Home Cart 0 Sign in  

[ CAS No. 3510-66-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 3510-66-5
Chemical Structure| 3510-66-5
Structure of 3510-66-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 3510-66-5 ]

Related Doc. of [ 3510-66-5 ]

Alternatived Products of [ 3510-66-5 ]

Product Details of [ 3510-66-5 ]

CAS No. :3510-66-5 MDL No. :MFCD00209553
Formula : C6H6BrN Boiling Point : -
Linear Structure Formula :- InChI Key :YWNJQQNBJQUKME-UHFFFAOYSA-N
M.W : 172.02 Pubchem ID :564216
Synonyms :

Calculated chemistry of [ 3510-66-5 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.9
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 2.39
Log Po/w (WLOGP) : 2.15
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 2.54
Consensus Log Po/w : 2.12

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.97
Solubility : 0.186 mg/ml ; 0.00108 mol/l
Class : Soluble
Log S (Ali) : -2.3
Solubility : 0.858 mg/ml ; 0.00499 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.26
Solubility : 0.0948 mg/ml ; 0.000551 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.6

Safety of [ 3510-66-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3510-66-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 3510-66-5 ]
  • Downstream synthetic route of [ 3510-66-5 ]

[ 3510-66-5 ] Synthesis Path-Upstream   1~40

  • 1
  • [ 3510-66-5 ]
  • [ 1603-41-4 ]
YieldReaction ConditionsOperation in experiment
100% With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 120℃; for 16 h; Sealed tube General procedure: A mixture of substrate (0.25 mmol), complex 1 (2.5 × 10− 3 mmol), Cs2CO3 (1 mmol), Conc. NH3(aq) (0.5 mL) and TBAB (0.25 mmol) in water (0.5 mL) were loaded in a sealed reaction tube. The reaction temperature was increased to 110–140 °C and the reaction mixture was stirred for 8–24 h. After cooling to RT, the reaction mixture was poured into a saturated NaCl solution, extracted with ethyl acetate and dried over anhydrous MgSO4. After removal of solvents, the residue was re-crystallized or chromatographed on silica gel. All products were characterized by NMR spectroscopy and were consistent with the literature data.
Reference: [1] Catalysis Communications, 2013, vol. 32, p. 28 - 31
[2] Advanced Synthesis and Catalysis, 2009, vol. 351, # 11-12, p. 1722 - 1726
  • 2
  • [ 1603-41-4 ]
  • [ 3510-66-5 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With hydrogen bromide; bromine In water at -20℃; for 3 h;
Stage #2: at -20℃; for 1 h;
Procedure B Intermediate 7: 2- [[6-MORPHOLIN-4-YL-PYRIDIN-3-YL] ETHANAMINE] Step 1: 2-Bromopicoline To a stirred solution of 2-amino-5-picoline (120g, 1. [10MOL)] in 1. 5L of 48percent HBr was added [160ML] [OF BR2] (498g, 3. [1MOL) AT-20°C] over a period of lh and then allowed to stir at same temperature for 2h. To this mixture was added slowly a solution [OF NAN02] (204g, 2. [95MOL,] in 300mL of water) and the resuting solution was allowed to stir for another lh [AT-20°C.] The reaction mixture was quenched at-20°C by addition of aqueous [NAOH] [(1.] 2Kg of [NAOH] in 2L of water) then extracted with diethyl ether [(3XLL).] The organic layer was washed with water, brine, dried with [NA2SO4] and concentrated to give a crude residue. After purification by distillation (bath temp. [130°C,] vacuum temp. [85-90°C,] vacuum=0. [01MM),] 172g 2-bromopicoline were obtained as off white low melting solid (90percent). [TLC, Rf= 0.8, diethyl ether]
94% With sodium hydroxide; hydrogen bromide; sodium nitrite In water Step 3:
Preparation of 2-bromo-5-picoline.
A solution of 1500 mL (14 mol) of 48percent hydrobromic acid was cooled to 10° C. and 300 g (2.8 mol) of 2-amino-5-picoline (Aldrich) was added slowly.
The solution was maintained at or below 0° C. while 450 mL (8.8 mol) of bromime was added dropwise.
After the bromine addition was complete, a solution of 500 g (7.3 mol) of sodium nitrite in 1000 mL of water was added slowly over 6 h.
The reaction pH was adjusted by the careful addition of 1500 mL (56 mol) of 50percent sodium hydroxide at such a rate that the temperature was maintained below 30° C.
The product precipitated from the nearly colorless reaction mixture; filtration gave 450 g (94percent) of 2-bromo-5-picoline as a yellow powder: mp 38°-40° C.; NMR 7.27 (s, 1H), 7.28 (s, 1H), 7.12 (br s, 1H).
94% With sodium hydroxide; hydrogen bromide; bromine; sodium nitrite In water Step 3:
Preparation of 2-bromo-5-picoline
A solution of 1500 mL (14 mol) of 48percent hydrobromic acid was cooled to 10° C. and 300 g (2.8 mol) of 2-amino-5-picoline (Aldrich) was added slowly.
The solution was maintained at or below 0° C. while 450 mL (8.8 mol) of bromine was added dropwise.
After the bromine addition was complete, a solution of 500 g (7.3 mol) of sodium nitrite in 1000 mL of water was added slowly over 6 h.
The reaction pH was adjusted by the careful addition of 1500 mL (56 mol) of 50percent sodium hydroxide at such a rate that the temperature was maintained below 30° C.
The product precipitated from the nearly colorless reaction mixture; filtration gave 450 g (94percent) of 2-bromo-5-picoline as a yellow powder: mp 38-40° C.; NMR 7.27 (s, 1H), 7.28 (s, 1H), 7.12 (br s, 1H).
94% With sodium hydroxide; hydrogen bromide; bromine; sodium nitrite In water Step 3:
Preparation of 2-bromo-5-picoline.
A solution of 1500 mL (14 mol) of 48percent hydrobromic acid was cooled to 10° C. and 300 g (2.8 mol) of 2-amino-5-picoline (Aldrich) was added slowly.
The solution was maintained at or below 0° C. while 450 mL (8.8 mol) of bromine was added dropwise.
After the bromine addition was complete, a solution of 500 g (7.3 mol) of sodium nitrite in 1000 mL of water was added slowly over 6 h.
The reaction pH was adjusted by the careful addition of 1500 mL (56 mol) of 50percent sodium hydroxide at such a rate that the temperature was maintained below 30° C.
The product precipitated from the nearly colorless reaction mixture; filtration gave 450 g (94percent) of 2-bromo-5-picoline as a yellow powder: mp 38°-40° C.; NMR 7.27 (s, 1 H), 7.28 (s, 1 H), 7.12 (br s, 1 H).
94% With sodium hydroxide; hydrogen bromide; bromine; sodium nitrite In water Step 3:
Preparation of 2-bromo-5-picoline
A solution of 1500 mL (14 mol) of 48percent hydrobromic acid was cooled to 10° C. and 300 g (2.8 mol) of 2-amino-5-picoline (Aldrich) was added slowly.
The solution was maintained at or below 0° C. while 450 mL (8.8 mol) of bromine was added dropwise.
After the bromine addition was complete, a solution of 500. g (7.3 mol) of sodium nitrite in 1000 mL of water was added slowly over 6 h.
The reaction pH was adjusted by the careful addition of 1500 mL (56 mol) of 50percent sodium hydroxide at such a rate that the temperature was maintained below 30° C.
The product precipitated from the nearly colorless reaction mixture; filtration gave 450 g (94percent) of 2-bromo-5-picoline as a yellow powder: mp 38°-40° C.; NMR 7.27 (s, 1H), 7.28 (s, 1H), 7.12 (br s, 1H).

