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Product Details of [ 5632-15-5 ]

CAS No. :5632-15-5 MDL No. :MFCD08062399
Formula : C10H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :NNAYPIDFVQLEDK-UHFFFAOYSA-N
M.W : 222.08 Pubchem ID :12417418
Synonyms :

Calculated chemistry of [ 5632-15-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.58
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.23
Log Po/w (XLOGP3) : 2.78
Log Po/w (WLOGP) : 2.98
Log Po/w (MLOGP) : 2.58
Log Po/w (SILICOS-IT) : 3.47
Consensus Log Po/w : 2.81

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.52
Solubility : 0.0672 mg/ml ; 0.000303 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.436 mg/ml ; 0.00196 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.96
Solubility : 0.00241 mg/ml ; 0.0000109 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 5632-15-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P264-P270-P280-P301+P312+P330-P305+P351+P338+P310-P501 UN#:1759
Hazard Statements:H302-H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5632-15-5 ]

* 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 [ 5632-15-5 ]
  • Downstream synthetic route of [ 5632-15-5 ]

[ 5632-15-5 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 91-63-4 ]
  • [ 5632-15-5 ]
YieldReaction ConditionsOperation in experiment
76% With tert.-butylhydroperoxide; copper(I) bromide In water; acetonitrile at 70℃; for 8 h; General procedure: 2-Methylquinoline derivatives (0.5mmol), cuprous halide (0.75mmol), TBHP (8.0 eq., 70percent aqueous solution) and CH3CN (2mL) were stirred at 70 °C for 8h. Then, the reaction mixture was diluted by water and extracted with CH2Cl2 (3×15mL). The X2 (X=I, Br, Cl) in organic phase was quenched by Na2S2O3. The combined organic layers were washed with saturated NH4Cl aqueous solution and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. The desired product was obtained by silica gel chromatography (petroleum ether/ethyl acetate, v/v=10/1).
55% With tetra-(n-butyl)ammonium iodide; ethylene dibromide; urea In acetonitrile at 95℃; for 0.5 h; Microwave irradiation General procedure: 2-Methylquinolines 1(2 mmol), TBAI (2 mmol), urea (2 mmol), 1,2-dibromoethane (6 mL), andacetonitrile (6 mL) were mixed in a microwave tube. The reaction mixture was stirred at 95 °C for 30 min under microwave irradiation using a CEM Discover microwave reactor (the highest power: 150 W; run time: 5 min; holdtime: 30 min; temperature: 95 °C). The resulting reaction mixture was concentrated in vacuo, and the crude residue was purified by flash chromatography on silica gel using hexane/EtOAc as eluent.
52% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 5 h; Reflux; Inert atmosphere; Schlenk technique General procedure: The respective 2-methylquinoline (14–20mmol) was dissolved in carbon tetrachloride or benzene (1.3–13.5ml per mmol) and N-bromosuccinimide (1.1 eqv) was added. The mixture was refluxed in the presence of benzoyl peroxide (0.8–1.7mmol) for the indicated below amount of time. After cooling to room temperature, the precipitated succinimide was filtered off and after evaporation af the volatiles under vacuum, the product was purified by flash chromatography.
23.2% With N-Bromosuccinimide In tetrachloromethane for 12 h; Selective bromination of the2-methyl quinoline (3.0 g, 32.2 mmol) with 1.5 equivalents of NBSin CCl4 for 12 h afforded 1.3 g of compound 1 in 23.2percent yield asyellow solid. The solid was characterized by 1H NMR (Figure S-1)(300 MHz, in ppm CDCl3): d 8.187–8.159 (d, J = 8.4 Hz, 1H), 8.104–8.076 (d, J = 8.4 Hz, 1H), 7.832–7.804 (d, J = 8.4 Hz, 1H), 7.770–7.714(m,1H), 7.589–7.538 (t, J = 8.4 Hz, 2H), 4.730 (s, 2H). 13C NMR(Figure S-2) (75 MHz, CDCl3): d 156.86, 147.50, 137.25, 129.92,129.25, 127.50, 127.43, 127.31, 127.00, 121.13, 34.37.
10% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethaneHeating / reflux 2-(bromomethyl)quinoline.
To a solution of quinaldine (500 mg, 3.49 mmol) in CCl4 (50 ml) was added NBS (621 mg, 3.49 mmol) and AIBN (28 mg, 0.174 mmol).
This mixture was refluxed overnight.
The reaction was cooled to 0° C. and filtered to remove any undissolved solids.
The filtrate was concentrated under vacuum.
Column chromatography on silica gel (0-12percent ethyl acetate/hexanes) afforded intermediate 3 (71 mg, 0.319 mmol, 10percent).
1H NMR (400 MHz, CDCl3) δ ppm 8.18 (d, J=8.31 Hz, 1H), 8.07 (d, J=8.56 Hz, 1H), 7.81 (d, J=8.06 Hz, 1H), 7.69-7.77 (m, 1H), 7.51-7.60 (m, 2H), 4.71 (s, 2H).
Mass 222 [M+H]+.

Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204
[2] Tetrahedron, 2018, vol. 74, # 15, p. 1908 - 1917
[3] Tetrahedron Letters, 2014, vol. 55, # 29, p. 3892 - 3895
[4] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 4, p. 477 - 479
[5] Journal of Organometallic Chemistry, 2017, vol. 851, p. 194 - 209
[6] Journal of Organometallic Chemistry, 1995, vol. 497, # 1-2, p. 73 - 80
[7] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 7, p. 2849 - 2855
[8] Journal of Organic Chemistry, 2015, vol. 80, # 17, p. 8530 - 8538
[9] Journal of Photochemistry and Photobiology A: Chemistry, 2018, vol. 360, p. 26 - 33
[10] Patent: US2009/18163, 2009, A1, . Location in patent: Page/Page column 21
[11] Yakugaku Zasshi, 1951, vol. 71, p. 256,259[12] Chem.Abstr., 1952, p. 510
[13] Tetrahedron Asymmetry, 1998, vol. 9, # 13, p. 2235 - 2244
[14] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 8, p. 965 - 970
[15] Patent: US6646122, 2003, B1, . Location in patent: Page/Page column 7-8
[16] Chemical Communications, 2009, # 33, p. 4982 - 4984
[17] Letters in Organic Chemistry, 2009, vol. 6, # 2, p. 156 - 158
[18] Tetrahedron Letters, 2013, vol. 54, # 38, p. 5211 - 5213
[19] Patent: WO2015/55994, 2015, A1, . Location in patent: Page/Page column 63
[20] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4364 - 4374
[21] Patent: WO2015/124934, 2015, A1, . Location in patent: Page/Page column 44
[22] Chemistry - An Asian Journal, 2017, vol. 12, # 2, p. 239 - 247
  • 2
  • [ 1780-17-2 ]
  • [ 5632-15-5 ]
YieldReaction ConditionsOperation in experiment
83% With phosphorus tribromide In dichloromethane at 0 - 20℃; Quinolin-2-ylmethanol 7 (6 g, 37.8 mmol) was dissolved in CH2Cl2 (60 mL). PBr3 (2.14 mL, 22.6 mmol) was carefully added at 0 °C to this solution. The mixture was allowed to return at ambient temperature and was stirred for 30 min. Water (60 mL) was then added followed by a saturated aqueous solution of K2CO3 (40 mL) to obtain a pH=8. The organic phase was washed with brine (2×30 mL), dried over magnesium sulfate, and concentrated under reduced pressure. The crude residue was purified through a silica gel column chromatography (AcOEt/MCH: 20/80). White solid; 83percent yield; mp 55 °C (dec); 1H NMR (300 MHz, DMSO) 4.86 (2H, s, CH2), 7.67 (2H, m, CHar), 7.78 (1H, m, CHar), 7.99 (2H, m, CHar), 8.40 (1H, m, CHar); 13C NMR (75 MHz, DMSO) 35.67, 122.10, 127.46, 127.54, 128.34, 129.07, 130.53, 138.37, 147.36, 157.67; HRMS (ESI) m/z calculated for C10H9NBr [M+H]+: 221.99129, found: 221.991.
68% With dibromo sulfoxide In toluene at 110℃; for 1 h; PREPARATION 302-(Bromomethyl)quinolineThe title compound of Preparation 29 (3.68 g, 23.1 mmol) was suspended in 60 ml toluene. Thionyl bromide (12.0 g, 57.8 mmol) was slowly added and the mixture was heated at 110°C for 1 h. The mixture was concentrated under reduced pressure and the residue was partitioned between water and dichloromethane. The aqueous phase was basified with potassium carbonate and extracted three times with dichloromethane. The combined organics were washed with water, brine and dried over sodium sulphate and evaporated. The residue was purified by column chromatography (ethyl acetate-hexane, 5:95) to give 3.5 g (15.8 mmol, 68percent) of the title compound as a solid. Purity 100percent.1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.72 (s, 2 H), 7.54 - 7.62 (m, 2H), 7.70 - 7.79 (m, 1 H), 7.83 (d, J=8.21 Hz, 1 H), 8.08 (d, J=8.21 Hz, 1 H),8.19 (d, J=8.60 Hz, 1 H).HPLC/MS (9 min) retention time 5.45 min.LRMS: m/z 224 (M+1).
68%
Stage #1: With dibromo sulfoxide In toluene at 110℃; for 1 h;
Stage #2: With potassium carbonate In water
The title compound of Preparation 29 (3.68 g, 23.1 mmol) was suspended in 60 ml toluene. Thionyl bromide (12.0 g, 57.8 mmol) was slowly added and the mixture was heated at 110C for 1 h. The mixture was concentrated under reduced pressure and the residue was partitioned between water and dichloromethane. The aqueous phase was basified with potassium carbonate and extracted three times with dichloromethane. The combined organics were washed with water, brine and dried over sodium sulphate and evaporated. The residue was purified by column chromatography (ethyl acetate-hexane, 5:95) to give 3.5 g (15.8 mmol, 68percent) of the title compound as a solid. Purity 100percent. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.72 (s, 2 H), 7.54 - 7.62 (m, 2 H), 7.70 - 7.79 (m, 1 H), 7.83 (d, J=8.21 Hz, 1 H), 8.08 (d, J=8.21 Hz, 1 H), 8.19 (d, J=8.60 Hz, 1 H). HPLC/MS (9 min) retention time 5.45 min. LRMS: m/z 224 (M+1).
