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[ CAS No. 153624-38-5 ] {[proInfo.proName]}

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Chemical Structure| 153624-38-5
Chemical Structure| 153624-38-5
Structure of 153624-38-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 153624-38-5 ]

CAS No. :153624-38-5 MDL No. :MFCD01632198
Formula : C10H15BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :YZSPHVWALUJQNK-UHFFFAOYSA-N
M.W : 178.04 Pubchem ID :2773472
Synonyms :

Calculated chemistry of [ 153624-38-5 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 55.65
TPSA : 40.46 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) : -5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.42
Log Po/w (WLOGP) : 0.56
Log Po/w (MLOGP) : 1.56
Log Po/w (SILICOS-IT) : 0.55
Consensus Log Po/w : 1.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.61
Solubility : 0.435 mg/ml ; 0.00244 mol/l
Class : Soluble
Log S (Ali) : -2.91
Solubility : 0.218 mg/ml ; 0.00122 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.545 mg/ml ; 0.00306 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 153624-38-5 ]

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

Application In Synthesis of [ 153624-38-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 153624-38-5 ]

[ 153624-38-5 ] Synthesis Path-Downstream   1~80

  • 1
  • [ 5337-09-7 ]
  • [ 153624-38-5 ]
  • [ 192822-42-7 ]
  • 11
  • [ 5422-50-4 ]
  • [ 153624-38-5 ]
  • [ 117712-97-7 ]
  • 4'-isobutyl-2-[(2-methylphenoxy)methyl]-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: 1-bromo-(2-methylphenoxymethyl)benzene; 4-isobutyl-phenylboronic acid With [resin-CH2N(CH3)3]2CO3 In water; N,N-dimethyl-formamide at 80℃; for 16h; Stage #2: With maleimido-CH2-PS resin In water; N,N-dimethyl-formamide at 90℃; for 10h;
  • 12
  • [ 99-90-1 ]
  • [ 153624-38-5 ]
  • [ 117712-97-7 ]
  • 1-(4'-isobutyl-1,1'-biphenyl-4-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: para-bromoacetophenone; 4-isobutyl-phenylboronic acid With [resin-CH2N(CH3)3]2CO3 In water; N,N-dimethyl-formamide at 80℃; for 16h; Stage #2: With maleimido-CH2-PS resin In water; N,N-dimethyl-formamide at 90℃; for 10h;
  • 13
  • [ 586-78-7 ]
  • [ 153624-38-5 ]
  • [ 117712-97-7 ]
  • 4-isobutyl-4'-nitro-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: para-nitrophenyl bromide; 4-isobutyl-phenylboronic acid With [resin-CH2N(CH3)3]2CO3 In water; N,N-dimethyl-formamide at 80℃; for 16h; Stage #2: With maleimido-CH2-PS resin In water; N,N-dimethyl-formamide at 90℃; for 10h;
  • 14
  • [ 104-92-7 ]
  • [ 153624-38-5 ]
  • [ 10468-83-4 ]
  • [ 117712-97-7 ]
  • 4'-isobutyl-1,1'-biphenyl-4-yl methyl ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 1-bromo-4-methoxy-benzene; 4-isobutyl-phenylboronic acid; Pd((PAnPh2)2Cl2 With [resin-CH2N(CH3)3]2CO3 In water; N,N-dimethyl-formamide at 80℃; for 16h; Stage #2: With [resin-CH2N(CH3)3]2CO3; 4-[(9-anthrylmethyl)amino]carbonyl}phenylboronic acid In water; N,N-dimethyl-formamide at 80℃; Stage #3: With maleimido-CH2-PS resin In water; N,N-dimethyl-formamide at 90℃; for 10h;
  • 15
  • [ 153624-38-5 ]
  • [ 849216-79-1 ]
  • 4'-isobutyl-biphenyl-4-sulfonic acid [2-(1H-indol-3-yl)-ethyl]-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene
  • 16
  • [ 10182-48-6 ]
  • [ 153624-38-5 ]
  • C75H80B5N5O10 [ No CAS ]
  • 17
  • [ 1011531-42-2 ]
  • [ 153624-38-5 ]
  • C32H35NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With cesium fluoride In 1,2-dimethoxyethane at 100℃; for 5h; 17 (S)-3-(4-(3-(4-Isobutyl)-phenyl-4-methylbenzyloxy)phenyl)-3-(isoxazol-3-yl)propanoic acid (17).; A solution of (S)-ethyl 3-(4-(3-iodo-4- methylbenzyloxy)phenyl)-3-(isoxazol-3-yl)propanoate 17.1 (35 mg, 0.072 mmol), terakis(triphenylphosphine)palladium (32 mg, 0.028 mmol), CsF (85 mg, 0.56 mmol), and 4-isobutylphenylboronic acid (50 mg, 0.28 mmol) in DME (1 mL), was stirred at 100 °C for 5 hours and then loaded on a silica gel cartridge and chromatographed (silica gel, 1 :4 EtOAc/hexane) to afford the corresponding ester. The ester was dissolved in EtOH (1 mL) and LiOH in water (1 mL, 1 N solution) was added. The mixture was stirred at 23 0C for 2 hours. The mixture was then filtered and purified by reverse phase HPLC to give compound 17 (1.62 mg) after lyophilization. MS ESI (pos.) m/e 470.2 (M+H). 1H NMR (500 MHz, CD3OD) δ ppm 8.52 (1 H, s), 7.20 - 7.32 (8 H, m), 6.95 - 6.99 (2 H, m), 6.30 (1 H, s), 5.07 (2 H, s), 4.59 - 4.56 (1 H, m), 3.21 - 3.17 (1 H, m), 2.97 - 2.92 (1 H, m), 2.55 (2 H, d, J=7.3 Hz), 2.26 (3 H3 s), 1.96 - 1.90 (1 H, m), 0.97 (6 H, d, 7=6.6 Hz).