Reference: [1] Synthesis, 1994, # 1, p. 87 - 92
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2002, vol. 177, # 11, p. 2579 - 2587
[3] Patent: WO2003/106455, 2003, A1, . Location in patent: Page 55
[4] Organic Letters, 2000, vol. 2, # 21, p. 3373 - 3376
[5] Tetrahedron Letters, 1998, vol. 39, # 47, p. 8643 - 8644
[6] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14622 - 14626
[7] Chemistry - A European Journal, 2018, vol. 24, # 50, p. 13158 - 13169
[8] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
[9] Journal of the American Chemical Society, 1950, vol. 72, p. 4362
[10] Journal of Organic Chemistry, 1953, vol. 18, p. 598,604
[11] Journal of Organic Chemistry, 1949, vol. 14, p. 509,513
[12] Organic Magnetic Resonance, 1982, vol. 20, # 4, p. 242 - 248
[13] Synthesis, 1999, # 5, p. 779 - 782
[14] Tetrahedron Letters, 2001, vol. 42, # 35, p. 6113 - 6115
[15] Tetrahedron Letters, 2005, vol. 46, # 36, p. 6033 - 6036
[16] Tetrahedron Letters, 2006, vol. 47, # 20, p. 3471 - 3473
[17] Patent: US5861420, 1999, A,
[18] Patent: US6090828, 2000, A,
[19] Patent: US5196537, 1993, A,
[20] Patent: US5451593, 1995, A,
[21] Patent: US4184041, 1980, A,
[22] Patent: US6214878, 2001, B1,
  • 3
  • [ 1603-41-4 ]
  • [ 3510-66-5 ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydroxide; bromine; sodium nitrite In water; hydrogen bromide EXAMPLE 28
3-(4-[5-Methyl-2-pyridyl]piperazin-1-yl)methyl-1H-pyrrolo[2,3-b]pyridine
Bromine (74 g, 24 ml, 0.46 mmol) was added dropwise with vigorous stirring to a solution of 2-amino-5-picoline (20.0 g, 0.19 mol) in 48percent hydrobromic acid (300 ml) at -10° C. Sodium nitrite (32 g, 0.46mol) in water (80 ml) was added dropwise to the orange suspension, maintaining the temperature below -5° C., and the mixture was then stirred at room temperature for 30 minutes.
The mixture was recooled to 0° C. and sodium hydroxide (188 g, 4.7 mol) in water (160 ml) added dropwise.
The resulting black suspension was extracted with ether (2*500 ml), the extracts combined, dried (MgSO4), and evaporated to give 2-bromo-5-picoline as a tan solid (24 g, 75percent); δH (CDCl3) 2.30 (3H, s, CH3), 7.38 (2H, s, 3-H, 4-H)
8.21 (1H, s, 6-H).
This was converted in two steps, using the procedure outlined in Example 10, to the title compound, m.p. 204°-205° C. (EtOAc); (Found: C, 70.53; H, 6.86; N, 22.86. C18 H21 N5 requires C, 70.33; H, 6.89; N, 22.78percent); δH (DMSO-d6) 2.12 (3H, s, ArCH3), 2.47 (4H, m, 2*piperazinyl CH2), 3.39 (4H, m, 2*piperazinyl CH2), 3.66 (2H, s, CH2 N), 6.70 (1H, d, J 8.6 Hz, 3'-H), 7.04 (1H, dd, J 7.8, 4.7 Hz, 5-H), 7.34 (1H, dd, J 8.6, 2.3 Hz, 4'-H), 7.36 (1H, d, J 2.3 Hz, 2-H), 7.92 (1H, d, J 2.3
Hz, 6'-H), 8.05 (1H, dd, J 7.8, 1.2 Hz, 4-H), 8.19 (1H, dd, J 4.7, 1.5 Hz, 6-H), and 11.45 (1H, br s, NH); m/z (CI+, NH3) 308 (M+1)+.
Reference: [1] Patent: US5432177, 1995, A,
  • 4
  • [ 108-99-6 ]
  • [ 3510-66-5 ]
Reference: [1] Chemical Communications, 2000, # 11, p. 951 - 952
[2] European Journal of Organic Chemistry, 2012, # 9, p. 1746 - 1752
  • 5
  • [ 1603-41-4 ]
  • [ 3510-66-5 ]
Reference: [1] Patent: US4574125, 1986, A,
  • 6
  • [ 1003-68-5 ]
  • [ 3510-66-5 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
  • 7
  • [ 624-28-2 ]
  • [ 74-88-4 ]
  • [ 3510-66-5 ]
Reference: [1] Green Chemistry, 2011, vol. 13, # 5, p. 1110 - 1113
[2] Australian Journal of Chemistry, 2013, vol. 66, # 2, p. 199 - 207
  • 8
  • [ 6457-37-0 ]
  • [ 3510-66-5 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 9, p. 1746 - 1752
  • 9
  • [ 115185-81-4 ]
  • [ 3510-66-5 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
  • 10
  • [ 3060-42-2 ]
  • [ 3510-66-5 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
  • 11
  • [ 18368-64-4 ]
  • [ 3510-66-5 ]
Reference: [1] Patent: EP3184527, 2017, A1, . Location in patent: Paragraph 0624
  • 12
  • [ 3510-66-5 ]
  • [ 68-12-2 ]
  • [ 4985-92-6 ]
YieldReaction ConditionsOperation in experiment
