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[ CAS No. 1679-18-1 ] {[proInfo.proName]}

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Chemical Structure| 1679-18-1
Chemical Structure| 1679-18-1
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Product Details of [ 1679-18-1 ]

CAS No. :1679-18-1 MDL No. :MFCD00039137
Formula : C6H6BClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CAYQIZIAYYNFCS-UHFFFAOYSA-N
M.W : 156.38 Pubchem ID :74299
Synonyms :

Calculated chemistry of [ 1679-18-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.28
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.45
Log Po/w (WLOGP) : 0.02
Log Po/w (MLOGP) : 0.88
Log Po/w (SILICOS-IT) : -0.08
Consensus Log Po/w : 0.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.24 mg/ml ; 0.00792 mol/l
Class : Soluble
Log S (Ali) : -1.91
Solubility : 1.94 mg/ml ; 0.0124 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.89
Solubility : 2.01 mg/ml ; 0.0129 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 1679-18-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1679-18-1 ]

* 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 [ 1679-18-1 ]
  • Downstream synthetic route of [ 1679-18-1 ]

[ 1679-18-1 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 1679-18-1 ]
  • [ 5957-96-0 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 11, p. 1128 - 1133
  • 2
  • [ 1899-24-7 ]
  • [ 1679-18-1 ]
  • [ 34035-03-5 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 8, p. 2273 - 2277
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 19, p. 2681 - 2683
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 10, p. 2481 - 2486
  • 3
  • [ 1679-18-1 ]
  • [ 67-68-5 ]
  • [ 16687-61-9 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 887 - 892
  • 4
  • [ 1679-18-1 ]
  • [ 6011-14-9 ]
  • [ 140-53-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 5
  • [ 464192-28-7 ]
  • [ 1679-18-1 ]
  • [ 721920-84-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7216 - 7221
  • 6
  • [ 1679-18-1 ]
  • [ 26905-02-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1731 - 1735
  • 7
  • [ 1298131-29-9 ]
  • [ 1679-18-1 ]
  • [ 20026-96-4 ]
  • [ 1298131-49-3 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 14, p. 4282 - 4284
  • 8
  • [ 108-43-0 ]
  • [ 1679-18-1 ]
  • [ 6842-62-2 ]
YieldReaction ConditionsOperation in experiment
84% With copper diacetate; triethylamine In dichloromethane at 0℃; for 6 h; Molecular sieve General procedure: To a solution ofphenol (1a-j) (1.0 mmol) and phenylboronicacid (2-5) (2mmol) in dry CH2Cl2 (5 ml) were added powdered activated4 Å molecular sieves (1.0 g), catalyst Cu(OAc)2 (1.0 mmol)and Et3N (5 mmol). The mixture was cooled to 0 °C and stirred for 6hours under air atmosphere. The reaction was quenched with an excess of n-hexane and precipitated catalyst andmolecular sieves were separated by filtration. The filtrate was evaporatedunder vacuum and the residue was purified by flash chromatography to affordpure product (6a-p).
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 30, p. 4185 - 4188
  • 9
  • [ 1679-18-1 ]
  • [ 5324-13-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2009, vol. 351, # 10, p. 1567 - 1574
  • 10
  • [ 1679-18-1 ]
  • [ 583-53-9 ]
  • [ 21711-56-8 ]
YieldReaction ConditionsOperation in experiment
19.5 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 5 h; Inert atmosphere Under a nitrogen stream1,2-dibromobenzene (20.0 g, 84.78 mmol),4-chlorophenyl boronic acid (30.49 g, 194.99 mmol), Pd (PPh3) 4 (4.89 g, 4.24 mmol) and K2CO3 (28.10 g, 203.33 mmol) were mixed with 150 ml of toluene, 150 ml of H2O and 150 ml of ethanol And the mixture was stirred at 100 degree For 5 hours. After completion of the reaction, the mixture was extracted with methylene chloride, concentrated under reduced pressure, and 19.5 g of a-1 was obtained by column chromatography.
