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Chemical Structure| 452-74-4
Chemical Structure| 452-74-4
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Product Details of [ 452-74-4 ]

CAS No. :452-74-4 MDL No. :MFCD00040940
Formula : C7H6BrF Boiling Point : -
Linear Structure Formula :- InChI Key :SLFNGVGRINFJLK-UHFFFAOYSA-N
M.W :189.02 Pubchem ID :573280
Synonyms :

Calculated chemistry of [ 452-74-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.07
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
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) : -5.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 3.08
Log Po/w (WLOGP) : 3.32
Log Po/w (MLOGP) : 3.79
Log Po/w (SILICOS-IT) : 3.4
Consensus Log Po/w : 3.18

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.45
Solubility : 0.0677 mg/ml ; 0.000358 mol/l
Class : Soluble
Log S (Ali) : -2.75
Solubility : 0.338 mg/ml ; 0.00179 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.92
Solubility : 0.0228 mg/ml ; 0.000121 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 452-74-4 ]

Signal Word:Danger Class:3
Precautionary Statements:P261-P305+P351+P338 UN#:1993
Hazard Statements:H225-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 452-74-4 ]

* 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 [ 452-74-4 ]
  • Downstream synthetic route of [ 452-74-4 ]

[ 452-74-4 ] Synthesis Path-Upstream   1~38

  • 1
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Reference: [1] Journal of Fluorine Chemistry, 2002, vol. 116, # 2, p. 173 - 179
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 8124 - 8134
[3] Patent: WO2014/144380, 2014, A1, . Location in patent: Paragraph 0541
  • 2
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Reference: [1] Journal of the Indian Chemical Society, 1944, vol. 21, p. 112,114
  • 3
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  • [ 97674-02-7 ]
  • [ 29427-48-3 ]
Reference: [1] Patent: EP1382603, 2004, A1, . Location in patent: Page 109; 110
  • 4
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  • [ 5001-96-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2293 - 2306
  • 5
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  • [ 452-74-4 ]
Reference: [1] Journal of Fluorine Chemistry, 2002, vol. 116, # 2, p. 173 - 179
  • 6
  • [ 5326-34-1 ]
  • [ 452-74-4 ]
Reference: [1] Journal of Fluorine Chemistry, 2002, vol. 116, # 2, p. 173 - 179
  • 7
  • [ 612-45-3 ]
  • [ 452-74-4 ]
Reference: [1] Journal of Fluorine Chemistry, 2002, vol. 116, # 2, p. 173 - 179
  • 8
  • [ 352-70-5 ]
  • [ 452-63-1 ]
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Reference: [1] Journal of the Indian Chemical Society, 1944, vol. 21, p. 112,114
  • 9
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Reference: [1] Justus Liebigs Annalen der Chemie, 1970, vol. 732, p. 97 - 106
  • 10
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  • [ 452-80-2 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 17, p. 7471 - 7478
  • 11
  • [ 452-74-4 ]
  • [ 452-79-9 ]
YieldReaction ConditionsOperation in experiment
13 g
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -72℃; for 1 h; Inert atmosphere
Stage #2: With iodine In tetrahydrofuran; hexane at -60 - 20℃; Inert atmosphere
j0167] (13-i) Under dry nitrogen, a solution prepared by dissolving 4-bromo-3-fluorotoluene (10 g) in THF (50 mE) was cooled to —72° C. Then, a 1.6 mol/E n-butyl lithium hexane solution (35 mE) was added at —72° C. to the solution such a rate that the inside temperature was not more than —65° C., followed by thrther stirring at —72° C. for 1 hour. A solution prepared by dissolving iodine (14.8 g) in THF (30 mE) was added at —72° C. to the resultant mixture such a rate that the inside temperature was not more than —60° C., and the temperature was slowly increased to room temperature. Then, a saturated aqueous ammonium chloride solution and hexane were added at room temperature to separate an organic layer, and the organic layer was washed with a 10percent aqueous sodium sulfite solution two times and saturated brine in that order, and then dried with sodium sulfate. The sodium sulfate was filtered off, and the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to yield 13.0 g of 3-fluoro-4-iodotoluene as a yellow liquid.
