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Chemistry
Organic Building Blocks
Aryls
2-(3-Bromo-4-methoxyphenyl)acetonitrile
Chemistry
Organic Building Blocks
Aryls
Bromides Ethers Nitriles Benzene Compounds Benzene Compounds

[ CAS No. 772-59-8 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Quality Control of [ 772-59-8 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 772-59-8 ]

Product Details of [ 772-59-8 ]

CAS No. :772-59-8 MDL No. :MFCD00016391
Formula : C9H8BrNO Boiling Point : 324.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :226.07 g/mol Pubchem ID :-
Synonyms :

Calculated chemistry of of [ 772-59-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.16
TPSA : 33.02 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) : -6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.13
Log Po/w (XLOGP3) : 1.87
Log Po/w (WLOGP) : 2.52
Log Po/w (MLOGP) : 2.16
Log Po/w (SILICOS-IT) : 2.81
Consensus Log Po/w : 2.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.66
Solubility : 0.497 mg/ml ; 0.0022 mol/l
Class : Soluble
Log S (Ali) : -2.19
Solubility : 1.48 mg/ml ; 0.00653 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.88
Solubility : 0.0301 mg/ml ; 0.000133 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 772-59-8 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P312+P361+P364-P304+P340+P311-P305+P351+P338+P337+P313-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301+H311+H331-H315-H319 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 772-59-8 ]

* 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.

  • Downstream synthetic route of [ 772-59-8 ]

[ 772-59-8 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 772-59-8 ]
  • [ 774-81-2 ]
Reference： [1]Journal of the Chemical Society,1938,p. 1780,1782
[2]Journal of the Chemical Society C: Organic,1970,p. 2234 - 2238
  • 2
  • [ 772-59-8 ]
  • [ 108-94-1 ]
  • (3-Bromo-4-methoxy-phenyl)-(1-hydroxy-cyclohexyl)-acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide at -78℃;
Reference： [1]Yardley; Morris Husbands; Stack; Butch; Bicksler; Moyer; Muth; Andree; Fletcher III; James; Sielecki [Journal of Medicinal Chemistry, 1990, vol. 33, # 10, p. 2899 - 2905]
  • 3
  • [ 772-59-8 ]
  • [ 159465-27-7 ]
YieldReaction ConditionsOperation in experiment
90% With lithium aluminium tetrahydride; sulfuric acid In tetrahydrofuran for 1h; Ambient temperature;
79% With borane-THF In tetrahydrofuran at 70℃; for 2h; Cooling with ice; 15 Compound 16-2 Add 2-(3-bromo-4-methoxyphenyl)acetonitrile (16-1) (10g, 44.2mmol) to tetrahydrofuran (100mL), add BH3·THF (110mL, 110mmol)under ice bath, The temperature was raised to 70°C and reacted for 2 hours.After the reaction was completed, the reaction system was cooled to 0°C, methanol (40 mL) and concentrated hydrochloric acid (12 mL) were slowly added dropwise, and the temperature was raised to 70°C to continue the reaction for 2 hours.After cooling to room temperature, it was concentrated, and the pH was adjusted to 9 with 10% NaOH solution.It was extracted three times with ethyl acetate (50 mL), the organic phases were combined and washed three times with saturated brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (methanol/dichloromethane = 1/20, Containing 0.2% triethylamine) to obtain the target intermediate 2-(3-bromo-4-methoxyphenyl)ethane-1-amine (16-2) (8 g, yield: 79%).
