
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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Methyl 5-bromo-2-chloronicotinate
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