Reference: [1] Patent: US2014/275577, 2014, A1, . Location in patent: Paragraph 0166; 0167
  • 12
  • [ 452-74-4 ]
  • [ 124-41-4 ]
  • [ 95740-49-1 ]
YieldReaction ConditionsOperation in experiment
65.8% at 130℃; for 12 h; To a solution of l-bromo-2-fluoro-4-methylbenzene (1.00 g, 5.29 mmol, 1 eq) in DMSO (10 mL) was added sodium methanolate (2.86 g, 52.90 mmol, 10 eq). The mixture was stirred at 130 °C for 12 h then cooled to 25 °C. Water (50 mL) was added and the aqueous phase was extracted with ethyl acetate (50 mL*3). The combined organic phases were washed with brine (50 mL*2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Example 116B (700 mg, yield =65.8percent) was obtained as colorless oil. (0413) [0199] MR: (CDCb, 400MHz): ppm 7.40 (d, J=8.0 Hz, 1H), 6.73 (s, 1H), 6.67 (d, J=8.0 Hz, 1H), 3.89 (s, 3H), 2.33 (s, 3H).
Reference: [1] Organometallics, 2013, vol. 32, # 16, p. 4516 - 4522
[2] Patent: WO2017/214413, 2017, A1, . Location in patent: Paragraph 0198-0199
  • 13
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  • [ 544-92-3 ]
  • [ 85070-67-3 ]
YieldReaction ConditionsOperation in experiment
88% for 24 h; Heating / reflux Example 59 Preparation of 2-fluoro-4-methyIbenzonitriIeA mixture of 1 -bromo-2~fluoro-4-methylbenzene (70 g, 370 mmol) and CuCN (50 g, 555 mmol) in DMF (300 mL) was heated at reflux for 24 h. After cooling to RT, concentrated aqueous ammonia (300 mL) and diethyl ether (200 mL) were added and the mixture stirred for 1 h. The mixture was extracted with diethyl ether (3 x 200 mL). The combined organic layers were washed with brine (3 x 200 mL) and dried over sodium sulfate. Solvent was removed in vacuo to give the product (44 g, 88percent) as pale yellow solid. MS (M+H)+ 136.
Reference: [1] Organic and Biomolecular Chemistry, 2004, vol. 2, # 9, p. 1339 - 1352
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2925 - 2930
[3] Patent: WO2007/76092, 2007, A2, . Location in patent: Page/Page column 74
[4] Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 7, p. 1135 - 1139[5] Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 7, p. 1439 - 1444
[6] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 17, p. 2483 - 2486
[7] Journal of Medicinal Chemistry, 2003, vol. 46, # 17, p. 3612 - 3622
  • 14
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  • [ 557-21-1 ]
  • [ 85070-67-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 11, p. 1411 - 1415
[2] Journal of the American Chemical Society, 2001, vol. 123, # 9, p. 2107 - 2108
  • 15
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Reference: [1] Patent: US2002/52363, 2002, A1,
[2] Patent: US6358985, 2002, B1,
[3] Patent: US6358985, 2002, B1,
[4] Patent: US2002/10184, 2002, A1,
[5] Patent: US2002/52380, 2002, A1,
[6] Patent: US2002/193283, 2002, A1,
[7] Patent: US6410534, 2002, B1,
[8] Patent: US6387903, 2002, B1,
[9] Patent: US6410534, 2002, B1,
[10] Patent: US6441017, 2002, B1,
[11] Patent: US6562823, 2003, B1,
[12] Patent: US6329376, 2001, B1,
[13] Patent: US6333335, 2001, B1,
  • 16
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Reference: [1] Patent: US2002/169113, 2002, A1,
[2] Patent: US6664255, 2003, B1, . Location in patent: Page column 105; 106
  • 17
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Reference: [1] Patent: US2005/154201, 2005, A1,
  • 18
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  • [ 85070-67-3 ]
Reference: [1] Patent: US2002/22633, 2002, A1,
  • 19
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  • [ 146137-80-6 ]
Reference: [1] Patent: US6462242, 2002, B1,
  • 20
  • [ 452-74-4 ]
  • [ 57848-46-1 ]
Reference: [1] Patent: WO2011/21209, 2011, A1,
[2] Patent: US2012/101099, 2012, A1,
  • 21
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  • [ 222978-03-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2004, vol. 2, # 9, p. 1339 - 1352
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2973 - 2984
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 17, p. 3612 - 3622
[4] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2925 - 2930