  • 18
  • [ 524-38-9 ]
  • [ 153624-38-5 ]
  • [ 889668-95-5 ]
YieldReaction ConditionsOperation in experiment
81% With copper diacetate In 1,1-dichloroethane at 20℃; for 5h; Molecular sieve; 49.49a Example 49; Compound of Formula VII, Wherein R1 and R2 Taken Together with the Carbon Atom to which they are Attached are CNO[4-isobutyl-phenyl], R20H, and Rx=Ac; Step 49a.; A mixture of commercially available hydroxyl phthalimide (1 mmol), 4-isobutyl-phenyl boronic acid (2 eq.), copper acetate (1 eq.) and 4 molecular sieves (265 mg) in dichloroethane (5 ml) was stirred at room temperature for 5 hours. The green suspension was evaporated to dryness and the residue was purified by column chromatography eluting with hexane/CH2Cl2 (1:1) to yield a light yellow solid (81%). MS (ESI): m/z 295.98 [M+H]. 13C NMR(CDCl3, ppm) δ: 163.3, 157.3, 138.4, 135.1, 130.4, 129.1, 124.2, 114.8, 44.8, 30.5, 22.5.
  • 19
  • 4-nitrophenyl 2-iodobenzenesulphonate [ No CAS ]
  • [ 153624-38-5 ]
  • 4-nitrophenyl 4'-isobutyl-2-biphenylsulphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In ethanol; water; toluene 46.ii EXAMPLE 46 (ii) A mixture of 4-nitrophenyl 2-iodobenzenesulphonate (0.405 g), 4-isobutylphenylboronic acid (obtained as described in European Patent Application, publication No. 0569193) (0.179 g), tetrakis(triphenylphosphine)palladium(0) (0.058 g), toluene (15 ml), ethanol (10 ml) and 2M sodium carbonate solution (5.5 ml) was stirred vigorously and heated under reflux for 5 hours. Water (20 ml) was added and the mixture was extracted with ethyl acetate (2*25 ml). The combined extracts were washed with saturated sodium chloride solution (25 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by elution with ethyl acetate/hexane (1:3 v/v) through a silica gel Mega Bond Elut column to give 4-nitrophenyl 4'-isobutyl-2-biphenylsulphonate (0.349 g); 1 H NMR (d6 -DMSO): 0.9 (d,6H), 1.8-2.0 (m,1H), 2.5 (d,2H), 7.1-7.25 (m,4H), 7.35 (d,2H), 7.55 (d,1H), 7.7 (t,1H), 7.9 (t,1H), 8.05 (d,1H), 8.2 (d,2H); mass spectrum (+ve FAB, DMSO/methanol/NBA): 412 (H+H)+.
  • 20
  • [ 186497-45-0 ]
  • [ 153624-38-5 ]
  • N-(isobutoxycarbonyl)-2-(4-isobutylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In ethanol; water; toluene 1.iii EXAMPLE 1 (iii) A solution of 2-chloro-N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (4.0 g), 4-isobutylphenylboronic acid (obtained as described in European Patent Application, publication No. 0569193) (1.72 g) and tetrakis(triphenylphosphine)palladium(0) (0.334 g) in toluene (80 ml) and ethanol (40 ml) was deoxygenated by evacuation and refilling with argon (4 cycles). 2M Sodium carbonate solution (25 ml) was then added. The mixture was stirred and heated under reflux for 16 hours. Water (100 ml) was added and the mixture was extracted with ethyl acetate (4*40 ml). The organic extracts were washed with water (50 ml) and saturated sodium chloride solution (50 ml) then dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with 0-20% ethyl acetate/hexane through a 20 g silica gel Mega Bond Elut column to give N-(isobutoxycarbonyl)-2-(4-isobutylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (3.1 g) as a solid, m.p. 133°-137° C.; 1 H NMR (CDCl3): 0.7 (d, 6 H), 0.9 (d, 6 H), 1.7 (m, 1 H), 1.9 (m, 1 H), 2.5 (m, 5 H), 3.9 (d, 2 H), 4.0 (s, 3 H), 7.2 (d, 2 H), 7.5 (m, 3 H), 8.85 (dd, 1 H), 8.9 (s, 1 H), 9.0 (dd, 1 H); mass spectrum (+ve ESP): 513 (M+H)+.