19.5 g With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); DavePhos In ethanol; water; toluene at 100℃; for 5 h; Inert atmosphere Under a stream of nitrogen 1,2dibromobenzene(20.0 g, 84.78 mmol), 4chlorophenylboronic acid (30.49 g, 194.99 mmol),Pd (PPh3) 4 (4.89 g, 4.24 mmol), K2CO3 (28.10 g, 203.33 mmol) in a 150 ml Toluene, 150ml of H2O, the solvent put into a150ml of ethanol are mixed and stirred at 100 ° C for 5 hours. After completion of the reaction, and extracted with methylenechloride and concentrated under reduced pressure to give the a-1 19.5 g purified by column chromatography
Reference: [1] Patent: KR2015/103949, 2015, A, . Location in patent: Paragraph 0055-0057
[2] Patent: KR2016/104607, 2016, A, . Location in patent: Paragraph 0055-0057
  • 11
  • [ 589-87-7 ]
  • [ 1679-18-1 ]
  • [ 23055-77-8 ]
Reference: [1] Catalysis Communications, 2015, vol. 69, p. 11 - 15
[2] Patent: WO2006/120859, 2006, A1, . Location in patent: Page/Page column 44; 54
[3] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 14, p. 2744 - 2748
  • 12
  • [ 1679-18-1 ]
  • [ 14752-66-0 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 14, p. 2980 - 2983
  • 13
  • [ 583-55-1 ]
  • [ 1679-18-1 ]
  • [ 179526-95-5 ]
YieldReaction ConditionsOperation in experiment
90% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 4 h; Heating To a solution of 1-bromo-2-iodobenzene (30 g, 106 mmol) and (4-chlorophenyl) boronic acid (16.9 g, 108.6 mmol) in dioxaneAfter the addition, a 2M potassium carbonate aqueous solution (100 ml) was added, and tetrakis triphenylphosphinopalladium (2.45 g, 2 molpercent) was addedAnd the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature and the reaction was terminated, a potassium carbonate solutionAnd then layer separation was performed. After removal of the solvent, the product was subjected to column chromatography with hexane to obtain Compound A1, a white solid (25.3 g, 90percent)
Reference: [1] Patent: KR2017/41159, 2017, A, . Location in patent: Paragraph 0274-0276
[2] Organic Letters, 2015, vol. 17, # 2, p. 386 - 389
[3] Organic Letters, 2013, vol. 15, # 24, p. 6186 - 6189
[4] Advanced Synthesis and Catalysis, 2018, vol. 360, # 16, p. 3049 - 3054
[5] Chemical Communications, 2014, vol. 50, # 17, p. 2193 - 2195
[6] Chemical Communications, 2014, vol. 50, # 36, p. 4686 - 4689
[7] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1220 - 1227
[8] Angewandte Chemie - International Edition, 2016, vol. 55, # 21, p. 6319 - 6323[9] Angew. Chem., 2016, vol. 128, # 21, p. 6427 - 6431,5
[10] Angewandte Chemie - International Edition, 2017, vol. 56, # 4, p. 1125 - 1129[11] Angew. Chem., 2017, vol. 129, p. 1145 - 1149,5
  • 14
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  • [ 179526-95-5 ]
YieldReaction ConditionsOperation in experiment
71% With sodium carbonate In water; tolueneInert atmosphere; Reflux Sodium carbonate (19.8 g, 186.81 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.05 g, 0.90 mmol) were added to a solution of 1,2-dibromobenzene (12.8 ml, 105.98 mmol) and 4-chlorophenylboronic acid (14.1 g, 90.08 mmol) in toluene (170 ml) and water (80 ml). The mixture was purged with nitrogen and heated at reflux overnight. The reaction mixture was allowed to cool to room temperature, and partitioned between saturated aq. NH4Cl and ethyl acetate (500 ml). The organic layer was dried over MgSO4, filtered and the volatiles were evaporated under reduced pressure to give a residue. The residue was purified by column chromatography (ISCO, 330 g silica gel column, eluting with 100percent hexanes) to give the title product (17.0 g, yield: 71percent).1H NMR (400 MHz, DMSO-d6) δ ppm 7.34 (td, 1H) 7.37-7.45 (m, 3H) 7.45-7.50 (m, 1H) 7.50-7.56 (m, 2H) 7.75 (d, 1H).GC-MS: 268 [M]
Reference: [1] Patent: US2012/35134, 2012, A1, . Location in patent: Page/Page column 7; 34
[2] Patent: US5739166, 1998, A,
  • 15
  • [ 31928-44-6 ]
  • [ 1679-18-1 ]