Reference： [1]Shah; Izenwasser; Geter-Douglass; Witkin; Newman [Journal of medicinal chemistry, 1995, vol. 38, # 21, p. 4284 - 4293]
[2]Current Patent Assignee: JIANGSU SIMCERE PHARM - CN113493438, 2021, A Location in patent: Paragraph 0412-0417
  • 4
  • [ 6940-76-7 ]
  • [ 772-59-8 ]
  • 2-(3-bromo-4-methoxy-phenyl)-5-chloro-pentanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide In tetrahydrofuran; cyclohexane at -78 - 20℃; for 1h;
Reference： [1]Ng, Howard P.; Karen, May; Bauman, John G.; Ghannam, Ameen; Islam, Imadul; Liang, Meina; Horuk, Richard; Hesselgesser, Joseph; Snider, R. Michael; Perez, H. Daniel; Morrissey, Michael M. [Journal of Medicinal Chemistry, 1999, vol. 42, # 22, p. 4680 - 4694]
  • 5
  • [ 772-59-8 ]
  • α-(3-Bromo-4-methoxyphenyl)-4-(4-chlorophenyl)-4-hydroxy-1-piperidinepentanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: LDA / cyclohexane; tetrahydrofuran / 1 h / -78 - 20 °C 2: tetrahydrofuran; cyclohexane / 65 °C
Reference： [1]Ng, Howard P.; Karen, May; Bauman, John G.; Ghannam, Ameen; Islam, Imadul; Liang, Meina; Horuk, Richard; Hesselgesser, Joseph; Snider, R. Michael; Perez, H. Daniel; Morrissey, Michael M. [Journal of Medicinal Chemistry, 1999, vol. 42, # 22, p. 4680 - 4694]
  • 6
  • [ 772-59-8 ]
  • [ 73894-40-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 90 percent / LiAlH4, 98percent H2SO4 / tetrahydrofuran / 1 h / Ambient temperature 2: 45 percent / acetonitrile / 18 h / Heating 3: 90 percent / 99percent CF3COOH, 99percent CH3SO3H / 18 h / Heating
Reference： [1]Shah; Izenwasser; Geter-Douglass; Witkin; Newman [Journal of medicinal chemistry, 1995, vol. 38, # 21, p. 4284 - 4293]
  • 7
  • [ 772-59-8 ]
  • [ 171285-31-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / LiAlH4, 98percent H2SO4 / tetrahydrofuran / 1 h / Ambient temperature 2: 45 percent / acetonitrile / 18 h / Heating
Reference： [1]Shah; Izenwasser; Geter-Douglass; Witkin; Newman [Journal of medicinal chemistry, 1995, vol. 38, # 21, p. 4284 - 4293]
  • 8
  • [ 772-59-8 ]
  • [ 171285-34-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 90 percent / LiAlH4, 98percent H2SO4 / tetrahydrofuran / 1 h / Ambient temperature 2: 45 percent / acetonitrile / 18 h / Heating 3: 90 percent / 99percent CF3COOH, 99percent CH3SO3H / 18 h / Heating 4: 65 percent / 1,3-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole hydrate, Et3N / dimethylformamide / 48 h / Ambient temperature
Reference： [1]Shah; Izenwasser; Geter-Douglass; Witkin; Newman [Journal of medicinal chemistry, 1995, vol. 38, # 21, p. 4284 - 4293]
  • 9
  • [ 772-59-8 ]
  • 8-Bromo-3-(4-dimethylamino-butyl)-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 90 percent / LiAlH4, 98percent H2SO4 / tetrahydrofuran / 1 h / Ambient temperature 2: 45 percent / acetonitrile / 18 h / Heating 3: 90 percent / 99percent CF3COOH, 99percent CH3SO3H / 18 h / Heating 4: 65 percent / 1,3-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole hydrate, Et3N / dimethylformamide / 48 h / Ambient temperature 5: 90 percent / LiAlH4, 98percent H2SO4 / tetrahydrofuran / 2 h / Ambient temperature 6: 70 percent / 1 M BBr3 / CHCl3; CH2Cl2 / 1 h / Ambient temperature
Reference： [1]Shah; Izenwasser; Geter-Douglass; Witkin; Newman [Journal of medicinal chemistry, 1995, vol. 38, # 21, p. 4284 - 4293]
  • 10
  • [ 772-59-8 ]
  • [ 171285-38-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 90 percent / LiAlH4, 98percent H2SO4 / tetrahydrofuran / 1 h / Ambient temperature 2: 45 percent / acetonitrile / 18 h / Heating 3: 90 percent / 99percent CF3COOH, 99percent CH3SO3H / 18 h / Heating 4: 65 percent / 1,3-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole hydrate, Et3N / dimethylformamide / 48 h / Ambient temperature 5: 90 percent / LiAlH4, 98percent H2SO4 / tetrahydrofuran / 2 h / Ambient temperature