  • 21
  • 4-nitrophenyl 2-chloropyridine-3-sulphonate [ No CAS ]
  • [ 153624-38-5 ]
  • 4-nitrophenyl 2-(4-isobutylphenyl)pyridine-3-sulphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride In water; toluene 5.ii EXAMPLE 5 (ii) Tetrakis(triphenylphosphine)palladium(0) (0.076 g) was added to a deoxygenated mixture of 4-nitrophenyl 2-chloropyridine-3-sulphonate (0.69 g), 4-isobutylphenylboronic acid (0.47 g), potassium fluoride (0.38 g), toluene (15 ml) and water (2.5 ml) and the mixture was stirred and heated under reflux for 24 hours. Water (50 ml) was added and the mixture was extracted with ethyl acetate (2*80 ml). The organic extracts were washed with saturated sodium chloride solution and then combined and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with dichloromethane/hexane (1:1-1:0 v/v) then dichloromethane/hexane/ethyl acetate (10:9:1 v/v) through a silica gel Mega Bond Elut column followed by recrystallisation from ethyl acetate/hexane to give 4-nitrophenyl 2-(4-isobutylphenyl)pyridine-3-sulphonate (0.50 g), m.p. 123°-124° C.; 1 H NMR (d6 -DMSO): 0.9 (d, 6 H), 1.9 (m, 1 H), 2.55 (d, 2 H), 7.2-7.3 (m, 4 H), 7.5 (d, 2 H), 7.7 (dd, 1 H), 8.2 (d, 2 H), 8.4 (dd, 1 H), 9.0 (dd, 1 H); mass spectrum (+ve FAB, NBA/DMSO): 413 (M+H)+.
  • 22
  • [ 121-43-7 ]
  • [ 57181-82-5 ]
  • [ 153624-38-5 ]
YieldReaction ConditionsOperation in experiment
2.3 g (46%) With hydrogenchloride; iodine; magnesium In tetrahydrofuran 21.A A. A. 4-isobutyl-phenylboronic acid To a suspension of 0.68 g (28.15 mmol) of magnesium turnings in 50 mL of tetrahydrofuran under argon, a crystal of iodine was added and a solution of 4-bromo-isobutylbenzene (6.0 g, 28.15 mmol) in 25 mL of tetrahydrofuran was added at such a rate that a gentle reflux was maintained. The mixture was refluxed for an additional 1 hour, cooled to room temperature and added in portions over 15 min to a solution of trimethylborate (2.93 g, 28.15 mmol) in 50 mL of ether at -78° C. under argon. After 30 min at -78° C., the solution was warmed to room temperature, stirred for 90 minutes and 10% aqueous hydrochloric acid (100 mL) was added. After 10 minutes, the solution was extracted with ether (3*100 mL) and the combined ether extracts were extracted with 1M sodium hydroxide (3*100 mL). The aqueous extracts were acidified with dilute hydrochloric acid to pH 2 and extracted with ether (3*100 mL). The combined ether extracts were washed once with water (100 mL), dried and evaporated to afford 3.5 g of a white solid. Crystallization from ether/hexanes provided 2.3 g (46%) of compound A as a white solid in two crops, m.p. 134°-135° C.
  • 23
  • [ 153624-38-5 ]
  • 4-isobutyl-2-nitro-phenylboronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; nitric acid In acetic anhydride; ethyl acetate 32.A A. A. 4-isobutyl-2-nitro-phenylboronic acid To a suspension of 4-isobutyl-phenylboronic acid (0.9 g, 5.05 mmol) in acetic anhydride (9 mL) at -10° C., fuming nitric acid (0.4 mL) was added over 10 minutes. The mixture was stirred for 1 hour, warmed to room temperature and stirred for an additional 1.5 hours. The clear orange solution was added to 100 mL of ice, stirred for 3 hours and azeotroped with water (4*100 mL). The residue was partitioned between 25 mL each of ether and water and the ether layer was dried and evaporated to provide 0.75 g of yellow solid. The solid was dissolved in ethyl acetate (25 mL) and the solution was extracted with 1N aqueous sodium hydroxide (2*25 mL). The combined aqueous extracts were acidified to pH 2 using 2N aqueous hydrochloric acid and extracted with ethyl acetate (2*25 mL). The combined organic extracts were washed once with water, dried and evaporated to provide 0.63 g of light yellow solid. Reverse phase preparative HPLC on a 30*500 mm ODS S10 column using 76% solvent A (90% MeOH, 10% H2 O, 0.1% TFA) and 24% solvent B (10% MeOH, 90% H2 O, 0.1% TFA) provided 0.16 g of compound A as light yellow solid.