39% With n-butyllithium In diethyl ether at -78℃; for 2 h; For the synthesis of 5-methylpyridin-2-carbaldehyde (B; n = 1 ; R1 , R2, R4 = H; R3 = Me) 50 g (290 mmol) 2-bromo-5-methylpyridinβ (B2; R1, R2, R4 = H; R3 = Me) was dissolved in 2500 ml diethylether and cooled to -78°C. Then, 150 ml (380 mmoi) nBuLi was added drop wise and the reaction mixture was stirred for 2hrs at -78° C. DMF (31.5 ml, 407 mmol) was added drop wise and after the reaction mixture was allowed to warm to room temperature, water was added to the reaction mixture. Both, organic and aqueous layer were separated and the water layer was extracted with ethyl acetate for three times. All organic layers were combined, washed with brine, dried over Na2SO4 and the solvent was evaporated in vacuo yielding a brown oil. This residue was purified by flash chromatography with heptane (supplemented with ethyl acetate from 0 to 25percent). Yield: 19 g (39percent) brown solid.MS (APCI): m/z 122 (M+1)+. 1H NMR (CDCI3, 360 MHz) δ (ppm): 2.48 (s, 3H, CH3); 7.70 (dd, J=7.9 Hz1 2.0 Hz, 1H, pyridine H4); 7.91 (d, J=7.7 Hz1 1H, pyridine H3); 8.68 (s, 1H, pyridine H6); 10.10 (s, 1H, aldehyde).
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 8, p. 2238 - 2243[2] Angew. Chem., 2018, vol. 130, # 8, p. 2260 - 2265,6
[3] Patent: WO2009/60030, 2009, A1, . Location in patent: Page/Page column 38-39
[4] Chemistry - A European Journal, 2008, vol. 14, # 17, p. 5313 - 5328
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6763 - 6770
  • 13
  • [ 3510-66-5 ]
  • [ 4434-13-3 ]
Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 1932,1934
  • 14
  • [ 3510-66-5 ]
  • [ 19230-58-1 ]
YieldReaction ConditionsOperation in experiment
75% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; [0146] To a solution of 2-bromo-5-methylpyridine (4 g, 2.3 mmol) in dichloromethane (500 mL) was added m-CPBA (52 g, 304 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 20 hours and the then the pH was adjusted to about 9 with a saturated solution of K2CO3. The organic layers were separated and concentrated to give a residue which was purified by flash silica chromatography eluted with petroleum ether/ethyl acetate (1 : 1) to give 2-bromo-5-methylpyridine 1-oxide (33g; 75percent). 1H NMR (CDCL3): δ ppm 8.25 (s, 1H), 8.75 (d, 1H, J= 8.4Hz), 6.95-6.94 (m, 1H), 2.30 (s, 3H).
71% With 3-chloro-benzenecarboperoxoic acid In chloroform at 50℃; for 3 h; To a mixture of 2-bromo-5-methylpyridine (4.0 g, 23.3 mmol) in CHCl3(20 mL) was added m-CPBA (5.2 g, 29.8 mmol) and the reaction was stirred at 50° C. for 3 hrs. The mixture was cooled and filtered. The filtrate was washed with 5percent aqueous NaOH solution and the organic layer was separated, dried over anhydrous Na2SO4and concentrated to dryness. The residue was purified by column chromatography on silica gel (eluted with DCM: MeOH=100:0 to 100:1) to give the title compound (3.1 g, 71percent yield) as a colorless oil. LC/MS (ESI) m/z: 188 (M+H)
Reference: [1] Patent: WO2011/146287, 2011, A1, . Location in patent: Page/Page column 29-30
[2] Patent: WO2017/35353, 2017, A1, . Location in patent: Paragraph 0911
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 16, p. 7126 - 7135
[4] Journal of Organic Chemistry, 2009, vol. 74, # 2, p. 939 - 942
  • 15
  • [ 3510-66-5 ]
  • [ 38203-08-6 ]
YieldReaction ConditionsOperation in experiment
80% With n-butyllithium In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; acetonitrile Step 3-Preparation of 2-(5-methylpyridin-2-yl)acetonitrile
To a solution of anhydrous acetonitrile (10.1 mL, 191.83 mmol, 3.3 equiv.) in dry THF (500 mL) was added dropwise n-butyl lithium (2.5 M in hexane, 69.8 mL, 174.39 mmol, 3 equiv.) at minus 78° C. under nitrogen atmosphere.
The resulting white suspension was stirred at minus 78° C. for 1 hour, and then a solution of 2-bromo-5-methylpyridine (10.0 g, 58.13 mmol, 1 equiv.) in dry THF (30 mL) was added.
The reaction mixture was kept at minus 78° C. for 1 hour and then warmed up slowly to room temperature and stirred for another hour.
Ice water was added and the layer was separated.
The organic layer was washed with water and brine, dried over MgSO4, filtered, and evaporated to give 18 g of crude product.
The crude product was purified by silica-gel column chromatography (eluent, PE/EtOAc=15:1) to give 2-(5-methylpyridin-2-yl)acetonitrile (6.2 g, yield 80percent).
1H NMR (300 MHz, CDCl3): δ 8.40 (d, J=3.0 Hz, 1H), 7.54 (dd, J1=3.0 Hz, J2=6.0 Hz, 1H), 7.32 (d, J=6.0 Hz, 1H), 3.90 (s, 2H), 2.40 (s, 3H).
Reference: [1] Patent: US2009/280230, 2009, A1,
[2] Patent: US2009/280230, 2009, A1,
[3] Patent: US2009/280230, 2009, A1,
  • 16
  • [ 3510-66-5 ]
  • [ 75-05-8 ]
  • [ 38203-08-6 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 2 h;