Reference： [1]Shah; Izenwasser; Geter-Douglass; Witkin; Newman [Journal of medicinal chemistry, 1995, vol. 38, # 21, p. 4284 - 4293]
  • 11
  • [ 772-59-8 ]
  • [ 93413-52-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium diisopropyl amide / -78 °C 2: H2 / Rh/Al2O3 / ethanol
Reference： [1]Yardley; Morris Husbands; Stack; Butch; Bicksler; Moyer; Muth; Andree; Fletcher III; James; Sielecki [Journal of Medicinal Chemistry, 1990, vol. 33, # 10, p. 2899 - 2905]
  • 12
  • [ 38493-59-3 ]
  • [ 772-59-8 ]
Reference： [1]Journal of the Chemical Society,1938,p. 1780,1782
[2]Journal of the Chemical Society C: Organic,1970,p. 2234 - 2238
  • 13
  • [ 97-94-9 ]
  • [ 772-59-8 ]
  • [ 33839-30-4 ]
YieldReaction ConditionsOperation in experiment
38% With potassium carbonate In hexane; dichloromethane; N,N-dimethyl-formamide at 70℃; for 5h;
38% With potassium carbonate In hexane; N,N-dimethyl-formamide at 20 - 70℃; for 5h; 15.1 N,N-Dimethylformamide (75 ml) was added to 3-bromo-4-methoxybenzyl cyanide (9.0 g, 40 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II)-dichloromethane adduct (400 mg, 0.49 mmol) and potassium carbonate (24.0 g, 174 mmol) at room temperature. Further, triethylborane (1M-n-hexane solution; 50 ml, 50 mmol) was added dropwise thereto, and the reaction mixture was stirred at 70°C for 5 hours. After the temperature of the reaction mixture was returned to room temperature, the mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic later was successively washed with water and saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. The residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (elution solvent: n-hexane/ethyl acetate=8/1-5/1) to obtain oily (3-ethyl-4-methoxyphenyl)acetonitrile (2.6 g, yield: 38%) . 1H-NMR (400MHz, CDCl3) : δ 7.11 (1H, d, J = 8.4 Hz), 7.08 (1H, s), 6.81 (1H, d, J = 8.4 Hz), 3.83 (3H, s), 3.67 (2H, s), 2.63 (2H, q, J = 7.6 Hz), 1.19 (3H, t, J = 7.6 Hz).
Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - WO2006/46593, 2006, A1 Location in patent: Page/Page column 210-211
[2]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - EP1764075, 2007, A1 Location in patent: Page/Page column 97
  • 14
  • [ 772-59-8 ]
  • [ 920-39-8 ]
  • [ 31859-25-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: isopropylmagnesium bromide With zinc dibromide In tetrahydrofuran at 0℃; for 0.25h; Stage #2: (3-bromo-4-methoxyphenyl)-acetonitrile In tetrahydrofuran; dichloromethane at -78 - 20℃; for 5h;
With zinc dibromide In tetrahydrofuran at -78 - 20℃; for 5.25h; 33.1 Isopropyl magnesium bromide-0.63M tetrahydrofuran solution (3.2 ml, 2.0 mmol) was added dropwise to a solution of zinc bromide (473 mg, 2.1 mmol) in tetrahydrofuran (2 ml) under ice-cooling. After the mixture was stirred for 15 minutes, the reaction mixture was cooled to -78°C. After 3-bromo-4-methoxybenzyl cyanide (226 mg, 1.0 mmol) and [1,1'-bis(diphenylphosphino)ferocene]dichloropalladium (II)-dichloromethane adduct (32 mg, 0.04 mmol) were added to the reaction mixture at -78°C, the temperature of the reaction mixture was raised to room temperature, and the mixture was further stirred for 5 hours. 1N-Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. The residue obtained by evaporating the solvent under reduced pressure was subjected to silica gel column chromatography (elution solvent: n-hexane/ethyl acetate=8/1-6/1) to obtain crude (3-isopropyl-4-methoxyphenyl)acetonitrile (158 mg). 1H-NMR (400MHz, CDCl3) : δ 7.12-7.11 (2H, m), 6.83 (1H , d, J = 9.2 Hz), 3.83 (3H, s), 3.69 (2H, s), 3.34-3.27 (1H, m), 1.21 (3H, d, J = 6.8 Hz), 1.20 (3H, d, J = 6.8 Hz).
Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - WO2006/46593, 2006, A1 Location in patent: Page/Page column 231-232
[2]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - EP1764075, 2007, A1 Location in patent: Page/Page column 112
  • 15
  • [ 772-59-8 ]
  • [ 33513-42-7 ]
  • [ 33839-30-4 ]
YieldReaction ConditionsOperation in experiment
With triethyl borane; potassium carbonate 26.1 (26-1) (26-1) N,N-Dimethylformamide (75 ml) was added to 3-bromo-4-methoxybenzyl cyanide (9.0 g, 40 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II)-dichloromethane adduct (400 mg, 0.49 mmol) and potassium carbonate (24.0 g, 174 mmol) at room temperature. Further, triethylborane (1M n-hexane solution, 50 ml, 50 mmol) was added dropwise thereto and the reaction mixture was stirred at 70°C for 5 hours. After the temperature of the reaction mixture was returned to room temperature, the mixture was poured into water and extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCI solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluding solvent: n-hexane/ethyl acetate=8/1-5/1) to give (3-ethyl-4-methoxyphenyl)acetonitrile (2.6 g, yield: 38%) as an oil. 1H-NMR (400MHz, CDCl3): δ 7.11 (1H, d, J = 8.4 Hz), 7.08 (1H, s), 6.81 (1H, d, J = 8.4 Hz), 3.83 (3H, s), 3.67 (2H, s), 2.63 (2H, q, J = 7.6 Hz), 1.19 (3H, t, J = 7.6 Hz).
Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - EP1806332, 2007, A1
  • 16
  • [ 5414-19-7 ]
  • [ 772-59-8 ]
  • [ 1035261-11-0 ]
YieldReaction ConditionsOperation in experiment
With sodium t-butanolate In 1-methyl-pyrrolidin-2-one; diethyl ether at 20℃; for 3h; 14.A Step A: Preparation of 4-(3-Bromo-4-methoxyphenyl)- tetrahydro-2H-pyran-4-carbonitrile; [0297] A mixture of sodium tert-butoxide (6.7 g, 70 mmol) in 100 mLNMP stirred at 00C was treated dropwise with a mixture of 2-(3-bromo-4- methoxyphenyl)acetonitrile (6.3g, 28 mmol) and l-bromo-2-(2- bromoethoxy)ethane (6.5 g, 28 mmol) in 30 mL ether. The mixture was allowed to warm to room temperature and was stirred for 3 hours, M+Na = 318/320. The mixture was quenched with 100 mL H2O carefully and the pH was adjusted to 5. The mixture was extracted with ether (3 x 100 mL). The combined organic layers were washed with H2O (3 x 50 mL) and brine (20 mL). The organic layer was then dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 10-20 % EtOAc/hexane to give 5.18 g of crude product as a yellow solid. MS m/e = 318/320 (M+Na)+.
Reference： [1]Current Patent Assignee: AMGEN INC - WO2008/76427, 2008, A2 Location in patent: Page/Page column 79-80
  • 17
  • [ 89978-72-3 ]
  • [ 143-33-9 ]
  • [ 772-59-8 ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide for 2h; 43.2; 44.2 To a solution of 2-bromo-4-(bromomethyl)-1 -methoxybenzene (2.71 g, 9.68mmol) in anhydrous dimethylsulfoxide (3OmL), under nitrogen, was added sodium cyanide (549mg, 10.6mmol). After 2 hours the reaction was poured into 5% sodium chloride (20OmL), extracted with ethyl acetate (3 x 75mL), washed with brine (10OmL), dried over magnesium sulfate, filtered and the solvent removed by evaporation under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with a solvent gradient of ethyl acetate:heptane (5:95, by volume) changing to ethyl acetate:heptane (50:50, by volume), to provide the title compound (1.45g) as an oil. 1H NMR (400 MHz, CHLOROFORM-c/) δ ppm 3.69 (s, 2 H) 3.91 (s, 3 H) 6.90 (d, J=8.40 Hz, 1 H) 7.23 - 7.27 (m, 1 H) 7.51 (d, J=2.15 Hz, 1 H). LCMS : m/z [M-CN] 198.9, 200.9.
