3-Bromo-4-pyridinol
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3-Bromo-4-pyridinol
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CAS No:
36953-41-0
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Formula:
C5H4BrNO
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Chemical Name:
3-Bromo-4-pyridinol
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Synonyms:
4-Pyridinol,3-bromo-;3-Bromo-4-pyridinol;3-Bromo-4-hydroxypyridine;3-Bromo-1H-pyridin-4-one
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CAS No:
3-Bromo-4-pyridinol Use and Manufacturing
Step 36-2.; To a solution of T96-2 (8.0 g, 31.3 mmol) in THF (307 mL) at -90° C. was added slowly a solution of n-BuLi (1.15 M in hexanes, 71 mL). The mixture was stirred for 40 min, then water (10 eq) was added and the mixture warmed to room temperature. The solvent was removed under reduced pressure and the resulting residue purified by flash chromatography (acetone:MeOH, 10:1) to give 3.22 g (60percent) of T 96-3.Concentrated sulfuric acid (85.0mL) and the 3-bromo-4-aminopyridine (113.0g, 0.65mol) were added successively to the distilled water (550.0mL) at 0°C, and then NaNOStep 36-2.; To a solution of T96-2 (8.0 g, 31.3 mmol) in THF (307 mL) at -90 C. was added slowly a solution of n-BuLi (1.15 M in hexanes, 71 mL). The mixture was stirred for 40 min, then water (10 eq) was added and the mixture warmed to room temperature. The solvent was removed under reduced pressure and the resulting residue purified by flash chromatography (acetone:MeOH, 10:1) to give 3.22 g (60%) of T 96-3.To a stirred solution of 3, 5-dibromopyridin-4-ol (IN-11; 2.5 g, 0.00988 mol) in dry tetrahydrofuran (100 mL) at -100 C was added 1.6 M t-butyl lithium in hexane (15.6 mL, 0.0247 mol) drop wise under nitrogen atmosphere and stirred for 2 h at -100 C. The reaction mixture was quenched with water (1.77 g, 0.0988 mol) at -100 C and allows the reaction mixture to RT slowly. The reaction mixture was evaporated. The obtained crude was purified with silica gel chromatography by 0 -12% methanol in dichloromethane to afford the title compound. 1H NMR (400 MHz, DMSO-i¾) delta: 11.71 (s, 1 H), 8.15 (s, 1 H), 7.66-7.65 (d, J= 5.6 Hz, 1 H), 6.20-6.18 (d, J=6.4 Hz, 1 H). MS (M+l): 173.8
Computed Properties
Molecular Weight:174.00
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:172.94763
Monoisotopic Mass:172.94763
Topological Polar Surface Area:29.1
Heavy Atom Count:8
Complexity:171
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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