  • [ 179526-95-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 35, p. 10276 - 10279[2] Angew. Chem., 2015, vol. 127, # 35, p. 10414 - 10418,5
  • 16
  • [ 1679-18-1 ]
  • [ 557-21-1 ]
  • [ 126747-14-6 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 9, p. 1711 - 1714
  • 17
  • [ 76-09-5 ]
  • [ 1679-18-1 ]
  • [ 18107-18-1 ]
  • [ 517920-59-1 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: at 40℃; for 2 h;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; 1,4-dioxane; hexane; water at 40℃; for 2 h;
To a 10 mL reaction tube equipped with a magnet was added 0.4 mg (0.8 mmol) of 4-chlorophenylboronic acid, 0.4 mL (0.8 mmol) of trimethylsilyl diazomethane (2 M n-hexane solution), 1 mL of toluene was added to the system, The stopper was stoppered and reacted on an electromagnetic heating stirrer at 40 ° C for 2 hours.Followed by addition of 71 mg (0.6 mmol) of pinacol (dissolved in 1 mL of 1,4-dioxane), 0.3 mL of tetrabutylammonium fluoride (1 M tetrahydrofuran solution) and 200 uL of water at 40 ° C, To continue for 2 hours.After completion of the reaction, the organic solvent was removed by a rotary evaporator and purified by column chromatography4-chlorobenzyl boronic acid pinacol ester, its structure is as follows:The compound was a colorless liquid in a yield of 85percent with the following NMR data:
Reference: [1] Patent: CN105884808, 2016, A, . Location in patent: Paragraph 0076; 0077; 0078; 0079; 0080; 0081
  • 18
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  • [ 167218-30-6 ]
Reference: [1] Patent: JP5703394, 2015, B2,
  • 19
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  • [ 1679-18-1 ]
  • [ 434941-55-6 ]
Reference: [1] Patent: WO2014/72903, 2014, A1, . Location in patent: Page/Page column 42
[2] Patent: WO2004/762, 2003, A2, . Location in patent: Page 38
  • 20
  • [ 1679-18-1 ]
  • [ 183208-35-7 ]
  • [ 918516-27-5 ]
YieldReaction ConditionsOperation in experiment
92% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In Dimethyl ether; waterReflux General procedure: Procedure: 5-bromo-1 H-pyrrolo[2,3-b]pyridine (2 g, 10.2 mmol, 1.0 eq.) , K2C03(2.8 g, 20.3 mmol, 2 eq.) and (4-chlorphenyl)boronic acid (1.8 g, 1 1.2 mmol, 1.1 eq.) was suspended in DME/H20 (30 ml, 4:1 ) and degassed with argon. Pd(PPh3)4(587 mg,508 μηηοΙ, 0.05 eq.) was added and the reaction mixture was heated under reflux until complete consumption of the starting material. The resulting solution was passed through a Celite pad, diluted with EtOAc and washed with water. The combined organic layers were dried over Na2S04and the solvent was evaporated under reduced pressure. The crude product was purified via flash chromatography (Si02, nHex/EtOAc 6:4).Yield: 2.23 g, 9.4 mmol, 92percent (white solid).TLC: PE/EtOAc 1 :11H NMR (DMSO-de,200 MHz, ppm): δ 1 1.76 (s, 1 H), 8.51 (d, J = 2.1 Hz, 1 H), 8.20 (d, J = 1 .9 Hz, 1 H), 7.72 (d, J = 8.5 Hz, 2H), 7.57 - 7.43 (m, 3H), 6.50 (dd, J = 3.2, 1.7 Hz, 1 H).;13C NMR (DMSO-d6, 50 Hz, ppm): δ 148.2, 141 .4, 138.0, 131.7, 128.9, 128.6, 127.1 , 126.9, 126.1 , 1 19.7, 100.2.
76% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane at 130℃; for 0.5 h; Inert atmosphere; Microwave irradiation 5-Bromo-7-azaindole (6e) (1.0 g, 5.0 mmol) and (4-chlorophenyl)boronic acid (6f) (954 mg, 6.2 mmol) were dissolved in 1,2-dimethoxyethane (28 mL). A solution of potassium carbonate (844 mg, 6.2 mmol) in water (8.0 mL) was then added. The resulting mixture was purged with argon for 5 min, followed by addition of bis(triphenylphosphine)dichloropalladium(II) (356 mg, 0.5 mmol). The reaction mixture was then reacted at 130 °C for 30 min under microwave irradiation. The volatiles were then removed under reduced pressure and the crude residue diluted with water (30 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic layer was dried over sodium sulphate, filtered, and the resulting filtrate evaporated in vacuo to give a crude solid that was purified using flash column chromatography to afford compound 6b (875 mg, 76percent) as a light-brown crystalline solid.