  • 24
  • [ 1208223-18-0 ]
  • [ 153624-38-5 ]
  • [ 1208223-19-1 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 4-[1-(6-chloro-pyridin-3-yloxy)-butyl]-benzoic acid methyl ester; 4-isobutyl-phenylboronic acid In water; toluene Reflux; Stage #2: With potassium fluoride In water; toluene at 20 - 90℃; 1-F.C 4-[l-(6-Chloro-pyridin-3-yloxy)-butyl]-benzoic acid methyl ester (300 mg, 0.94 mmol) in toluene (3 mL) was treated with water (3 mL), tetrakis (triphenylphosphine) palladium (108 mg, 0.1 mol%), and 4-isobutylphenylboronic acid (334 mg, 1.87 mmol). This solution was heated to reflux for S min, at which point it was allowed to cool to room temperature. Potassium fluoride (109 mg, 1.87 mmol) was added in one portion, and the reaction was then heated at 90 °C for 16 hrs. The reaction was evaporated to dryness by rotary evaporator and purified by column chromatography on silica gel (100 x 42 mm S1O2) eluting with 10% acetone in hexanes to yield 4-{l-[6-(4-isobutyl-phenyl)-pyridin- 3-yloxy]-butyl} -benzoic acid methyl ester as a light yellow oil (353 mg, 90%). 1H NMR (300 MHz, CDCl3): 58.33 (d, J = 2.9 Hz, 1 H), 8.03 (d, J = 8.0 Hz, 2 H), 7.79 (d, J = 8.0 Hz, 2 H), 7.55 (d, J= 8.5 Hz, 1 H), 7.46 (d, J= 8.2 Hz, 2 H), 7.05-7.17 (m, 3 H), 5.13 (dd, J1 = 6.0 Hz, J2 = 1.8 Hz, 1 H), 3.94 (s, 3 H), 2.51 (d, J = 7.0 Hz, 2 H), 1.88-2.20 (m, 4 H), 1.40- 1.63 (m, 2 H), 0.96 (t, J = 7.3 Hz, 3 H), 0.92 (d, J = 6.7 Hz, 6 H). LC-MS m/z = 418 [C27H3INO3 + H]+
  • 25
  • [ 959150-64-2 ]
  • [ 153624-38-5 ]
  • [ 1216805-39-8 ]
  • 26
  • [ 26166-92-7 ]
  • [ 153624-38-5 ]
  • [ 1216805-28-5 ]
YieldReaction ConditionsOperation in experiment
90% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Methyldicyclohexylamine; sodium hydroxide In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; chemoselective reaction;
  • 27
  • [ 153624-38-5 ]
  • [ 350236-32-7 ]
  • methyl 5-chloro-4'-isobutyl-4-methoxybiphenyl-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In N,N-dimethyl-formamide at 70℃; Inert atmosphere;
  • 28
  • C11H4BrClF3O3Pol [ No CAS ]
  • [ 153624-38-5 ]
  • C21H17ClF3O3Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 70℃; solid phase reaction;
  • 29
  • [ 57311-18-9 ]
  • [ 153624-38-5 ]
  • [ 1414972-03-4 ]
YieldReaction ConditionsOperation in experiment
79% With potassium phosphate In water; toluene for 21h; Reflux; 1 Step 1 Synthesis of 4-(4-isobutylphenyl)-2-phenylpyridine A 250 mL round-bottomed flask was charged with 4-chloro-2-phenylpyridine (5 g, 26.4 mmol), (4-isobutylphenyl)boronic acid (7.04 g, 39.5 mmol), Pd2(dba)3(0.483 g, 0.527 mmol), dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-3-yl)phosphine (S-Phos) (0.866 g, 2.109 mmol), K3PO4(16.79 g, 79 mmol), toluene (100 mL) and water (10 mL) to give a yellow suspension. The suspension was heated to reflux for 21 hrs. The reaction mixture was poured into water and extracted with EtOAc. The organic layers were combined and subjected to column chromatography (SiO2, 10% EtOAc in hexane) to yield 4-(4-isobutylphenyl)-2-phenylpyridine (6 g, 20.9 mmol, 79% yield).