[5] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 10, p. 1257 - 1260
[6] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 11, p. 1411 - 1415
[7] Journal of the American Chemical Society, 2001, vol. 123, # 9, p. 2107 - 2108
[8] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 17, p. 2483 - 2486
  • 22
  • [ 452-74-4 ]
  • [ 222978-01-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2973 - 2984
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 10, p. 1257 - 1260
[3] Patent: WO2011/21209, 2011, A1,
[4] Patent: US2012/101099, 2012, A1,
[5] Patent: WO2006/133559, 2006, A1,
  • 23
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  • [ 222978-02-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2973 - 2984
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 10, p. 1257 - 1260
  • 24
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YieldReaction ConditionsOperation in experiment
73%
Stage #1: at 90℃; for 3 h;
Stage #2: With sodium hydroxide In water
Stage #3: With hydrogenchloride In water
To a solution of l-bromo-2-fluoro-4-methyl -benzene (20.0 g, 0.10 mol) in 1:1 ratio of pyridine: water (200 mL) was added potassium permanganate (66.0 g, 0.42 mmol) portion wise at 90 °C and the reaction mixture was stirred at 90 °C over a period of 3 h. The resulting reaction mixture was allowed to reach room temperature and filtered trough celite pad. The celite pad was washed with 3N sodium hydroxide (500 mL) and water (400 mL). Then ethanol was removed under reduced pressure and residue was acidified (pH=2) with 6N hydrochloric acid to obtained white precipitate. The precipitate obtained was filtered and dried to give 4-bromo-3 -fluoro-benzoic acid as white solid (17.0 g, 73percent).
73%
Stage #1: With potassium permanganate In pyridine; water at 90℃; for 3 h;
Stage #2: With sodium hydroxide In water
Stage #3: With hydrogenchloride In water
To a solution of 1-bromo-2-fluoro-4-methyl-benzene (20.0 g, 0.10 mol) in 1:1 ratio of pyridine: water (200 mL) was added potassium permanganate (66.0 g, 0.42 mmol) portion wise at 90° C. and the reaction mixture was stirred at 90° C. over a period of 3 h.
The resulting reaction mixture was allowed to reach room temperature and filtered trough celite pad.
The celite pad was washed with 3N sodium hydroxide (500 mL) and water (400 mL).
Then ethanol was removed under reduced pressure and residue was acidified (pH=2) with 6N hydrochloric acid to obtained white precipitate.
The precipitate obtained was filtered and dried to give 4-bromo-3-fluoro-benzoic acid as white solid (17.0 g, 73percent).
28%
Stage #1: With potassium permanganate In water at 95℃; for 22 h;
Stage #2: With hydrogenchloride In water
4-Bromo-3-fluorotoluene (24.4 g, 0.128 mol) was added to a mixture of KMnO4 (24g, 0.154 mol) in water (150 ml). The mixture was heated at 95°C for 2 hrs then additional KMnO4 (24 g) was added, after a further 2 hrs at 95 °C additional KMnO4 (24 g) was added and heating was maintained at 950C for 18 hours. The hot mixture was then filtered through a pad of diatomaceous earth and washed with water. The filtrate was acidified to pH 2 with 2N HCl and the white suspension was filtered and dried to give the product (7.33 g). The filtrate was extracted with EtOAc (2 x250 ml), the organic extracts dried and evaporated in vacuo to give additional product. Combined product (7.92g, 28percent). NMR: 7.68 (d, IH), 7.74 (d, IH), 7.82-7.87 (m, IH); M/z (M-Hy 217.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 10, p. 1257 - 1260
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2973 - 2984
[3] Patent: WO2011/21209, 2011, A1, . Location in patent: Page/Page column 38
[4] Patent: US2012/101099, 2012, A1, . Location in patent: Page/Page column 13; 14
[5] Patent: WO2006/64251, 2006, A1, . Location in patent: Page/Page column 80
[6] Patent: US5856274, 1999, A,
[7] Patent: US5334753, 1994, A,
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Reference: [1] Patent: US2003/220241, 2003, A1,
[2] Patent: US2003/220241, 2003, A1,
[3] Patent: US2003/220241, 2003, A1,
[4] Patent: US2002/49217, 2002, A1,
[5] Patent: US2002/99007, 2002, A1,
[6] Patent: US6358985, 2002, B1,
