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Chemical Structure| 19524-06-2
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Product Details of [ 19524-06-2 ]

CAS No. :19524-06-2 MDL No. :MFCD00012828
Formula : C5H5BrClN Boiling Point : -
Linear Structure Formula :- InChI Key :MPZMVUQGXAOJIK-UHFFFAOYSA-N
M.W : 194.46 Pubchem ID :88100
Synonyms :

Calculated chemistry of [ 19524-06-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.9
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.34
Log Po/w (WLOGP) : 2.65
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 2.18
Consensus Log Po/w : 1.75

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.07
Solubility : 0.164 mg/ml ; 0.000842 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 1.09 mg/ml ; 0.00562 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.86
Solubility : 0.267 mg/ml ; 0.00137 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.35

Safety of [ 19524-06-2 ]

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

Application In Synthesis of [ 19524-06-2 ]

* 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 [ 19524-06-2 ]
  • Downstream synthetic route of [ 19524-06-2 ]

[ 19524-06-2 ] Synthesis Path-Upstream   1~36

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Reference: [1] Patent: US6358971, 2002, B1,
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Reference: [1] Patent: US6358971, 2002, B1,
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Reference: [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 2, p. 630 - 639
[2] Patent: WO2009/118292, 2009, A1, . Location in patent: Page/Page column 83-84
  • 4
  • [ 75-16-1 ]
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Reference: [1] Patent: US6642237, 2003, B1, . Location in patent: Page/Page column 165-166
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Reference: [1] Synthesis, 2002, # 6, p. 749 - 752
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YieldReaction ConditionsOperation in experiment
90%
Stage #1: With potassium carbonate In dichloromethane for 2 h;
Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 16 h;
Step a: Synthesis of 4-bromo-pyridine-1 -oxideA solution of 4-bromo-pyridine hydrochloride (25 g, 128 mmol) in dichloromethane (250 mL) was treated with potassium carbonate (21 .25g, 153 mmol) and the mixture was stirred for 2 hours, followed by addition of m- chloroperbezoic acid (44g, 256 mmol). The mixture was stirred at room temperature for 16 hours, solid precipitated out, filtered and washed with ethyl acetate (2x200 ml_). The filtrate was concentrated to give solid material which was washed with ether and hexane (3x30 ml_, 1 :1 ). The solid (20g, 90percent) obtained was used as such for next step.
90%
Stage #1: With potassium carbonate In dichloromethane for 2 h;
Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 16 h;
A solution of 4-bromo-pyridine hydrochloride (25 g, 128 mmol) in dichloromethane (250 mL) was treated with potassium carbonate (21.25 g, 153 mmol) and the mixture was stirred for 2 hours, followed by addition of m-chloroperbezoic acid (44 g, 256 mmol). The mixture was stirred at room temperature for 16 hours, solid precipitated out, filtered and washed with ethyl acetate (2*200 mL). The filtrate was concentrated to give solid material which was washed with ether and hexane (3*30 mL, 1:1). The solid (20 g, 90percent) obtained was used as such for next step.
Reference: [1] Patent: WO2012/160464, 2012, A1, . Location in patent: Page/Page column 126-127
[2] Patent: US2014/155398, 2014, A1, . Location in patent: Paragraph 0767
[3] Organic Letters, 2016, vol. 18, # 14, p. 3386 - 3389
[4] Patent: US2009/239876, 2009, A1, . Location in patent: Page/Page column 24
  • 7
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  • [ 14248-50-1 ]
Reference: [1] Patent: US6509329, 2003, B1,
  • 8
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  • [ 84249-14-9 ]