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 38, p. 5211 - 5213
[2] Tetrahedron, 1999, vol. 55, # 41, p. 12069 - 12078
[3] Tetrahedron, 2013, vol. 69, # 44, p. 9322 - 9328
[4] Tetrahedron Asymmetry, 2009, vol. 20, # 14, p. 1672 - 1682
[5] Patent: WO2012/69175, 2012, A1, . Location in patent: Page/Page column 42-43
[6] Patent: EP2457900, 2012, A1, . Location in patent: Page/Page column 25; 26
[7] Tetrahedron Letters, 2012, vol. 53, # 35, p. 4747 - 4750
[8] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4364 - 4374
[9] Chemistry - An Asian Journal, 2017, vol. 12, # 2, p. 239 - 247
  • 3
  • [ 94-36-0 ]
  • [ 5632-15-5 ]
YieldReaction ConditionsOperation in experiment
12.6% With N-Bromosuccinimide; hydrogen bromide In tetrachloromethane Step 1
To a solution of chinaldine (14.3 g, 0.1 mmol) and N-bromosuccinimide (17.8g, 0.1 mmol)in CCl4 (150 mL) was added benzoylperoxide (2.6 g, 0.025 mol) and the mixture was heated under reflux for 4 hours.
The reaction mixture was cooled to room temperature and evaporated in vacuum.
The residue was treated with 5percent HBr solution, the precipitate was filtered offand the filtrate was treated with celite and then basified with NaHCO3solution.
The product was extracted with ether and crystallized from petrolether to yield 2-(bromomethyl)-quinoline (2.8 g, 12.6percent) as light tancrystals.
Reference: [1] Patent: US5331006, 1994, A,
  • 4
  • [ 5470-96-2 ]
  • [ 5632-15-5 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 38, p. 5211 - 5213
[2] Tetrahedron, 1999, vol. 55, # 41, p. 12069 - 12078
[3] Tetrahedron Letters, 2013, vol. 54, # 38, p. 5211 - 5213
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4364 - 4374
[5] Chemistry - An Asian Journal, 2017, vol. 12, # 2, p. 239 - 247
  • 5
  • [ 91-63-4 ]
  • [ 5632-15-5 ]
  • [ 53867-81-5 ]
Reference: [1] Carbohydrate Research, 2011, vol. 346, # 14, p. 2084 - 2090
  • 6
  • [ 4377-41-7 ]
  • [ 5632-15-5 ]
Reference: [1] Tetrahedron, 1992, vol. 48, # 22, p. 4533 - 4544
  • 7
  • [ 19499-11-7 ]
  • [ 5632-15-5 ]
Reference: [1] Chemistry - An Asian Journal, 2017, vol. 12, # 2, p. 239 - 247
  • 8
  • [ 91-63-4 ]
  • [ 100-46-9 ]
  • [ 5470-96-2 ]
  • [ 5632-15-5 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 20, p. 9939 - 9946
  • 9
  • [ 91-63-4 ]
  • [ 100-46-9 ]
  • [ 5632-15-5 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 23, p. 3036 - 3047
  • 10
  • [ 613-53-6 ]
  • [ 5632-15-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1936, vol. 526, p. 22,33
[2] Journal of the Chemical Society, 1926, p. 1303
[3] Justus Liebigs Annalen der Chemie, 1936, vol. 526, p. 22,33
[4] Journal of the Chemical Society, 1926, p. 1303
[5] Justus Liebigs Annalen der Chemie, 1936, vol. 526, p. 22,33
[6] Journal of the Chemical Society, 1926, p. 1303
[7] Justus Liebigs Annalen der Chemie, 1936, vol. 526, p. 22,33
[8] Journal of the Chemical Society, 1926, p. 1303
[9] Journal of the Chemical Society, 1955, p. 2436,2440
[10] Journal of the Chemical Society, 1951, p. 1145,1147
[11] Journal of the Chemical Society, 1951, p. 1145,1147
  • 11
  • [ 19575-07-6 ]
  • [ 5632-15-5 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 35, p. 4747 - 4750
[2] Tetrahedron, 2013, vol. 69, # 44, p. 9322 - 9328
  • 12
  • [ 62-53-3 ]
  • [ 5632-15-5 ]
Reference: [1] Journal of Organometallic Chemistry, 2017, vol. 851, p. 194 - 209
  • 13
  • [ 63430-79-5 ]
  • [ 5632-15-5 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 35, p. 4747 - 4750
  • 14
  • [ 53867-81-5 ]
  • [ 5632-15-5 ]
Reference: [1] Journal of the Chemical Society, 1951, p. 1145,1147
[2] Journal of the Chemical Society, 1951, p. 1145,1147
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