[7] Patent: US6350755, 2002, B1,
[8] Patent: US6297239, 2001, B1,
[9] Patent: US6316436, 2001, B1,
[10] Patent: US6284755, 2001, B1,
[11] Patent: US6413964, 2002, B1,
  • 26
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  • [ 153556-42-4 ]
Reference: [1] Patent: US6562823, 2003, B1,
  • 27
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  • [ 101048-76-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2004, vol. 2, # 9, p. 1339 - 1352
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 14, p. 2973 - 2984
  • 28
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  • [ 101048-76-4 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 41, p. 7173 - 7176
  • 29
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  • [ 627871-16-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 2, p. 457 - 460
[2] Patent: WO2016/57834, 2016, A1,
  • 30
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YieldReaction ConditionsOperation in experiment
100% at 0 - 20℃; To a stirred solution of 4-bromo-3-fluorotoluene (10 g, 52.9 mmol) in H2SO4 (100 mL) was added [KN03] (5.34 g, 52.9 mmol) at [0°C.] After stirring overnight at room temperature, the reaction mixture was poured into ice (200 g) and extracted with EtOAc (3 x 300 mL). The organic solution was washed with brine (200 mL), dried (Na2SO4), and concentrated to give 12.35 g (100percent) of title compound as a pale yellow [OIL.APOS;H NMR (CDCIS)] : [300 MHZ No. 8. ]29 (d, [J= 6.] 30 Hz, 1H), 7.12 (d, J= 8.61 Hz, 1H), 2.60 (s, 3H).
80% at -20 - 0℃; for 0.166667 h; 1-Bromo-2-fluoro-4-methyl-5-nitrobenzene HNO3 (9 mL) was added into a solution of 1-bromo-2-fluoro-4- methylbenzene (5.35 g, 28.30 mmol) in H2SO4 (25 mL) while it was kept at -20 °C and the resulting mixture was stirred at 0 °C for 10 min. The mixture was poured into ice- water and extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3 aqueous solution and brine, dried over Na2SO4 and concentrated in vacuo to yield the product as a yellow solid (5.3g, 80 percent yield).
78% at 0 - 20℃; for 0.166667 h; To a solution of 1-Bromo-2-fluoro-4-methyl-benzene (5.35 g, 28.30 mmol) in concentrated sulfuric acid (25 ml) was added concentrated nitric acid(9 ml) dropwise while maintaining an internal reaction temperature below 20° C.
The reaction mixture was stirred at 0° C. for 10 minutes and poured into ice water.
The resulting mixture was extracted three times with ether.
The combined ether extracts were washed with brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure.
The residue was purified by flash column chromatography over silica gel eluding with 2 to 3percent ethyl acetate in hexanes give 1-Bromo-2-fluoro-4-methyl-5-nitro-benzene as a white solid (5.21g, 78percent).
1H NMR (CDCl3) d:2.60 (s, 3H), 7.11 (d, 1H, J=8.6 Hz), 8.28 (d, 1H, J=6.4 Hz).
Reference: [1] Patent: WO2003/99824, 2003, A1, . Location in patent: Page 32
[2] Patent: WO2003/99275, 2003, A1, . Location in patent: Page 65
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 2, p. 457 - 460
[4] Patent: WO2015/54572, 2015, A1, . Location in patent: Page/Page column 247
[5] Patent: US2004/224973, 2004, A1, . Location in patent: Page 21
[6] Patent: WO2016/57834, 2016, A1, . Location in patent: Paragraph 000891
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YieldReaction ConditionsOperation in experiment
90% With N-Bromosuccinimide In acetonitrile for 3 h; Reflux A solution of 4-bromo-3-fluorotoluene (21.5 g, 0.1 14 moles) in acetonitrile (200 ml) is added with N-bromosuccinimide, (NBS; 21.2 g, 0.1 19 moles). The mixture is refluxed, added with dibenzoyl peroxide (1.4 g, 0.004 moles), refluxed for 3 hour, then cooled at room temperature and extracted with water. The aqueous phase is discarded, the organic phase is washed with brine, dried over sodium sulphate and concentrated under vacuum to give an oil (27.1 g, 90percent yield).