Reference: [1] Patent: CN105153023, 2018, B,
  • 9
  • [ 925-90-6 ]
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  • [ 156761-88-5 ]
YieldReaction ConditionsOperation in experiment
66%
Stage #1: at -78℃; for 0.166667 h;
Stage #2: With o-tetrachloroquinone In toluene at 20℃;
Preparation 24; 4-Bromo-2-ethyl-pyridinePrepare the title compound according to the general procedure described in Journal Organic Chemistry, Vol. 50, No. 22, 1985, page 4410-4411. Slurry 4- bromopyridine hydrochloride (4.17 g, 0.021 mol) in THF (100 mL) and cool to -78 0C under nitrogen. Add ethylmagnesium bromide (15.7 mL of a 3.0 M solution in diethyl ether, 2.2 equiv.) dropwise via syringe. Stir the reaction at -78 0C for 10 minutes then remove the ice bath and allow the reaction to warm to room temperature. Quench reaction with 20percent ammonium chloride (aq) then dilute with diethyl ether. Wash organics with water, 1 N HCl (aq), then aqueous saturated sodium chloride. Dry organics over magnesium sulfate, filter and concentrate in vacuo. Redissolve the residue in toluene (100 mL) and place under nitrogen. Dissolve tetrachloro-l,2-benzoquinone (5.8 g, 1.1 equiv.) in acetic acid (50 mL) and add dropwise to the reaction. Allow reaction to stir overnight at room temperature. Make the mixture basic by adding 1 N NaOH (aq) then extract with ethyl acetate. Acidify organic layer with 1 N HCl (aq) and extract with ethyl acetate. Set organics aside. Basify the aqueous layer with 1 N NaOH (aq) and extract with DCM. Wash this organic layer with aqueous saturated sodium chloride then dry over magnesium sulfate. Filter and concentrate in vacuo to give a brown residue (2.64 g, 66percent). LCMS (ES), m/z 188 (M+l, bromide pattern).
Reference: [1] Patent: WO2006/91671, 2006, A1, . Location in patent: Page/Page column 26
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  • [ 214360-73-3 ]
  • [ 13296-04-3 ]
Reference: [1] Chemical Communications, 2007, # 45, p. 4752 - 4754
[2] Patent: WO2006/63113, 2006, A2, . Location in patent: Page/Page column 75
  • 11
  • [ 2156-71-0 ]
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Reference: [1] Organic Letters, 2010, vol. 12, # 7, p. 1516 - 1519
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Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 14, p. 2392 - 2399
  • 13
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Reference: [1] Patent: US2009/239876, 2009, A1,
  • 14
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Reference: [1] Patent: US2011/230495, 2011, A1, . Location in patent: Page/Page column 20-21
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YieldReaction ConditionsOperation in experiment
82%
Stage #1: at -20 - 0℃; for 0.5 h; Large scale
Stage #2: at 10℃; Large scale
Stage #3: With ferrous(II) sulfate heptahydrate; sulfuric acid In dichloromethane; water at 20℃; Large scale
At -20 ° C ~ -10 ° C (preferably -10 ° C),1700 g of ethyl pyruvate was dropped into 1400 g of 35percent hydrogen peroxide solution.The reaction was kept for 30 minutes and used.1400 g of 4-bromopyridine hydrochloride (Cpd 1) was added to ice water.At a temperature less than 10 ° C,Adjust the pH to 8-9 with potassium carbonateExtracted twice with 7L of dichloromethane (DCM).Dry; pour the above organic phase into a 50L reaction flask,Add 1.4 L of water to the reaction solution.4073g ferrous sulfate heptahydrate,448mL concentrated sulfuric acid,Stir at room temperature;At -10 ° C to 0 ° C (preferably -5 ° C),Add ethyl pyruvate / hydrogen peroxide solution,Continue the reaction for 4 hours; extract with 7L of water,Spin dry to give ethyl 4-bromopyridine-2-carboxylate (Cpd 2)1390g.The yield was 82percent.
Reference: [1] Patent: CN108516953, 2018, A, . Location in patent: Paragraph 0067-0071; 0076-0083
[2] Patent: CN105153023, 2018, B, . Location in patent: Paragraph 0059; 0060-0061
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Reference: [1] Inorganic Chemistry, 2016, vol. 55, # 3, p. 1089 - 1095