To a solution of anhydrous acetonitrile (10.1 mL, 191.83 mmol, 3.3 equiv.) in dry THF (500 mL) was added dropwise n-butyl lithium (2.5 M in hexane, 69.8 mL, 174.39 mmol, 3 equiv.) at minus 78° C. under nitrogen atmosphere. The resulting white suspension was stirred at minus 78° C. for 1 hour, and then a solution of 2-bromo-5-methylpyridine (10.0 g, 58.13 mmol, 1 equiv.) in dry THF (30 mL) was added. The reaction mixture was kept at minus 78° C. for 1 hour and then warmed up slowly to room temperature and stirred for another hour. Ice water was added and the layer was separated. The organic layer was washed with water and brine, dried over MgSO4, filtered, and evaporated to give 18 g of crude product. The crude product was purified by silica-gel column chromatography (eluent, PE/EtOAc=15:1) to give 2-(5-methylpyridin-2-yl)acetonitrile (6.2 g, yield 80percent). 1H NMR (300 MHz, CDCl3): δ 8.40 (d, J=3.0 Hz, 1H), 7.54 (dd, J1=3.0 Hz, J2=6.0 Hz, 1H), 7.32 (d, J=6.0 Hz, 1H), 3.90 (s, 2H), 2.40 (s, 3H).
Reference: [1] Patent: US8148536, 2012, B2, . Location in patent: Page/Page column 79
[2] Patent: US8148536, 2012, B2, . Location in patent: Page/Page column 73
  • 17
  • [ 3510-66-5 ]
  • [ 6311-35-9 ]
YieldReaction ConditionsOperation in experiment
44% With potassium permanganate; Aliquat 336 In water at 110℃; for 2.5 h; After dissolving 2-bromo-5-picoline (100 g, 0.291 mol) in 1000 ml of water, Aliquat336 (2 ml) was added, and then potassium permanganate (251 g, 0.797 mol) was gradually added over a period of 1 hour and 30 minutes while stirring at 110°C. This mixture was further stirred for an hour, the reaction mixture was filtered through celite without cooling and washed with water, and the filtrate was concentrated to approximately half volume under reduced pressure. After adding 48percent hydrobromic acid (.similar.300 ml), the precipitated crystals were filtered, washed with water and dried to yield the title compound (white crystals 52 g, 44percent).1H-NMR(CDCl3)δ(ppm) 7.64(1H,d,J=8.0Hz), 8.08(1H,d,J=8.0Hz), 9.03(1H,s).
Reference: [1] Synthesis, 1994, # 1, p. 87 - 92
[2] Journal of Materials Chemistry, 2005, vol. 15, # 48, p. 5164 - 5173
[3] Patent: EP1391451, 2004, A1, . Location in patent: Page 143
[4] Journal of Organic Chemistry, 1949, vol. 14, p. 509,513
[5] Synthesis, 2003, # 4, p. 551 - 554
[6] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 21, p. 4681 - 4684
  • 18
  • [ 3510-66-5 ]
  • [ 6271-78-9 ]
Reference: [1] Journal of Organic Chemistry, 1949, vol. 14, p. 509,513
  • 19
  • [ 3510-66-5 ]
  • [ 64-17-5 ]
  • [ 201230-82-2 ]
  • [ 55876-82-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 18, p. 4494 - 4506
  • 20
  • [ 3510-66-5 ]
  • [ 26218-78-0 ]
Reference: [1] Journal of Organic Chemistry, 1949, vol. 14, p. 509,513
  • 21
  • [ 3510-66-5 ]
  • [ 1802-30-8 ]
Reference: [1] Chemistry - A European Journal, 1998, vol. 4, # 11, p. 2237 - 2250
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
  • 22
  • [ 3510-66-5 ]
  • [ 13598-45-3 ]
  • [ 110-18-9 ]
  • [ 7446-09-5 ]
  • [ 65938-77-4 ]
Reference: [1] Patent: US6017945, 2000, A,
  • 23
  • [ 3510-66-5 ]
  • [ 4931-01-5 ]
YieldReaction ConditionsOperation in experiment
69% for 24 h; Heating / reflux A mixture OF 2-BROMO-5-METHYLPYRIDINE (25G, 0. 15MOL) and hydrazine monohydrate (100MOL) was stirred at reflux for 24 hours, the reaction mixture was allowed to cool to room temperature and then added to water (100MOL). The product was precipitated by the addition of sodium chloride and the resultant solid was filtered off and dried in a vacuum desiccator to give 23.9g (69percent pure) of white crystals.
Reference: [1] Patent: WO2004/41940, 2004, A1, . Location in patent: Page 8
  • 24
  • [ 3510-66-5 ]
  • [ 201230-82-2 ]
  • [ 29681-38-7 ]
Reference: [1] Patent: EP1466902, 2004, A1, . Location in patent: Page 34
  • 25
  • [ 3510-66-5 ]
  • [ 29681-38-7 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 9, p. 2930 - 2934
  • 26
  • [ 3510-66-5 ]
  • [ 124-41-4 ]
  • [ 13472-56-5 ]
YieldReaction ConditionsOperation in experiment
91% at 90℃; for 17 h; EXAMPLE 5
Preparation of 2-methoxy-5-methylpyridine From 2-bromo-5-methylpyridine
250 g of 2-bromo-5-methylpyridine (1.45 mol) are introduced into a mixture of 2.1 g of copper(I) bromide (CuBr, 1 mol percent), 14.5 g (2 mol percent) of polyethylene glycol dimethyl ether 500 and 457 g of sodium methanolate solution in methanol (30percent strength) (precursor concentration 14.5percent) and heated to 90° C.
After the conversion, determined by GC, it is >98.5percent (total of 17 h), the reaction mixture is added to 750 g of water.
The mixture is brought to pH 9 by metering in hydrochloric acid and is then filtered through decalite.