  • 30
  • [ 1611001-74-1 ]
  • [ 153624-38-5 ]
  • [ 1611001-75-2 ]
YieldReaction ConditionsOperation in experiment
20.98% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere; 190 Example 190: 3-(4-lsobutylphenyl)-6-(6-methylpyridin-3-yl)-8-(trifluoro methyl)imidazo[1 ,2-a] pyridine The compound of example 1 81 (0.200 g, 0.562 mmol) was treated with 4- isobutylphenylboronic acid (0.1 20 mg, 0.674 mmol) in the presence of [1 , 1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.022 g, 0.028 mmol) and sodium carbonate (0.1 16 g, 0.842 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.50 g (20.98 %); 1 H NMR (DMSO-de, 300 MHz): δ 0.87 (d, 3H, J =6.3 Hz, CH3), 0.89 (d, 3H, J =6.3 Hz, CH3), 1 .76-1 .86 (m, 1 H, CH), 2.40 (d, 2H, J =7.2 Hz, CH2), 2.53 (s, 3H, CH3), 7.07 (d, 1 H, J =7.8 Hz, Ar), 7.34 (dd, 2H, J =2.4 Hz, J =8.1 Hz, Ar), 7.65 (dd, 3H, J =1 .8 Hz, J =8.1 Hz, Ar), 7.86 (s, 1 H, Ar), 8.00 (s, 1 H, Ar), 8.04 (dd, 1 H, J =2.4 Hz, J =8.1 Hz, Ar), 8.79 (s, 1 H, Ar); MS (ES+): m/e 410.2 (M+1 ).
  • 31
  • [ 1611001-92-3 ]
  • [ 153624-38-5 ]
  • [ 1611001-93-4 ]
YieldReaction ConditionsOperation in experiment
65.5% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere; 212 Example 212: 3-(4-lsobutylphenyl)-6-(2-methoxypyridin-3-yl)-8-(trifluoromethyl)imidazo [1,2-a] pyridine The compound of example 211 (0.200 g, 0.537 mmol) was treated with (4- isobutylphenyl)boronic acid (0.115 g, 0.645 mmol) in the presence of [1,1'- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.021 g, 0.027 mmol) and sodium carbonate (0.111 mg, 0.806 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.152 g (65.5 %); 1H NMR (DMSO-de, 300 MHz): δ 0.91 (d, 6H, J =3.0 Hz, 2CH3), 1.88-1.92 (m, 1H, CH), 2.50- 2.53 (m, 2H, CH2), 3.92 (s, 1H, OCH3), 7.13 (dd, 1H, J =3.0 Hz, J =4.2 Hz, Ar), 7.37 (d, 2H, J =6.0 Hz, Ar), 7.65 (d, 2H, J =6.0 Hz, Ar), 7.89 (s, 1H, Ar), 7.95 (s, 1H, Ar), 8.02 (d, 1H, J =4.2 Hz, Ar), 8.24 (d, 1H, J =2.7 Hz, Ar), 8.87 (s, 1H, Ar); MS (ES+): m/e 426.2 (M+1).
  • 32
  • [ 1611002-27-7 ]
  • [ 153624-38-5 ]
  • [ 1611002-03-9 ]
YieldReaction ConditionsOperation in experiment
30.3% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere; 226 Example 226: 5-(3-(4-lsobutylphenyl)-8-(trifluoromethyl)imidazo[1 ,2-a] pyridin-6-yl) picolinonitrile The compound of example 225 (0.200 g, 0.545 mmol) was treated with (4- isobutylphenyl)boronic acid (0.1 16 g, 0.654 mmol) in the presence of [1 ,1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(ll) complex with dichloromethane (0.022 g, 0.027 mmol) and sodium carbonate (0.113 g, 0.817 mmol) in dry dimethylformamide (10 mL) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.70 g (30.3 %); 1H NMR (DMSO-de, 300 MHz): δ 0.93 (d, 6H, J =3.0 Hz, 2CH3), 1.86-1.97 (m, 1H, CH), 2.50- 2.56 (m, 2H, CH2), 7.38 (d, 2H, J =9.0 Hz, Ar), 7.72 (d, 2H, J =9.0 Hz, Ar), 7.94 (s, 1H, Ar), 8.18 (d, 2H, J =9.0 Hz, Ar), 8.52 (dd, 1H, J =3.0 Hz, J=8.1 Hz, Ar), 9.06 (s, 1H, Ar), 9.22 (d, 1 H, J =3.0 Hz, Ar); MS (ES+): m/e 421.4 (M+1 ).