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  • [ 4385-76-6 ]
Reference: [1] Patent: US6399656, 2002, B1,
  • 18
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  • [ 4385-76-6 ]
Reference: [1] Synlett, 2000, # 6, p. 829 - 831
[2] Patent: CN106008565, 2016, A, . Location in patent: Paragraph 0027; 0034; 0035
  • 19
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Reference: [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 15, p. 5661 - 5674
  • 20
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  • [ 497-19-8 ]
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Reference: [1] Patent: US6174901, 2001, B1,
  • 21
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  • [ 1692-15-5 ]
Reference: [1] Inorganic Chemistry, 2001, vol. 40, # 22, p. 5536 - 5540
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YieldReaction ConditionsOperation in experiment
32%
Stage #1: With sodium hydrogencarbonate In dichloromethane; water
Stage #2: With sulfuric acid; iron(II) sulfate In dichloromethane; water
Stage #3: With dihydrogen peroxide In dichloromethane; water at -10℃; for 0.25 h;
Methyl 4-bromopyridine-2-carboxylate (147) <n="201"/>A solution of 4-bromopyridine hydrochloride (595 mg, 3.06 mmol) in DCM(20 mL) was washed with aqueous NaHCO3 (2 x 20 mL), dried (MgSO4) and filtered. The filtrate was made up to 45 mL by the addition of more DCM, then water (3 mL) was added, followed by iron(II) sulphate heptahydrate (8.51 g, 30.6 mmol) and cone. H2SO4 (0.95 mL, 9.18 mmol). In a separate flask, methyl pyruvate (4.15 mL, 46 mmol) was treated with hydrogen peroxide (3.5 mL, 30.6 mmol, 30percent solution in water) at -10°C, then this solution was added to the DCM/water mixture at -10°C with vigorous stirring. After 15 minutes, the reaction was diluted with iced water (100 mL) and extracted into DCM (4 x 20 mL). The combined DCM phases were dried (MgSO4) and removed in vacuo. The title compound was obtained after sequential column chromatography (gradient elution - 10-40percent EtOAc in heptane with 0.5percent triethylamine, then repeating with 0-20percent EtOAc in heptane with 0.5percent triethylamine). Yield: 211 mg (32percent). LC/MS tv 0.98 min.MS(ES+) m/z 218, 216 (M+H).
32%
Stage #1: With water; sodium hydrogencarbonate In dichloromethane
Stage #2: With sulfuric acid; dihydrogen peroxide; iron(II) sulfate In dichloromethane; water at -10℃; for 0.25 h;
Methyl 4-bromopyridine-2-carboxylate (147); A solution of 4-bromopyridine hydrochloride (595 mg, 3.06 mmol) in DCM(20 mL) is washed with aqueous NaHCO3 (2 x 20 mL), dried (MgSO4) and filtered. The filtrate is made up to 45 mL by the addition of more DCM, then water (3 mL) is added, followed by iron(II) sulphate heptahydrate (8.51 g, 30.6 mmol) and cone. H2SO4 (0.95 mL, 9.18 mmol). In a separate flask, methyl pyruvate (4.15 mL, 46 mmol) is treated with hydrogen peroxide (3.5 mL, 30.6 mmol, 30percent solution in water) at -10°C, then this solution is added to the DCM/water mixture at -10°C with vigorous stirring. After 15 minutes, the reaction is diluted with iced water (100 mL) and extracted into DCM (4 x 20 mL). The combined DCM phases are dried(MgSO4) and removed in vacuo. The title compound is obtained after sequential column chromatography (gradient elution - 10-40percent EtOAc in heptane with 0.5percent triethylamine, then repeating with 0-20percent EtOAc in heptane with 0.5percent triethylamine). EPO <DP n="290"/>Yield: 211 mg (32percent). LC/MS tx 0.98 min. MS(ES+) m/z 218, 216 (M+H).
32%
Stage #1: With sodium hydrogencarbonate In dichloromethane; water
Stage #2: With sulfuric acid; dihydrogen peroxide; iron(II) sulfate In dichloromethane; water at -10℃; for 0.25 h;