The mixture is extracted twice with 350 g of MTBE each time.
Vacuum fractionation of the combined organic phases results in 162.8 g of 2-methoxy-5-methylpyridine (1.32 mol, 91percent), GC purity >98percent a/a.
Reference: [1] Patent: US2008/71084, 2008, A1, . Location in patent: Page/Page column 4
  • 27
  • [ 3510-66-5 ]
  • [ 23100-12-1 ]
Reference: [1] Synthesis, 1994, # 1, p. 87 - 92
  • 28
  • [ 3510-66-5 ]
  • [ 127-19-5 ]
  • [ 5308-63-4 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 0.166667 h;
Stage #2: at -78℃; for 2 h;
[Referential Example 35] 5-(5-Methyl-2-pyridyl)-1-(2-pyridyl)-1H-pyrazole-3-carboxylic acid; [Show Image] 1) 1-(5-Methyl-2-pyridyl)ethanone; n-Butyllithium (1.58M solution in hexane, 24 ml) was added to a solution of 2-bromo-5-picoline (5.0 g) in diethylether (100 ml) in 5 minutes at -78°C, and the mixture was stirred for 5 minutes. N,N-Dimethyl acetamide (3.5 ml) was added to the reaction liquid at the same temperature, and the mixture was stirred for 2 hours. Water and ethyl acetate were added to the reaction liquid and the phases were separated, and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane-ethyl acetate) to give 1-(5-methyl-2-pyridyl)ethanone (3.43 g, 87percent) as an oily product. 1H-NMR (400 MHz, CDCl3)δ: 2.42 (3H, s), 2.71 (3H, s), 7.62 (1H, dd, J = 1.59, 7.93 Hz), 7.94 (1H, d, J = 7.93 Hz), 8.50 (1H, s).
87%
Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 0.166667 h;
Stage #2: for 2 h;
1)
1-(5-Methyl-2-pyridyl)ethanone
At -78°C, n-butyllithium (1.58M hexane solution, 24 mL) was added dropwise to 2-bromo-5-picoline (5.0 g) in diethyl ether (100 mL) over 5 minutes, followed by stirring for 5 minutes.
Subsequently, N,N-dimethylacetamide (3.5 mL) was added dropwise to the reaction mixture, followed by stirring for 2 hours.
The reaction mixture was partitioned between water and ethyl acetate.
The organic layer was dried over magnesium sulfate anhydrate.
After a filtration step, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane - ethyl acetate), to thereby give 1-(5-methyl-2-pyridyl)ethanone as an oily product (3.43 g, 87percent).
1H-NMR(400MHz,CDCl3)δ:2.42(3H,s), 2.71(3H,s), 7.62(1H,dd,J=1.59,7.93Hz), 7.94(1H,d,J=7.93Hz), 8.54(1H,s).
87%
Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 0.166667 h;
Stage #2: for 2 h;
2) 1-(5-Methyl-2-pyridyl)-1-ethanone n-Butyllithium (a 1.58 M solution in hexane, 24 mL) was added dropwise to a solution of 2-bromo-5-picoline (5.0 g) in diethyl ether (100 mL) over 5 minutes under cooling to -78°C, and then the resultant mixture was stirred for 5 minutes. N, N-dimethylacetamide (3.5 mL) was added dropwise to the reaction solution, and then the mixture was stirred for 2 hours. Water and ethyl acetate were added to the reaction solution, and the mixture was partitioned. The organic layer was dried over anhydrous magnesium sulfate. After separation by filtration, a residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane-ethyl acetate), to obtain 1-(5-methyl-2-pyridyl)-1-ethanone (3.43 g, 87percent) as an oily product. 1H-NMR(400MHz, CDCl3)δ: 2.42(3H, s), 2.71(3H, s), 7.62(1H, dd, J=1.59, 7.93Hz), 7.94(1H, d, J=7.93Hz), 8.54(1H, s).
72%
Stage #1: With n-butyllithium In hexanes; diethyl ether at -78 - -40℃; for 0.25 h;
Stage #2: at -78℃; for 2 h;
Stage #3: With ammonium chloride In hexanes; diethyl ether; water
To a solution of 2-bromo-5-methyl pyridine 23 (1.73 g, 10 mmol) in dry ether (20 ml), cooled to -78 0C, was added n-butyllithium (6.25 ml of 1.6M solution in hexanes, 10 mmol, 1 equiv) dropwise. The reaction mixture was allowed to warm to -40 0C for 15 min, then cooled back to -78 0C again. N,N-dimethylacetamide (1.023 ml, 1 1 mmol, 1.1 equiv) was added dropwise and the mixture was stirred at -78 0C for 2h. Saturated aqueous ammonium chloride (10 ml) was added and the organic layer was separated. The aqueous <n="24"/>layer was extracted with ether (3 x 10 ml) and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give an oily residue that was subjected to flash column chromatography using (5percent methanol in methylene chloride) to give compound 25 (0.977 g, 72percent) as a yellow oil: TLC R/= 0.48 (silica gel, 25percent EtOAc/hexanes); 1H NMR (400 MHz, CDCl3) δ 8.5-8.48 (broad s, IH), 7.94 (d, J= 8.0 Hz, IH), 7.63-7.60 (m, IH), 2.70 (s, 3H), 2.41 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 200.2, 151.7, 149.7, 137.8, 137.4, 121.7, 26.0, 18.9; HRMS calcd for C8H9NO + Na+ 158.0582; found 158.0580 [M + Na+].