90% With N-Bromosuccinimide In acetonitrile for 3 h; Reflux Example 1Preparation of 4-bromo-3-fluorobenzyl bromide (III)A solution of 4-bromo-3-fluorotoluene (21.5 g, 0.114 moles) in acetonitrile (200 ml) is added with N-bromosuccinimide, (NBS; 21.2 g, 0.119 moles). The mixture is refluxed, added with dibenzoyl peroxide (1.4 g, 0.004 moles), refluxed for 3 hour, then cooled at room temperature, and extracted with water. The aqueous phase is discarded, and the organic phase is washed with brine, dried over sodium sulphate, and concentrated under vacuum to give an oil (27.1 g, 90percent yield).
80% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 3.5 h; Reflux A solution of 4-bromo-3-fluorotoluene (11.34 g, 60 mmol), azobisisobutyronitrile (0.99 g, 6 mmol), and N-bromosuccinimide (11.75 g, 66 mmol) in carbon tetrachloride (60 ml) was heated to reflux for 3.5 h. The reaction mixture was cooled to room temperature and then filtered through Celite, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Isco Combiflash, 40 g, ethyl acetate:hexane = 0:100 to 100:0, gradient) to obtain the title compound (12.8 g, 80percent) as a light yellow solid. 1H-NMR (400 MHz, CDCl3) δ: 4.41 (2H, s), 7.04-7.08 (1H, m), 7.15-7.19 (1H, m), 7.49-7.54 (1H, m)
Reference: [1] Patent: WO2011/15287, 2011, A2, . Location in patent: Page/Page column 13
[2] Patent: US2011/39934, 2011, A1, . Location in patent: Page/Page column 5
[3] Patent: EP2700643, 2014, A1, . Location in patent: Paragraph 0234
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2293 - 2306
[5] Journal of Medicinal Chemistry, 2005, vol. 48, # 18, p. 5705 - 5720
[6] Patent: WO2008/51404, 2008, A2, . Location in patent: Page/Page column 67
[7] Patent: WO2004/74232, 2004, A1, . Location in patent: Page 14
[8] Patent: WO2007/69986, 2007, A1, . Location in patent: Page/Page column 92
[9] Patent: WO2007/100295, 2007, A1, . Location in patent: Page/Page column 298
[10] Patent: WO2011/99978, 2011, A1, . Location in patent: Page/Page column 41
[11] Patent: WO2015/19325, 2015, A1, . Location in patent: Page/Page column 127
[12] Patent: US2015/368278, 2015, A1, . Location in patent: Paragraph 1262
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Reference: [1] Patent: WO2005/56529, 2005, A1, . Location in patent: Page/Page column 36
[2] Patent: US2015/191483, 2015, A1, . Location in patent: Paragraph 0724-0725
[3] Patent: WO2006/133559, 2006, A1, . Location in patent: Page/Page column 29
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Reference: [1] Patent: US6333335, 2001, B1,
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  • [ 499983-13-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 18, p. 5705 - 5720
[2] Patent: WO2011/15287, 2011, A2,
[3] Patent: US2011/39934, 2011, A1,
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2293 - 2306
[5] Patent: EP2700643, 2014, A1,
[6] Patent: US2015/368278, 2015, A1,
[7] Patent: WO2006/133559, 2006, A1,
  • 35
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  • [ 170981-26-7 ]
Reference: [1] Patent: US6235747, 2001, B1,
[2] Patent: US6362195, 2002, B1, . Location in patent: Example 2
[3] Patent: WO2004/22556, 2004, A1, . Location in patent: Page 23
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Reference: [1] Patent: US2002/22642, 2002, A1,
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  • [ 74733-29-2 ]
Reference: [1] Patent: WO2014/144380, 2014, A1,
  • 38
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  • [ 1071-36-9 ]
  • [ 518070-26-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 19, p. 4470 - 4474
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Chemical Structure| 452-62-0

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Chemical Structure| 127425-73-4

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1-Bromo-4-(bromomethyl)-2-fluorobenzene

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1-Bromo-2-fluoro-4-propylbenzene

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Aryls

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2-Bromo-1-fluoro-3-methylbenzene

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1-Bromo-2-fluoro-3-methylbenzene

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3-Bromo-4-fluorotoluene

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1-Bromo-4-(bromomethyl)-2-fluorobenzene

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Bromides

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