Synthesis of Compound R5; Methyl 4-bromopyridine-2-carboxylate (147); A solution of 4-bromopyridine hydrochloride (595 mg, 3.06 mmol) in DCM(20 mL) is washed with aqueous NaHCO3 (2 x 20 mL), dried (MgSO4) and filtered. The filtrate is made up to 45 mL by the addition of more DCM, then water (3 mL) is added, followed by iron(II) sulphate heptahydrate (8.51 g, 30.6 mmol) and cone. H2SO4 (0.95 mL, 9.18 mmol). In a separate flask, methyl pyruvate (4.15 mL, 46 mmol) is treated with hydrogen peroxide (3.5 mL, 30.6 mmol, 30percent solution in water) at -10°C, then this solution is added to the DCM/water mixture at -10°C with vigorous stirring. After 15 minutes, the reaction is diluted with iced water (100 mL) and extracted into DCM (4 x 20 mL). The combined DCM phases are dried (MgSO4) and removed in vacuo. The title compound is obtained after sequential column chromatography (gradient elution - 10-40percent EtOAc in heptane with 0.5percent triethylamine, then repeating with 0-20percent EtOAc in heptane with 0.5percent triethylamine). EPO <DP n="290"/>Yield: 211 mg (32percent).LC/MS tx 0.98 min.MS(ES+) m/z 218, 216 (M+H).
Reference: [1] Patent: WO2007/89669, 2007, A2, . Location in patent: Page/Page column 199-200
[2] Patent: WO2008/57469, 2008, A1, . Location in patent: Page/Page column 288-289
[3] Patent: WO2008/57468, 2008, A1, . Location in patent: Page/Page column 288-289
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Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6586 - 6596
[2] Organic Letters, 2008, vol. 10, # 18, p. 4109 - 4112
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YieldReaction ConditionsOperation in experiment
73% With tetrakis(triphenylphosphine) palladium(0); cetyltrimethylammonim bromide; potassium carbonate; sodium hydroxide In water at 80℃; for 0.5 h; Inert atmosphere; Micellar solution; Microwave irradiation; Green chemistry General procedure: In a 5 mL MW vial, purged with Argon for 15 min, CTAB (219 mg, 0.6 mmol), K2CO3 (278 mg, 2 mmol), 2- or 3-thiopheneboronic acid (256 mg, 2 mmol) and Pd catalyst (0.025 mmol) were introduced. The vial was purged for further 5 min and 4 mL of degassed water was added. The proper bromopyridine isomer (158 mg, 1 mmol) was added, and in the case of a 4-bromopyridine hydrocloride, NaOH (powder, 44 mg, 1.1 mmol) was added to release the pyridine in solution as a free base. The use of only one more additional equivalent of K2CO3 was not enough to make the 4-bromopyridine hydrocloride able to react considerably. The mixture was stirred and sonicated to obtain a homogeneous solution that was introduced into a pre-heated oil bath for 24 h or reacted in a MW reactor for 30 min at the proper temperature. When the starting material was consumed, the reaction was diluted with further 5 mL of water and extracted with ethyl acetate (3 5ml). For comparison a few solvents were used: CH2Cl2 (5x5mL) or Et2O (2-3x5ml) and EtOAc (2-3x5ml), with comparable efficiencies. The organic layers were then collected, dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by flash chromatography of the crude residue afforded the desired products 2-7. Yields of isolated products are based on the starting pyridine.
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 40, p. 10380 - 10386
[2] Advanced Functional Materials, 2010, vol. 20, # 1, p. 105 - 110
[3] Dyes and Pigments, 2017, vol. 137, p. 468 - 479
[4] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 16, p. 3340 - 3349
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  • [ 73564-69-9 ]
Reference: [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2012, vol. 67, # 2, p. 103 - 106
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  • [ 73564-69-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 18, p. 2275 - 2280
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 18, p. 2275 - 2280
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Reference: [1] Dalton Transactions, 2014, vol. 43, # 16, p. 6100 - 6107
[2] Inorganic Chemistry, 2014, vol. 53, # 14, p. 7591 - 7598
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Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 14, p. 2519 - 2525
[2] Patent: US2012/71461, 2012, A1,