Reference: [1] Inorganic Chemistry, 2018,
[2] Patent: EP1698626, 2006, A1, . Location in patent: Page/Page column 48
[3] Patent: EP1762568, 2007, A1, . Location in patent: Page/Page column 30
[4] Patent: EP1785418, 2007, A1, . Location in patent: Page/Page column 38
[5] Chemistry - A European Journal, 2008, vol. 14, # 2, p. 570 - 581
[6] Angewandte Chemie - International Edition, 2016, vol. 55, # 16, p. 4962 - 4966[7] Angew. Chem., 2016, vol. 128, p. 5046 - 5050,5
[8] Patent: WO2008/118327, 2008, A1, . Location in patent: Page/Page column 22-23; Sheet3/13
[9] Angewandte Chemie - International Edition, 2017, vol. 56, # 40, p. 12102 - 12106[10] Angew. Chem., 2017, vol. 129, # 40, p. 12270 - 12274,5
[11] New Journal of Chemistry, 2008, vol. 32, # 6, p. 1048 - 1054
  • 29
  • [ 3510-66-5 ]
  • [ 21543-49-7 ]
Reference: [1] Synthesis, 1994, # 1, p. 87 - 92
  • 30
  • [ 3510-66-5 ]
  • [ 77152-08-0 ]
  • [ 1620-71-9 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 22, p. 11126 - 11146
  • 31
  • [ 3510-66-5 ]
  • [ 101990-45-8 ]
YieldReaction ConditionsOperation in experiment
89% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 85℃; for 0.5 h; (Referential Example 8)
Synthesis of 2-bromo-5-(bromomethyl)pyridine (referential compound 8)
N-Bromosuccinimide (16 g, 91 mmol) and 0.40 g (2.4 mmol) of 2,2'-azobis(isobutyronitrile) were added to a solution of 12 g (70 mmol) of 2-bromo-5-methylpyridine in 100 ml of 1,2-dichloroethane and the mixture was stirred at 85°C. After 15 minutes, 0.40 g (2.4 mmol) of 2,2'-azobis(isobutyronitrile) was added thereto and the mixture was stirred for 15 minutes.
After the reaction was finished, water was added to the reaction solution and the organic layer was separated therefrom.
The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo.
The resulting residue was subjected to a silica gel column chromatography (eluding solvent: n-hexane: ethyl acetate = 10:1 to 9:1 (v/v)) and the fraction containing the aimed substance was concentrated in vacuo to give 15 g of the title compound as white powder (yield: 89percent).
Rf value: 0.63 (n-hexane: ethyl acetate = 9:1 (v/v))
Mass spectrum (CI, m/z): 250, 252, 254 (M+ + 1)
1H-NMR spectrum (CDCl3, δ ppm): 4.42 (s, 2H), 7.49 (d, J = 8.3Hz, 1H), 7.61 (dd, J1 = 8.3Hz, J2 = 2.7Hz, 1H), 8.39 (d, J = 2.7Hz, 1H)
59% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethaneReflux Synthesized from 2-bromo-5-methylpyridine (3.00 g, 17.40 mmol), NBS (3.41 g, 19.20 mmol) and DBPO (230 mg, 0.80 mmol) in carbon tetrachloride according to Method A. Yield: 2.56 g (59 percent); lachrymatory yellow needles; 1 H NMR (CDCIs, 500 MHz): δΗ (ppm) = 4.14 (s, 2H), 7.47 (d, J = 8.2 Hz, 1 H), 7.59 (d, J = 8.2 Hz, 1 H), 8.38 (s, 1 H); MS (ESI): m/z = 252.37 [M+H]+.Methylpyridine was dissolved in 40 ml_ of dry carbon tetrachloride. To this solution was added /V-bromsuccinimide (NBS) (1.1 eq) and benzoyl peroxide (5 molpercent) and the mixture was refluxed over night. After cooling, the succinimide was removed by filtration and the filtrate was concentrated under vacuum. The crude product was further purified by flash column chromatography on silica gel using a mixture of petroleum ether / ethyl acetate (95:5) as eluent.
52.6% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 80℃; for 2 h; Inert atmosphere To a solution of 169-51 (5.0 g, 29.1 mmol) in Cd4 (40 mL) was added NBS (5.22 g, 29.1 mmol) and BPO (350 mg, 1.4 mmol). The reaction mixture was stirred at 80 °C under an atmosphere of nitrogen for 2 hours. The mixturewas diluted with DCM, washed with water and brine, dried, and concentrated to dryness. The remaining residue was purified by column chromatography on silica gel (eluted with PE/EtOAc = 120:1) to afford 169-S2 (3.81g, 52.6percent yield) as a yellow oil. LC/MS (ESI) m/z: 250 (M+H)t
49% With N-Bromosuccinimide In tetrachloromethane for 4 h; Heating / reflux 2-Bromo-5-bromomethylpyridine. 2-Bromo-5-methylpyridine (5.00 g, 29.1 mmoles) and N-bromosuccinimide (5.22 g, 29.3 mmoles) were dissolved in carbon tetrachloride (40 mL) under nitrogen. Benzoyl peroxide (0.35 g, 1.4 mmoles) was added and the mixture heated at reflux for four hours. The mixture was cooled to room temperature, filtered, and washed with NaHCO3/H2O. The mixture was adsorbed onto silica gel and then chromatographed. eluting with a gradient of hexane to 10percent ethyl acetate/hexane. Pure fractions were combined and concentrated to provide the desired mono-brominated product as a pale yellow solid, 3.60 g (49percent). LC/MS (M+H)+ m/z=249.8, 251.8, 253.8.
49%
Stage #1: With N-Bromosuccinimide In tetrachloromethane for 4 h; Inert atmosphere; Reflux
Stage #2: With sodium hydrogencarbonate In tetrachloromethane; water at 20℃;
Step A2-Bromo-5-bromomethylpyridine. 2-Bromo-5-methylpyridine (5.00 g, 29.1 mmoles) and N-bromosuccinimide (5.22 g, 29.3 mmoles) were dissolved in carbon tetrachloride (40 mL) under nitrogen. Benzoyl peroxide (0.35 g, 1 .4 mmoles) was added and the mixture heated at reflux for four hours. The mixture was cooled to room temperature, filtered, and washed with NaHC03/H2O.The mixture was adsorbed onto silica gel and thenchromatographed. eluting with a gradient of hexane to 10percent ethyl acetate/hexane. Pure fractions were combined and concentrated to provide the desired mono-brominated product as a pale yellow solid, 3.60 g (49percent). LC/MS (M+H)+ m/z = 249.8, 251.8, 253.8.
46% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane at 55℃; for 6 h; Heating; Irradiation Example 16 Step 1: A mixture of 2-bromo-5-methylpyridine (10 g, 58 MMOL), N-bromosuccinimide (15.5 g, 87.2 MMOL), and AZOBISISOBUTYRONITRILE (0.25 g) in anhydrous CH2CI2 (100 ml) was heated at 55 °C under irradiation (200W lamp) for 6 h. The mixture was cooled down to RT, diluted with CH2CI2 (200 ML), washed with saturated NaHCO3 solution, dried (MGS04), filtered and concentrated. The residue was subjected to silica gel flash chromatography (5<7percent EtOAc/hexanes) to afford the product (6.75 g, 46percent).
20% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 19 h; Reflux Synthesis Example 18
N-[1-((6-bromopyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound 231)
An amount of 500 mg (2.92 mmol) of 2-bromo-5-methylpyridine was dissolved in 15 mL of carbon tetrachloride, following which 623 mg (3.50 mmol) of N-bromosuccinimide and 10 mg of benzoyl peroxide were added and the mixture was refluxed under heating for 19 hours.
Following reaction completion, the reaction mixture was returned to room temperature and concentrated under reduced pressure, then purified by silica gel column chromatography (hexane/ethyl acetate=19:1), giving 143 mg of 2-bromo-5-bromomethylpyridine (yield, 20percent).
1H-NMR (CDCl3, δ, ppm): 4.42 (2H, s), 7.47 (1H, d), 7.59 (1H, dd), 8.38 (1H, d)
20% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 19 h; Reflux 500 mg (2.92 mmol) of 2-bromo-5-methylpyridine was dissolved in 15 ml of carbon tetrachloride, 623 mg (3.50 mmol) of N-bromosuccinimide and 10 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed for 19 hours. After the reaction was completed, the reaction solution was returned to room temperature, concentrated under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate = 19:1) to obtain 143 mg (yield 20percent) of 2-bromo-5-bromomethylpyridine. [0250] 1H-NMR (CDCl3, δ, ppm): 4.42(2H, s), 7.47(1H, d), 7.59(1H, dd), 8.38(1H, d)
20% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 19 h; Reflux 500 mg (2.92 mmol) of 2-bromo-5-methylpyridine was dissolved in 15 ml of carbon tetrachloride, 623 mg (3.50 mmol) of N-bromosuccinimide and 10 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed for 19 hours. After the reaction was completed, the reaction solution was returned to room temperature, concentrated under reduced pressure and purified by silica gel column chromatography (hexane: ethyl acetate = 19:1) to obtain 143 mg (yield 20percent) of 2-bromo-5-bromomethylpyridine. [0240] 1H-NMR (CDCl3, δ, ppm) : 4.42(2H, s), 7.47 (1H, d), 7.59 (1H, dd), 8.38 (1H, d)
20% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 19 h; Reflux In 15 ml of carbon tetrachloride, 500 mg (2.92 mmol) of 2-bromo-5-methylpyridine was dissolved.
To this solution, 623 mg (3.50 mmol) of N-bromosuccinimide and 10 mg of benzoyl peroxide were added, followed by heating under reflux for 19 hours.
After completion of the reaction, the reaction liquid was returned to room temperature, and concentrated under reduced pressure.
The residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1).
Thus, 143 mg of 2-bromo-5-bromomethylpyridine was obtained (Percentage Yield: 20percent).
1H-NMR (CDCl3, δ, ppm): 4.42 (2H, s), 7.47 (1H, d), 7.59 (1H, dd), 8.38 (1H, d)

