2-Bromo-5-trifluoromethoxypyridine
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2-Bromo-5-trifluoromethoxypyridine
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CAS No:
888327-36-4
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Formula:
C6H3BrF3NO
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Chemical Name:
2-Bromo-5-trifluoromethoxypyridine
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Synonyms:
2-Bromo-5-(trifluoromethoxy)pyridine;2-BROMO-5-TRIFLUOROMETHOXYPYRIDINE;MFCD10698596;Pyridine, 2-bromo-5-(trifluoromethoxy)-;2-bromo-5-trifluoromethoxy-pyridine;SCHEMBL1472705;CTK5G1933;DTXSID70671908;KS-00000HG0;4644AC
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CAS No:
Characteristics
22.1
3.1
1.737 g/cm3
194.1°C at 760 mmHg
71.2ºC
H2O: Slightly soluble (1.6 g/L) (25 ºC)
Safety Information
Ⅲ
6.1
2810
43
36/37
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Bromo-5-trifluoromethoxypyridine Use and Manufacturing
2-Bromo-5-trifluoromethoxy pyridine (31); A solution of 2-chloro-5-trifluoromethoxy pyridine (6, 7.0 g, 35.4 mmol) and bromotrimethylsilane (10.8 g, 9.3 mL, 70.8 mmol, 2 eq) in propionitrile (35 mL) was heated under reflux for 24 h. GC monitoring indicated 100percent conversion. The mixture was distilled in vacuum to afford pure 2-bromo-4-trifluoromethoxy pyridine (31, 7.0 g, 28.7 mmol, 81percent) as a colorless oil; b.p. 63-66 Step 2; 2-Bromo-5-trifluoromethoxy-pyridine:; Into a 50 mL sealed tube was placed 6-bromopyridin-3-ol (2.5 g, 14.37 mmol), perchloromethane (6.6 g, 42.86 mmol) and antimony pentafloride (101 g, 465.44 mmol). The resulting solution was heated at 1502-Bromo-5-trifluoromethoxy pyridine (31); A solution of 2-chloro-5-trifluoromethoxy pyridine (6, 7.0 g, 35.4 mmol) and bromotrimethylsilane (10.8 g, 9.3 mL, 70.8 mmol, 2 eq) in propionitrile (35 mL) was heated under reflux for 24 h. GC monitoring indicated 100percent conversion. The mixture was distilled in vacuum to afford pure 2-bromo-4-trifluoromethoxy pyridine (31, 7.0 g, 28.7 mmol, 81percent) as a colorless oil; b.p. 63-66 Step 2; 2-Bromo-5-trifluoromethoxy-pyridine:; Into a 50 mL sealed tube was placed 6-bromopyridin-3-ol (2.5 g, 14.37 mmol), perchloromethane (6.6 g, 42.86 mmol) and antimony pentafloride (101 g, 465.44 mmol). The resulting solution was heated at 150To a mixture of NaH (60% dispersion in mineral oil, 22.7 mg, 0.57 mmol) in DMF (0.84 mL) at 0 C were added intermediate 116 (50.0 mg, 0.19 mmol) and 15 -crown-5 (37.8 pL, 0.23 mmol). Then A solution of 33.1 2-bromo-5-(trifluoromethoxy)pyridin-1-ium-1-olate Commercially available Example 277A: (E) -ethyl 3-(5-(trifluoromethoxy)pyridin-2-yl)acrylate (1585) Dimethoxy ethane (5 mL) and water (0.1 mL) were added to a mixture of (E)-ethyl 3- (4, 4, 5, 5-tetramethyl-l , 3, 2-dioxaborolan-2-yl)acrylate (Frontier, 0.684 g, 3.02 mmol), potassium carbonate (0.87 g, 6.30 mmol), [l, -bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.21 g, 0.25 mmol) and Dimethoxyethane (5 mL) and water (0.1 mL) were added to a mixture of (£T)-ethyl 3- (4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)acrylate (Frontier, 0.684 g, 3.02 mmol), potassium carbonate (0.87 g, 6.30 mmol), [l, l'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)(0.21 g, 0.25 mmol) and Step 10B: N-[2-(l -benzylpiperidin-4-yl)ethyll -l -[5-(trifluoromethoxy)pyridin-2- yl]piperidine-4-carboxamide (0605) To a solution of 10b (20 mg, 0.06 mmol, 1.0 eq) and 2-bromo-5- (trifluoromethoxy)pyridine (14 mg, 0.06 mmol, 1.0 eq) in toluene (1 mL) was added sodium tert-butoxide (17 mg, 0.18 mmol, 3.0 eq), racemic 2, 2'-bis(diphenylphosphino)- Iota , Gamma-binaphthyl (3.7 mg, 0.006 mmol, 0.10 eq), and lastly tris(dibenzylideneacetone)- dipalladium(O) (5.5 mg, 0.006 mmol, 0.10 eq), and the reaction mixture stirred vigorously at 100 C overnight. The resulting dark suspension was cooled, passed through an HPLC filter and concentrated. Then, the crude material was treated with 1.5 mL of MeOH, passed through an additional HPLC filter (leaving any precipitate behind), and submitted for directly for preparative chromatography yielding N-[2-(l - benzylpiperidin-4-yl)ethyl] -l -[5-(trifluoromethoxy)pyridin-2-yl]piperidine-4- carboxamide 10-1.
Computed Properties
Molecular Weight:241.99
XLogP3:3.1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:240.93501
Monoisotopic Mass:240.93501
Topological Polar Surface Area:22.1
Heavy Atom Count:12
Complexity:152
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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2-Bromo-5-trifluoromethoxypyridine
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