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  • [ 197007-87-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 10, p. 1341 - 1346
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  • [ 99163-12-9 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 23, p. 4985 - 4992
[2] Chemistry - A European Journal, 2017, vol. 23, # 42, p. 10017 - 10022
[3] Angewandte Chemie - International Edition, 2010, vol. 49, # 22, p. 3757 - 3761
[4] Green Chemistry, 2018, vol. 20, # 9, p. 1975 - 1980
[5] Molecules, 2003, vol. 8, # 7, p. 556 - 564
[6] Patent: US6548494, 2003, B1,
[7] Chemical Communications, 2008, # 24, p. 2794 - 2796
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  • [ 208190-04-9 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With sodium carbonate In water; toluene at 0 - 20℃; Inert atmosphere
Stage #2: With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 85℃; for 18 h; Inert atmosphere
A mixture of 4-bromopyridine hydrochloride 15 (2.00 g, 10.3 mmol, 1.0 equiv) in water (16 ml) and toluene (22 ml) was cooled to 0 °C and a solution of Na2CO3 (2.51 g, 23.8 mmol, 2.3 equiv) in water (26 ml) was added. After warming to rt, 3-formylphenylboronic acid 16 (1.62 g, 10.8 mmol, 1.04 equiv) and Pd(PPh3)4 (0.600 g, 0.515 mmol, 0.05 equiv) were added and the reaction mixture was stirred at 85 °C for 18 h. Then, the cooled solution was diluted with CH2Cl2 (40 ml) and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2 × 16 ml) and the combined organic layers were dried over MgSO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (n-hexane/EtOAc 4:1 → 1:4, v/v) to obtain 17 as a white solid (1.77 g, 94percent); mp: 34–36 °C; IR (KBr): ν˜ ν˜ = 3440, 3025, 1689, 1582, 1379, 1188, 789, 690, 653 cm−1; 1H NMR (400 MHz, CDCl3): δ = 7.51–7.53 (m, 2H), 7.63–7.67 (m, 1H), 7.87–7.94 (m, 2H), 8.12–8.13 (m, 1H), 8.68–8.70 (m, 2H), 10.08 (s, 1H); 13C NMR (100 MHz, CDCl3): δ = 121.7, 127.9, 130.0, 130.5, 132.9, 137.2, 139.3, 147.0, 150.6, 191.8; ESI-HRMS m/z calcd for C12H9NO: 206.05764 [M+Na]+, 389.12605 [2M+Na]+, found: 206.05779, 389.12615
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 21, p. 6465 - 6481,17
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  • [ 927-74-2 ]
  • [ 192643-83-7 ]
Reference: [1] Australian Journal of Chemistry, 2008, vol. 61, # 12, p. 930 - 940
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  • [ 440112-20-9 ]
YieldReaction ConditionsOperation in experiment
62%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran for 0.666667 h;
Stage #2: With zinc(II) chloride In tetrahydrofuran at -78 - 20℃;
Stage #3: for 2 h; Reflux
4-bromopyridine hydrochloride (l-BA-2, 1 g, 5.14 mmol) was dissolved in 5.1 mL of THF and the resulting solution was cooled to -78 °C. LDA (10.28 mL of a 1 M solution in THF) was added over 10 minutes and the reaction mixture became brown. After stirring for 30 minutes, ZnC . (10.3 mL of a 0.5 M solution in THF) was added over 10 minutes and the resulting mixture was stirred for 10 minutes and then allowed to warm to rt. Iodobenzene (0.229 mL, 2.06 mmol) and Pd(PPli3)4 (593 mg, 0.514 mmol) were added and the resulting mixture was stirred under reflux for 2 h. The reaction mixture was diluted with aqueous saturated ammonium chloride and extracted with ethyl acetate. The organic phase was dried over a2S04 and 8576.98-304 evaporated .The residue was purified by silica column (hexane:EtOAc) to give 4-bromo-3-phenylpyridine (2-BA-2, 741 mg, 62percent); LCMS: 234.0 m/z (M+H)+.
Reference: [1] Patent: WO2011/79114, 2011, A1, . Location in patent: Page/Page column 113; 114
[2] Synlett, 2002, # 5, p. 808 - 810
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  • [ 579476-63-4 ]
Reference: [1] Patent: WO2009/118292, 2009, A1,
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  • [ 191602-60-5 ]
Reference: [1] Organic Process Research and Development, 2003, vol. 7, # 3, p. 436 - 445
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