4.2 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 85 - 90℃; for 3 h; A 250 ml round bottom flask fitted with a mechanical stirrer, reflux condenser, thermometer socket was charged 5-bromoazaindole (10gm) of Formula VII, 4- chlorophenyl boronic acid (7.1gm) of Formula VIII in 1,4-dioxane (lOOmi) at room temperature and stirred for I 0mm. To the reaction mass aqueous potassium carbonate(10.5gm dissolved in 40m1 water), Pd(PPh3)4 was charged and heated to 85°C to 90°C for 3hr. After completion of the reaction cooled the temperature to 55°C to 60°C and separated organic and aqueous layers and followed by cooling the organic layer to 0°C to 5°C and stirred for lhr to precipitate solid compound. The precipitated solid was isolated by filtration, washed with n-heptane (30m1) to get crude compound.Yield: 7.2 gmPurity by HPLC: 94.8percentFormula A by HPLC: 0:1percentPurification of Formula IX:A 250 ml round bottom flask fitted with a mechanical stirrer, reflux condenser, thermometer socket was charged above obtained crude product (7.2gm) and tetrahydrofuran (1 lOmi) at room temperature and heated to 65°C for 1 1w, then distilled the tetrahydrofuran till the reaction mass volume 3 5-40 ml in the flask. Then the reaction mass temperature was cooled to room temperature and followed by 0°C to 5°C and allowed to stir for 1 hr. The precipitated solid was isolated by filtration, washed with n5 heptane (15m1) to get cream color solid. Same purification was repeated once again toobtaine pure compound of Formula IX.Yield: 4.2 gmPurity by HPLC: 99.9percentFormula A by HPLC: 0.02percent
Reference: [1] Patent: WO2018/134254, 2018, A1, . Location in patent: Page/Page column 35; 36; 79; 80
[2] Tetrahedron Letters, 2012, vol. 53, # 32, p. 4161 - 4165
[3] Patent: WO2015/75749, 2015, A1, . Location in patent: Page/Page column 43; 44
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9470 - 9489
  • 21
  • [ 1679-18-1 ]
  • [ 918516-27-5 ]
Reference: [1] Patent: WO2012/10538, 2012, A2,
[2] Patent: WO2012/10538, 2012, A2,
[3] Patent: WO2012/10538, 2012, A2,
[4] Patent: WO2012/10538, 2012, A2,
[5] Patent: US2012/22258, 2012, A1,
[6] Patent: US2012/22258, 2012, A1,
[7] Patent: US2012/22258, 2012, A1,
[8] Patent: US2012/22258, 2012, A1,
  • 22
  • [ 1679-18-1 ]
  • [ 1228780-72-0 ]
Reference: [1] Patent: WO2016/24230, 2016, A1,
  • 23
  • [ 854952-58-2 ]
  • [ 1679-18-1 ]
  • [ 1240963-55-6 ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24 h; Inert atmosphere; Reflux Round bottom flask was charged with 9-Phenyl-9H-carbazole-3-boronic acid 15g (52.25mmol), 4-chloro-Phenylboronicacid8.98g (57.47mmol) and the mixture of toluene (174ml) and the mixture was then dissolved in 21.66g of potassium carbonate (156.74 mmol) was added to a stirred aqueous solution of dissolved 87ml. Followed by adding thereto tetrakis triphenylphosphine palladium 1.20g (1.04mmol) was stirred and refluxed for 24 hours under a nitrogen atmosphere. After the end of the reaction the extract was concentrated to dryness and extracted with ethyl acetate and filtered through a magnesium sulfate, and the filtrate under reduced pressure. The product n- hexane / dichloromethane (6: 4 by volume) was purified by a silica gel column chromatography to give the intermediate (I) as 16.13g (85percent yield).
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24 h; Inert atmosphere; Reflux Round bottom flask was charged with 9-Phenyl-9H-carbazole-3-boronic acid 15g (52.25mmol), 4-chloro-Phenylboronicacid 8.98g dissolved in an aqueous solution of potassium carbonate 21.66g (156.74mmol) was dissolved was added to (57.47mmol) in toluene (174ml) into theIt was added to 87ml and stirred. Here tetrakistriphenylphosphine palladium was added to 1.20g (1.04mmol) of nitrogen atmosphere It was stirred under reflux for 24 hours under a group. After completion of the reaction, magnesium sulfate, the extract was then extracted with ethyl acetateIt was dried, filtered and concentrated under reduced pressure to the filtrate. Silica gel with: a product n- hexane / dichloromethane (volume ratio 4 6)The desired compound was purified by column chromatography of the intermediate (I) to give a 16.13g (85percent yield).
Reference: [1] Patent: KR2016/12846, 2016, A, . Location in patent: Paragraph 0207; 0208; 0209
[2] Patent: KR2016/22081, 2016, A, . Location in patent: Paragraph 0454; 0455; 0456; 0457
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  • [ 1329489-84-0 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2040 - 2047
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