Reference： [1]Current Patent Assignee: PFIZER INC - WO2009/69044, 2009, A1 Location in patent: Page/Page column 132
  • 18
  • [ 772-59-8 ]
  • [ 111-44-4 ]
  • [ 1035261-11-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (3-bromo-4-methoxyphenyl)-acetonitrile With sodium hydride In N,N-dimethyl-formamide for 1h; Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl-formamide for 18h; 43.3; 44.3 To a solution of 2-(3-bromo-4-methoxyphenyl)acetonitrile (500mg, 2.21 mmol) in anhydrous N,N-dimethylfornnannide (5ml_), under argon, was added sodium hydride (186mg, 4.64mmo). After stirring for one hour 2-chloroethyl ether (0.556ml_, 4.64mmol) was added and stirring was continued for 18 hours. After which time the reaction was poured into water (15OmL), extracted with ethyl acetate (3 x 75ml_), washed with brine (10OmL), dried over magnesium sulfate, filtered and the solvent removed by evaporation under reduced pressure, to provide the title compound (662mg) as an oil. LCMS : m/z [MH+] 295.2, 297.2
Reference： [1]Current Patent Assignee: PFIZER INC - WO2009/69044, 2009, A1 Location in patent: Page/Page column 132-133
  • 19
  • methyl 3-hydroxy-2-methylenebutyrate [ No CAS ]
  • [ 772-59-8 ]
  • [ 1158805-01-6 ]
YieldReaction ConditionsOperation in experiment
92% With N-Methyldicyclohexylamine; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 100℃; for 18h; Inert atmosphere; Closed tube;
With N-cyclohexyl-cyclohexanamine In ISOPROPYLAMIDE at 80℃; for 72h; 83.i (i) Methyl 2-(5-(cyanomethyl)-2-methoxybenzyl)-3-oxobutanoate N,N-dimethylacetamide (20OmL) was added to Pd-118 (1.009g) and tetrabutylammonium chloride hydrate (0.916g), followed by 2-(3-bromo-4-methoxyphenyl)acetonitrile (7g). Methyl 3-hydroxy-2-methylenebutyrate (5.64mL) and dicyclohexylamine (9.25mL) were added and the solution was heated at 800C for 3 days. The reaction mixture was diluted with EtOAc (20OmL) and extracted with water. The organic phase was dried, filtered and evaporated under reduced pressure. The crude product was purified by chromatography to afford the subtitle compound as an orange oil, 5.01g. LC-MS m/z 276 APCI +
With dichlorobis(tri-O-tolylphosphine)palladium; triethylamine In acetonitrile at 70℃; 1.1a.2 Step 2: methyl 2-(5-(cyanomethyl)-2-methoxybenzyl)-3-oxobutanoate A mixture of 2-(3-bromo-4-methoxyphenyl)acetonitrile (1.0 eq) in MeCN (0.44M), methyl 3-hydroxy-2-methylenebutanoate (2.0 eq), PdCl2(P(o-tol)3)2 (0.03 eq), TEA (2.0 eq) was stirred overnight at 70°C. The mixture was partitioned between EA/water. The organic layer was dried over Na2S04, concentrated and purified by flash chromatography on silica (eluent PE/EA = 100: l~2: 1) to give the title compound.
Reference： [1]Location in patent: experimental part Bennett, Nicholas J.; Goldby, Anne; Pringle, Rachel [Synlett, 2010, # 11, p. 1688 - 1690]
[2]Current Patent Assignee: ASTRAZENECA PLC; Sumitomo Pharma (in: Sumitomo Chemical); Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - WO2009/67081, 2009, A1 Location in patent: Page/Page column 155-156
[3]Current Patent Assignee: TSINGHUA TONGFANG CO., LTD - WO2019/236469, 2019, A1 Location in patent: Paragraph 0139; 0141
  • 20
  • [ 772-59-8 ]
  • [ 141-78-6 ]
  • [ 91348-43-5 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: (3-bromo-4-methoxyphenyl)-acetonitrile With sodium hydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Cooling with ice; Stage #2: ethyl acetate In tetrahydrofuran at 60℃; Inert atmosphere;