  • 33
  • [ 1611001-01-4 ]
  • [ 153624-38-5 ]
  • [ 1611001-02-5 ]
YieldReaction ConditionsOperation in experiment
29% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere; 29 Example 29: 3-(4-lsobutylphenyl)-6-(6-methoxypyridin-3-yl) imidazo [1 , 2-a] pyridine-8- carboxylic acid The compound of example 28 (0.300 g, 0.862 mmol) was treated with (4- isobutylphenyl)boronic acid (0.1 84 g, 1 .03 mmol) in the presence of [1 , 1 '- bis(diphenylphosphino)-ferrocene]dichloropalladium(l l) complex with dichloromethane (0.021 g, 0.026 mmol) and sodium carbonate (0.274 g, 2.59 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 0.1 g (29 %) ; 1 H NMR (DMSO-d6, 300 MHz): δ 0.92 (d, 6H, J=6.0 Hz, 2CH3), 1 .90-1 .93 (m, 1 H, CH), 2.53-2.55 (d, 2H, J=7.2 Hz, CH2), 3.91 (s, 3H, OCH3), 6.97 (d, 1 H, J=9.0 Hz, Ar), 7.05 (t, 1 H, J=6.0 Hz, Ar), 7.73-7.37 (m, 2H, Ar), 7.54-7.60 (m, 3H, Ar); 7.78 (s, 1 H, Ar), 8.47-8.53 (m, 1 H, Ar), 8.94 (d, 1 H, J=2.1 Hz, Ar), MS (ES+): m/e 402 (M+1 ).
  • 34
  • [ 1611001-11-6 ]
  • [ 153624-38-5 ]
  • [ 1610999-85-3 ]
YieldReaction ConditionsOperation in experiment
70% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere; 62 Example 62: 3-(4-lsobutylphenyl)-8-methyl-6-(6-methylpyridin-3-yl)imidazo[1,2-a] pyridine The compound of example 45 was treated with (4-isobutylphenyl)boronic acid (0.118 g, 0.662 mmol) in the presence of [1 ,1 '-bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.016 g, 0.020 mmol) and sodium carbonate (0.140 g, 1.32 mmol) in dry dimethylformamide according to the procedure for the preparation of the compound of example 2 to afford the title compound . Yield: 0.165 g (70 %); 1H NMR (DMSO-d6, 300 MHz): δ 0.91 (d, 6H, J=6.6 Hz, 2CH3), 1.85-1.94 (m, 1H, CH), 2.53 (s, 3H, CH3), 2.60 (s, 3H, CH3), 2.89 (s, 2H, CH2), 7.34 (m, 3H, 3Ar), 7.48 (s, 1H, Ar), 7.64-7.66 (m, 2H, Ar), 7.74 (s, 1H, Ar), 8.01 (dd, 1H, J=8.1, 2.1 Hz, Ar), 8.52 (s, 1H, Ar), 8.78 (d, 1H, J=2.1 Hz, Ar); MS (ES+): m/e 356 (M+1).
  • 35
  • tert-butyl [(2S,3S)-1-{4-bromophenyl-[2-(pyridin-2-yl)cyclopropanecarbonyl]amino}-3-methylpentan-2-yl]carbamate [ No CAS ]
  • [ 153624-38-5 ]
  • tert-butyl [(2S,3S)-1-{(4′-isobutylbiphenyl-4-yl)[2-(pyridin-2-yl)cyclopropanecarbonyl]amino}-3-methylpentan-2-yl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,2-dimethoxyethane; water at 160℃; for 0.1h; Sealed tube; Microwave irradiation;
  • 36
  • [ 3638-04-8 ]
  • [ 153624-38-5 ]
  • 2-chloro-4-(4-isobutylphenyl)-6-methoxy-1,3,5-triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene; at 70℃; for 3.5h;Inert atmosphere; Under an argon atmosphere, a suspension of 4-(2-methylpropyl)phenylboronic acid (35 g, 200 mmol), <strong>[3638-04-8]2,4-dichloro-6-methoxy-1,3,5-triazine</strong> (46 g, 260 mmol), tetrakis(triphenylphosphine)palladium(0) (2.3 g, 2.0 mmol) and sodium carbonate (63 g, 590 mmol) in toluene (280 ml) and distilled water (280 ml) was stirred at 70 C. for 3.5 hr. At room temperature, to the reaction mixture were added water, ethyl acetate, and n-hexane, and the mixture was partitioned. The organic layer was washed with saturated brine, dried over sodium sulfate, filtered to remove sodium sulfate, and concentrated under reduced pressure to give the title compound (60 g) as a crude product.