Reference: [1] Patent: EP1679308, 2006, A1, . Location in patent: Page/Page column 35
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1992 - 2010
[3] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 1, p. 2 - 6
[4] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 8, p. 559 - 564
[5] Patent: WO2012/52540, 2012, A1, . Location in patent: Page/Page column 47; 48-49
[6] Patent: WO2018/160889, 2018, A1, . Location in patent: Page/Page column 602; 603
[7] Patent: US2005/192302, 2005, A1, . Location in patent: Page/Page column 23
[8] Patent: WO2012/114223, 2012, A1, . Location in patent: Page/Page column 40
[9] Patent: WO2005/16876, 2005, A2, . Location in patent: Page/Page column 69
[10] Journal of Medicinal Chemistry, 2013, vol. 56, # 15, p. 6022 - 6032
[11] Patent: US2013/150414, 2013, A1, . Location in patent: Paragraph 0406; 407
[12] Patent: EP2633756, 2013, A1, . Location in patent: Paragraph 0249; 0250
[13] Patent: EP2634174, 2013, A2, . Location in patent: Paragraph 0239; 0240
[14] Patent: EP2749555, 2014, A1, . Location in patent: Paragraph 0122
[15] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 15, p. 1989 - 1992
[16] Patent: US2003/8861, 2003, A1,
[17] Patent: US2002/22633, 2002, A1,
[18] Patent: US5861420, 1999, A,
[19] Patent: US6127390, 2000, A,
[20] Patent: WO2008/8747, 2008, A1, . Location in patent: Page/Page column 35, 63
[21] Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 1, p. 204 - 212
[22] Patent: WO2009/74829, 2009, A1, . Location in patent: Page/Page column 52-53
[23] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 17, p. 5071 - 5074
[24] Patent: US2011/9409, 2011, A1, . Location in patent: Page/Page column 36-37
[25] Patent: US2011/178101, 2011, A1, . Location in patent: Page/Page column 34
[26] Patent: WO2013/43232, 2013, A2, . Location in patent: Paragraph 00626
[27] Journal of Medicinal Chemistry, 2013, vol. 56, # 15, p. 6234 - 6247
[28] Patent: US2015/368248, 2015, A1, . Location in patent: Paragraph 0089
[29] Patent: WO2017/156165, 2017, A1, . Location in patent: Paragraph 00615-00617
  • 32
  • [ 3510-66-5 ]
  • [ 101990-45-8 ]
  • [ 154321-32-1 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 9, p. 1697 - 1700
[2] Tetrahedron Letters, 2002, vol. 43, # 9, p. 1697 - 1700
[3] Synthesis, 1994, # 1, p. 87 - 92
[4] Patent: US2007/219276, 2007, A1, . Location in patent: Page/Page column 41
  • 33
  • [ 3510-66-5 ]
  • [ 101990-45-8 ]
Reference: [1] Patent: US5196537, 1993, A,
[2] Patent: US5451593, 1995, A,
  • 34
  • [ 3510-66-5 ]
  • [ 101990-45-8 ]
Reference: [1] Patent: US6090828, 2000, A,
  • 35
  • [ 3510-66-5 ]
  • [ 101990-45-8 ]
  • [ 154321-32-1 ]
Reference: [1] Organic Letters, 2000, vol. 2, # 24, p. 3845 - 3848
  • 36
  • [ 3510-66-5 ]
  • [ 128-08-5 ]
  • [ 101990-45-8 ]
Reference: [1] Patent: WO2003/106455, 2003, A1, . Location in patent: Page 55
  • 37
  • [ 3510-66-5 ]
  • [ 149806-06-4 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 36, p. 6033 - 6036
[2] Synthesis, 1994, # 1, p. 87 - 92
[3] Synthesis, 1994, # 1, p. 87 - 92
[4] Patent: WO2016/124747, 2016, A1,
[5] Patent: US2018/202388, 2018, A1,
  • 38
  • [ 3510-66-5 ]
  • [ 308846-06-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 17, p. 3612 - 3622
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 7, p. 1017 - 1022
[3] Patent: WO2011/20615, 2011, A1,
[4] Patent: EP2289883, 2011, A1,
[5] Patent: WO2012/128582, 2012, A2,
  • 39
  • [ 3510-66-5 ]
  • [ 120740-10-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 15, p. 6234 - 6247
  • 40
  • [ 3510-66-5 ]
  • [ 848093-05-0 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 2, p. 156 - 161
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 3510-66-5 ]