70% With sodium hydride In tetrahydrofuran
Reference： [1]Cai, Tong; Candler, Yolanda; Chen, Ou; He, Jie; Hills-Kimball, Katie; Shi, Wenwu; Wang, Ping; Wei, Zichao; Yang, Hanjun; Yuan, Yucheng; Zhu, Hua [Angewandte Chemie - International Edition, 2020, vol. 59, # 50, p. 22563 - 22569][Angew. Chem., 2020, vol. 132, # 50, p. 22752 - 22758,7]
[2]Liang, Zhidan; Hou, Weizhe; Du, Yunfei; Zhang, Yongliang; Pan, Yan; Mao, Deng; Zhao, Kang [Organic Letters, 2009, vol. 11, # 21, p. 4978 - 4981]
  • 21
  • [ 772-59-8 ]
  • [ 777-64-0 ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride; potassium hydroxide In methanol at 60℃; for 17h;
Reference： [1]Kirschberg, Thorsten A.; Balakrishnan, Mini; Squires, Neil H.; Barnes, Tiffany; Brendza, Katherine M.; Chen, Xiaowu; Eisenberg, Eugene J.; Jin, Weili; Kutty, Nilima; Leavitt, Stephanie; Liclican, Albert; Liu, Qi; Liu, Xiaohong; Mak, John; Perry, Jason K.; Wang, Michael; Watkins, William J.; Lansdon, Eric B. [Journal of Medicinal Chemistry, 2009, vol. 52, # 19, p. 5781 - 5784]
  • 22
  • [ 772-59-8 ]
  • [ 74-88-4 ]
  • [ 628311-33-1 ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: (3-bromo-4-methoxyphenyl)-acetonitrile With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; 1 Stepi: Synthesis of 2-(3-Bromo-4-methoxy-phenyl)-2-methyl-propionitrile (2) Stepi: Synthesis of 2-(3-Bromo-4-methoxy-phenyl)-2-methyl-propionitrile (2)NaH (3.7 g, 93 mmol) was added into THE (100 mL) slowly at 0°C, followed by I (7 g, 31 mmol). The solution was stirred at 0°C for 1 hour and then Mel (26.4 g, 186 mmol) was added. This reaction mixture was stirred at rt for overnight. Water (10 mL)was added and the mixture was extracted with EA. The organic layer was washed with brine, dried over EA and concentrated to give 2 as a colourless oil (9 g, 85%).
85% Stage #1: (3-bromo-4-methoxyphenyl)-acetonitrile With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran at 20℃; Synthesis of 2-(3-Bromo-4-methoxyphenyl)-2-methylpropionitrile NaH (3.7 g, 93 mmol) was added into THF (100 ml_) slowly at 0°C, followed by (3-Bromo-4-methoxy-phenyl)-acetonitrile (7 g, 31 mmol). The solution was stirred at 0°C for 1 hour and then Mel (26.4 g, 186 mmol) was added. This reaction mixture was stirred at rt for overnight. Water (10 ml_) was added and the mixture was extracted with EA. The organic layer was washed with brine, dried over EA and concentrated to give 2-(3-Bromo-4-methoxy-phenyl)-2-methyl-propionitrile as a colourless oil (9 g, 85%).
85% Stage #1: (3-bromo-4-methoxyphenyl)-acetonitrile With sodium hydride In tetrahydrofuran; acetonitrile at 0℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran; acetonitrile at 20℃; Synthesis of 2-(3-Bromo-4-methoxy-phenyl)-2-methyl-propionitrile NaH (3.7 g, 93 mmol) was added into THF (100 mL) slowly at 0° C., followed by (3-Bromo-4-methoxy-phenyl)-acetonitrile (7 g, 31 mmol). The solution was stirred at 0° C. for 1 hour and then MeI (26.4 g, 186 mmol) was added. This reaction mixture was stirred at rt for overnight. Water (10 mL) was added and the mixture was extracted with EA. The organic layer was washed with brine, dried over EA and concentrated to give 2-(3-Bromo-4-methoxy-phenyl)-2-methyl-propionitrile as a colourless oil (9 g, 85%).
