5-Bromo-2-methoxy-3-pyridinecarboxylic acid
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5-Bromo-2-methoxy-3-pyridinecarboxylic acid
structure -
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CAS No:
54916-66-4
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Formula:
C7H6BrNO3
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Chemical Name:
5-Bromo-2-methoxy-3-pyridinecarboxylic acid
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Synonyms:
3-Pyridinecarboxylic acid,5-bromo-2-methoxy-;5-Bromo-2-methoxy-3-pyridinecarboxylic acid;5-Bromo-2-methoxynicotinic acid
- Categories:
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CAS No:
5-Bromo-2-methoxy-3-pyridinecarboxylic acid Basic Attributes
232.03
232.03
DTXSID20559520
2933399090
Safety Information
IRRITANT
NONH for all modes of transport
nwg
24/25
Xi
Irritant/Keep Cold
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 6 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
5-Bromo-2-methoxy-3-pyridinecarboxylic acid Use and Manufacturing
To a solution of 2-methoxynicotinic acid (20 g, 130.60 mmol) in H20 (1500 mL), Br2 (20 mL, 375.45 mmol) was added at room temperature. The mixture was stirred at room temperature overnight. The reaction mixture was filtered, washed with water and dried to provide 5-bromo-2-methoxynicotinic acid (25 g, yield: 82percent). 1H- MR (DMSO, 400 MHz) δ 13.33 (br s, 1H), 8.47 (d, J= 2.4 Hz, 1H), 8.21 (d, J= 2.4 Hz, 1H), 3.90 (s, 3H). MS (M+H)+: 232 / 234.Step 1-Synthesis of 5-bromo-2-methoxynicotinic acid General procedure: 6 -(Dimethylamino)-lH-indole-2-carboxylic acid (0.02 g, 1 eq., 0.12 mmol), HATU (0.05 g, 1.1 eq., 0.13 mmol) and DIPEA (0.04 mL, 2 eq., 0.24 mmol) were dissolved in DMF (2 mL) and stirred at room temperature for 10 min. 2, 3, 4, 5-Tetrahydro- IH-pyrido [ 4, 3-b] indole (0.03 g, 1 eq., 0.12 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. The reaction was quenched with 2M aq. HC1(10 mL) and the aqueous phase was extracted with EtOAc (2 c 10 mL) . The combined extracts were washed sequentially with water (15 mL) and brine (15 mL) , dried over Na2SC>4, filtered and concentrated in vacuo to afford the crude product. The title compound was obtained after preparative LC-MS, as a white solid (0.01 g, 34%).To a suspension of 5-Bromo-2-methoxy-pyridine-3 -carboxylic acid (162 mg, 0.70 mmol) and 6-[4-[(lS)- 2, 2, 2-trifluoro-l-methyl-ethyl]-l, 2, 4-triazol-3-yl]pyridin-2-amine (180 mg, 0.70 mmol) were dissolved in triethylamine (1.1 mL, 7.78 mmol). Propylphosphonic anhydride (> 50 wt % in EtOAc, 0.70 mL) was added and the stirred reaction mixture was heated at 80 C for 3 h. The reaction was cooled to rt and quenched by addition of MeOH (5 mL). The resulting solid was filtered and evaporated in vacuo to give the title compound (130 mg, 39%) as a white solid. 1H NMR (400 MHz, CD3OD) d 9.01 (s, 1H), 8.45 (br d, 7=5.52 Hz, 2H), 8.38 (br d, 7=7.78 Hz, 1H), 7.95 - 8.09 (m, 2H), 6.91 (td, 7=7.34, 14.43 Hz, 1H), 4.14 (s, 3H), 1.88 (d, 7=7.03 Hz, 3H). MS (ESI): 471.0 [(M + H) (79Br)]+.A mixture of
Computed Properties
Molecular Weight:232.03
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:230.95311
Monoisotopic Mass:230.95311
Topological Polar Surface Area:59.4
Heavy Atom Count:12
Complexity:176
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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5-Bromo-2-methoxy-3-pyridinecarboxylic acid
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