  • 37
  • [ 153624-38-5 ]
  • {4-chloro-3-[4-(4-isobutylphenyl)-6-methoxy-1,3,5-triazin-2-yl]phenyl}methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / 3.5 h / 70 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; cesium fluoride / water; acetonitrile / 2 h / 67 °C / Inert atmosphere
  • 38
  • [ 153624-38-5 ]
  • tert-butyl N-{4-chloro-3-[4-(4-isobutylphenyl)-6-methoxy-1,3,5-triazin-2-yl]benzyl}-N-(tert-butoxycarbonyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / 3.5 h / 70 °C / Inert atmosphere 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; cesium fluoride / water; acetonitrile / 2 h / 67 °C / Inert atmosphere 3.1: triphenylphosphine; carbon tetrabromide / chloroform / 0.17 h / 20 °C / Inert atmosphere 3.2: 0.25 h / 20 °C
  • 39
  • [ 153624-38-5 ]
  • (Ra)-3,3’-diiodo-2,2’-bis(methoxymethoxy)-1,1’-binaphthalene [ No CAS ]
  • C40H38O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-isobutyl-phenylboronic acid; (Ra)-3,3’-diiodo-2,2’-bis(methoxymethoxy)-1,1’-binaphthalene With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; water at 90℃; Inert atmosphere; Stage #2: With hydrogenchloride In 1,4-dioxane; water at 70℃; for 2h;
  • 40
  • [ 33035-41-5 ]
  • [ 657-84-1 ]
  • [ 153624-38-5 ]
  • 4-isobutylphenyl(mesityl)iodonium tosylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: 4-isobutyl-phenylboronic acid With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2-(diacetoxyiodo)mesitylene In dichloromethane at 0 - 20℃; Inert atmosphere; Stage #3: sodium tosylate In dichloromethane; water for 0.5h; Inert atmosphere;
  • 41
  • [ 153624-38-5 ]
  • 6-isobutyl-1,4-dihydro-1,4-epoxynaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 1.3: 0.5 h / Inert atmosphere 2.1: lithium hexamethyldisilazane / toluene / 3 h / 13 °C / Sealed tube; Inert atmosphere
  • 42
  • 7-chloro-2-(3',5'-dimethylphenyl)quinoline [ No CAS ]
  • [ 153624-38-5 ]
  • 2-(3,5-dimethylphenyl)-7-(4-isobutylphenyl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In water; toluene Inert atmosphere; Reflux; 81 Synthesis of 2- (3,5-dimethylphenyl) -7- (4-isobutyl-phenyl) quinoline. 7-chloro-2- (3,5-dimethylphenyl) quinoline (3.5 g, 13.1mmol), (4-isobutyl-phenyl) boronic acid (3.49 g, 19.6 mmol), Pd2dba3 (0.24 g, 0.26 mmol), di cyclohexyl (2 ', 6'-dimethoxy- [1,1' -biphenyl] -2-yl) phosphine (SPhos) (0.43 g, 1.05 mmol), and K3PO4 (5.55 g, 26.1 mmol), a toluene (110 mL) and was diluted with water (20 mL). The reaction mixture was degassed for 15 minutes by bubbling nitrogen. After the reaction mixture was heated to reflux overnight. Upon completion, the mixture was cooled and extracted with EA and washed with water. Use the crude product with heptane / EA (95/5) solvent system was purified by column chromatography. By grinding the combined product from heptane to give the pure 2- (3,5-dimethylphenyl) -7- (4-isobutyl-phenyl) quinoline (3.10 g, 65% yield) as a white powder.
  • 43
  • [ 1030604-42-2 ]
  • [ 153624-38-5 ]
  • 3-(4-isobutylphenyl)-2H-furo[2,3-c]pyran-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In toluene for 24h; Inert atmosphere; Schlenk technique; Reflux;
  • 44
  • (S)-ethyl 2-(5-bromo-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate [ No CAS ]
  • [ 153624-38-5 ]
  • (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-isobutylphenyl)-2,6-dimethylpyridin-3-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
59.1% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 90℃; for 9h; Inert atmosphere; (S)-Ethyl 2-(tert-butoxy)-2-(4-(4, 4-dimethylpiperidin-l-yl)-5-(4-isobutylphenyl)-2, 6- dimethylpyridin-3-yl)acetate (S)-Ethyl 2-(tert-butoxy)-2-(4-(4, 4-dimethylpiperidin-l-yl)-5-(4-isobutylphenyl)-2, 6- dimethylpyridin-3-yl)acetate: A mixture of (S)-ethyl 2-(5-bromo-4-(4,4- dimethylpiperidin-l-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate (0.02 g, 0.044 mmol), (4-isobutylphenyl)boronic acid (0.016 g, 0.088 mmol) and 2M Na2C03 (0.055 ml, 0.110 mmol) in DMF (1 mL) was degassed for 3 min. Then, Pd(Ph3P)4 (5.07 mg, 4.39 μπιο) was degassed for 1 min and placed in a pre-heated oil bath at 90 °C. After 9 h, cooled and purified by prep-HPLC to afford (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4- dimethylpiperidin-l-yl)-5-(4-isobutylphenyl)-2,6-dimethylpyridin-3-yl)acetate (0.0132 g, 0.026 mmol, 59.1 % yield) as brown paste. LCMS (M+H) = 509.4.