Bromides

Chemical Structure| 109-04-6

[ 109-04-6 ]

2-Bromopyridine

Similarity: 0.89

Chemical Structure| 120740-10-5

[ 120740-10-5 ]

(6-Bromopyridin-3-yl)methanamine

Similarity: 0.86

Chemical Structure| 139585-70-9

[ 139585-70-9 ]

6-Bromonicotinonitrile

Similarity: 0.84

Chemical Structure| 122306-01-8

[ 122306-01-8 ]

(6-Bromopyridin-3-yl)methanol

Similarity: 0.84

Chemical Structure| 149806-06-4

[ 149806-06-4 ]

6-Bromonicotinaldehyde

Similarity: 0.83

Related Parent Nucleus of
[ 3510-66-5 ]

Pyridines

Chemical Structure| 109-04-6

[ 109-04-6 ]

2-Bromopyridine

Similarity: 0.89

Chemical Structure| 120740-10-5

[ 120740-10-5 ]

(6-Bromopyridin-3-yl)methanamine

Similarity: 0.86

Chemical Structure| 139585-70-9

[ 139585-70-9 ]

6-Bromonicotinonitrile

Similarity: 0.84

Chemical Structure| 122306-01-8

[ 122306-01-8 ]

(6-Bromopyridin-3-yl)methanol

Similarity: 0.84

Chemical Structure| 149806-06-4

[ 149806-06-4 ]

6-Bromonicotinaldehyde

Similarity: 0.83