Reference： [1]Current Patent Assignee: SANOFI - WO2014/154727, 2014, A1 Location in patent: Page/Page column 96; 97
[2]Current Patent Assignee: SANOFI - WO2014/154726, 2014, A1 Location in patent: Page/Page column 94
[3]Current Patent Assignee: SANOFI - US2014/296296, 2014, A1 Location in patent: Paragraph 0231; 0232
  • 23
  • [ 772-59-8 ]
  • [ 73348-21-7 ]
YieldReaction ConditionsOperation in experiment
98% With boron tribromide In dichloromethane at -78 - 20℃; for 14h; Inert atmosphere;
Reference： [1]Kavanagh, Madeline E.; Coyne, Anthony G.; McLean, Kirsty J.; James, Guy G.; Levy, Colin W.; Marino, Leonardo B.; De Carvalho, Luiz Pedro S.; Chan, Daniel S. H.; Hudson, Sean A.; Surade, Sachin; Leys, David; Munro, Andrew W.; Abell, Chris [Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3272 - 3302]
  • 24
  • [ 24424-99-5 ]
  • [ 772-59-8 ]
  • tert-butyl 2-(3-bromo-4-methoxyphenyl)-2-cyanoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% Stage #1: (3-bromo-4-methoxyphenyl)-acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 1.5h; Stage #2: di-<i>tert</i>-butyl dicarbonate In tetrahydrofuran at -78℃; for 16h;
Reference： [1]Iriarte, Igor; Vera, Silvia; Badiola, Eider; Mielgo, Antonia; Oiarbide, Mikel; García, Jesús M.; Odriozola, José M.; Palomo, Claudio [Chemistry - A European Journal, 2016, vol. 22, # 38, p. 13690 - 13696]
  • 25
  • [ 104-47-2 ]
  • [ 772-59-8 ]
YieldReaction ConditionsOperation in experiment
72% With N-Bromosuccinimide; palladium diacetate; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane Inert atmosphere; Sealed tube; regioselective reaction;
Reference： [1]Das, Riki; Kapur, Manmohan [Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1114 - 1126]
  • 26
  • [ 772-59-8 ]
  • [ 13291-18-4 ]
  • [ 885682-48-4 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran 109.1 (109-1) (109-1) According to a method similar to Example (42-1), from 3-bromo-4-methoxybenzylcyanide (8.7 g, 38.5 mmol) and an isopropenylmagnesium bromide-0.5M tetrahydrofuran solution (100 ml, 50 mmol), (3-isopropenyl-4-methoxyphenyl)acetonitrile was obtained (4.42 g, yield: 61%). 1H-NMR (400MHz, CDCl3): δ 7.20 (1H, dd, J = 8.6, 2.3 Hz), 7.12 (1H, d, J = 2.3 Hz), 6.86 (1H, d, J = 8.6 Hz), 5.18-5.16 (1H, m), 5.06-5.04 (1H, m), 3.84 (3H, s), 3.68 (2H, s), 2.10 (3H, t, J = 1.2 Hz).
Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - EP1806332, 2007, A1
  • 27
  • [ 772-59-8 ]
  • isopropylmagnesium bromide-0.63M tetrahydrofuran [ No CAS ]
  • [ 31859-25-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; zinc dibromide In tetrahydrofuran 42.1 (42-1) (42-1) An isopropylmagnesium bromide-0.63M tetrahydrofuran solution (3.2 ml, 2.0 mmol) was added dropwise to a solution of zinc bromide (473 mg, 2.1 mmol) in tetrahydrofuran (2 ml) under ice-cooling. After the mixture was stirred for 15 minutes, the reaction mixture was cooled to -78°C. After 3-bromo-4-methoxybenzyl cyanide (226 mg, 1.0 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II)-dichloromethane adduct (32 mg, 0.04 mmol) were added to the mixture at -78°C, the temperature of the reaction mixture was raised to room temperature and the mixture was further stirred for 5 hours. 1N Hydrochloric acid was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was subjected to silica gel column chromatography (eluding solvent: n-hexane/ethyl acetate=8/1-6/1) to give crude (3-isopropyl-4-methoxyphenyl)acetonitrile (158 mg). 1H-NMR (400MHz, CDCl3): δ 7.12-7.11 (2H, m), 6.83 (1H, d, J = 9.2 Hz), 3.83 (3H, s), 3.69 (2H, s), 3.34-3.27 (1H, m), 1.21 (3H, d, J = 6.8 Hz), 1.20 (3H, d, J = 6.8 Hz).
Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - EP1806332, 2007, A1
  • 28
  • [ 772-59-8 ]
  • [ 109-64-8 ]
  • 1-(3-bromo-4-methoxyphenyl)cyclobutane-1-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 16h;
68% With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 16h; J203.A; S59.A Step A: 1-(3-Bromo-4-methoxyphenyl)cyclobutane-1-carbonitrile. To a mixture containing 2-(3-bromo-4-methoxyphenyl)acetonitrile (4.52 g, 20 mmol) and 1,3- dibromopropane (2.23 mL, 22 mmol) in DMSO (100 mL) was added NaH (60% dispersion in mineral oil, 2.0 g, 50 mmol) portion- wise. The reaction mixture was allowed to stir for 16 h at r.t, then diluted with EtOAc: EtaO (200 mL, 1:1) and washed with water (3 x 400 mL). The combined aqueous layers were back-extracted with further EtOAc (200 mL). The combined organics were washed with saturated aqueous NaCl, concentrated and purified by ISCO flash column chromatography (120 g, 0-25% EtOAc in hexanes) to afford a colorless oil (3.65 g, 13.7 mmol, 68%).1H NMR (400 MHz, CDCI3) dH7.61 (d, J= 2.4 Hz, 1H), 7.34 (dd, J= 8.6, 2.4 Hz, 1H), 6.93 (d, J= 8.6 Hz, 1H), 3.93 (s, 3H), 2.88 - 2.78 (m, 2H), 2.66 - 2.54 (m, 2H), 2.44 (dt, J= 11.6, 8.7 Hz, 1H), 2.16 - 2.04 (m, 1H); LCMS (Method B) to = 1.10 min, no mass observed; Purity (AUC) >95%.
Reference： [1]Macdonald, Jonathan D.; Chacón Simon, Selena; Han, Changho; Wang, Feng; Shaw, J. Grace; Howes, Jennifer E.; Sai, Jiqing; Yuh, Joannes P.; Camper, Demarco; Alicie, Bethany M.; Alvarado, Joseph; Nikhar, Sameer; Payne, William; Aho, Erin R.; Bauer, Joshua A.; Zhao, Bin; Phan, Jason; Thomas, Lance R.; Rossanese, Olivia W.; Tansey, William P.; Waterson, Alex G.; Stauffer, Shaun R.; Fesik, Stephen W. [Journal of Medicinal Chemistry, 2019, vol. 62, # 24, p. 11232 - 11259]
[2]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2021/21951, 2021, A1 Location in patent: Paragraph 001111-001112; 001411-001412
  • 29
  • [ 111-24-0 ]
  • [ 772-59-8 ]
  • 1-(3-bromo-4-methoxyphenyl)cyclohexane-1-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 16h;
Reference： [1]Macdonald, Jonathan D.; Chacón Simon, Selena; Han, Changho; Wang, Feng; Shaw, J. Grace; Howes, Jennifer E.; Sai, Jiqing; Yuh, Joannes P.; Camper, Demarco; Alicie, Bethany M.; Alvarado, Joseph; Nikhar, Sameer; Payne, William; Aho, Erin R.; Bauer, Joshua A.; Zhao, Bin; Phan, Jason; Thomas, Lance R.; Rossanese, Olivia W.; Tansey, William P.; Waterson, Alex G.; Stauffer, Shaun R.; Fesik, Stephen W. [Journal of Medicinal Chemistry, 2019, vol. 62, # 24, p. 11232 - 11259]
  • 30
  • [ 772-59-8 ]
  • [ 1692-25-7 ]
  • 2-(4-methoxy-3-(pyridin-3-yl)phenyl)acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 120℃; for 1h; Inert atmosphere; Microwave irradiation;
Reference： [1]Sijm, Maarten; Sterk, Geert Jan; Caljon, Guy; Maes, Louis; de Esch, Iwan J. P.; Leurs, Rob [ChemMedChem, 2020, vol. 15, # 14, p. 1310 - 1321]
  • 31
  • [ 772-59-8 ]
  • 2,3-diacetyl-2,3-bis(3-bromo-4-methoxyphenyl)succinonitrile [ No CAS ]
  • 2,3-diacetyl-2,3-bis(3-bromo-4-methoxyphenyl)succinonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Cooling with ice 1.2: 60 °C / Inert atmosphere 2.1: 3-(N,Ndimethyloctadecylammonio) propanesulfonate capped CsPbBr3 perovskite / tetrahydrofuran; toluene / 2.5 h / 20 °C / Irradiation
Reference： [1]Cai, Tong; Candler, Yolanda; Chen, Ou; He, Jie; Hills-Kimball, Katie; Shi, Wenwu; Wang, Ping; Wei, Zichao; Yang, Hanjun; Yuan, Yucheng; Zhu, Hua [Angewandte Chemie - International Edition, 2020, vol. 59, # 50, p. 22563 - 22569][Angew. Chem., 2020, vol. 132, # 50, p. 22752 - 22758,7]

Tags: 772-59-8 synthesis path| 772-59-8 SDS| 772-59-8 COA| 772-59-8 purity| 772-59-8 application| 772-59-8 NMR| 772-59-8 COA| 772-59-8 structure

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