  • 45
  • [ 126-30-7 ]
  • [ 153624-38-5 ]
  • C15H23BO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% In diethyl ether Inert atmosphere;
  • 46
  • [ 153624-38-5 ]
  • 3,12-diisobutyldibenzo[h,rst]pentaphene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: diethyl ether / Inert atmosphere 2: carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) / toluene / 10 h / 120 °C / Inert atmosphere; Schlenk technique 3: sodium hydride / dimethyl sulfoxide; tetrahydrofuran / 1 h / 50 °C / Inert atmosphere; Darkness 4: indium(III) chloride / 1,2-dichloro-ethane / 12 h / Inert atmosphere; Schlenk technique; Reflux
  • 47
  • [ 153624-38-5 ]
  • C36H36O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / Inert atmosphere 2: carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) / toluene / 10 h / 120 °C / Inert atmosphere; Schlenk technique 3: sodium hydride / dimethyl sulfoxide; tetrahydrofuran / 1 h / 50 °C / Inert atmosphere; Darkness
  • 48
  • [ 153624-38-5 ]
  • 1,4-bis(4-isobutylphenyl)-9,10-anthracenedione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diethyl ether / Inert atmosphere 2: carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) / toluene / 10 h / 120 °C / Inert atmosphere; Schlenk technique
  • 49
  • [ 23170-45-8 ]
  • [ 153624-38-5 ]
  • methyl 1-(4-isobutylphenyl)-3-methyl-1H-pyrazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With pyridine; copper diacetate; In N,N-dimethyl-formamide; at 25℃; for 14h; A mixture of methyl 3-methyl- 1H-pyrazole-4-carboxylate (250.0 mg, 1.78 mmol), 4- isobutylphenyl boronic acid (412.9 mg, 2.32 mmol), pyridine (282.2 mg, 3.57 mmol) andcopper(II) acetate (486.0 mg, 2.68 mmol) in N,N-dimethylformamide (6 mL) was stirred at 25C for 14 h. The reaction was diluted with EtOAc (120 mL), washed with brine (50 mL x 3), dried over Na2SO4 and concentrated. The residue was purified by prep-TLC (20% EtOAc in petroleum ether, Rf = 0.45) to give methyl 1-(4-isobutylphenyl)-3-methyl-1H-pyrazole-4- carboxylate (350 mg, 72% yield) as a white solid. LCMS (Method 5-95 AB, ESI): tR = 0.996mi [M+Hj = 272.9.
  • 50
  • [ 22927-61-3 ]
  • [ 153624-38-5 ]
  • 1-methoxymethyl-2-(4-iso-butylphenyl)-4,5-dibromoimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; water; toluene for 18h; Inert atmosphere; Reflux; 1 1-Methoxymethyl-2-(4-iso-butylphenyl)-4,5-dibromoimidazole (6). Compound 5 (3.66 g, 10.2 mmol) and 4-iso-butylphenylboronic acid (1.89 g, 10.6 mmol) were dissolved in toluene/MeOH (5:1, 105.0 mL), and an aqueous solution of K2CO3 (2.0 M, 11.5 mL) was added. The mixture was degassed with argon for 20 minutes while stirring, followed by the addition of Pd(PPh3)4 (1.23 g, 1.1 mmol). The mixture was stirred at reflux for 18 h. It was cooled to room temperature and diluted with water (40 mL) and EtOAc (20 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layer was washed with brine (20 mL) and dried (Na2SO4). The solvent was removed in vacuo, and the crude product was purified by flash chromatography (silica, 100% hexanes to 9:1 hexanes/EtOAc) to give a pale-yellow viscous oil (3.83 g, 86%). 1H NMR (600 MHz, CDCl3) δ0.91 (d, 6H, J=6.8 Hz, CH2CH(CH3)2)), 1.89 (nonet, 1H, J=6.8 Hz, CH2CH(CH3)2), 2.52 (d, 2H, J=6.8 Hz, CH2CH(CH3)2), 3.44 (s, 3H, OCH3), 5.27 (s, 2H, NCH2O), 7.23 (d, 2H, J=8.2 Hz, ArH), 7.65 (d, 2H, J=8.2 Hz, ArH); 13C NMR (150 MHz, CDCl3) δ22.5, 30.4, 45.4, 56.8, 76.4, 105.1, 118.0, 126.8, 128.8, 129.7, 144.1, 150; HRMS (ESI): calcd for C15H19Br2N2O 400.9859, found 400.9895 [MH]+.
  • 51
  • [ 153624-38-5 ]
  • 1-methoxymethyl-2-(4-iso-butylphenyl)-5-tributylstannyl-4-bromoimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; methanol; water / 18 h / Inert atmosphere; Reflux 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C 2.2: 0.5 h / -78 °C
  • 52
  • [ 153624-38-5 ]
  • 1-methoxymethyl-2-(4-iso-butylphenyl)-4-bromo-5-(4-pyridyl)imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; methanol; water / 18 h / Inert atmosphere; Reflux 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C 2.2: 0.5 h / -78 °C 3.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 45 h / 110 °C / Inert atmosphere
  • 53
  • [ 153624-38-5 ]
  • 1-methoxymethyl-2-(4-iso-butylphenyl)-4-bromo-5-(4-fluorophenyl)imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; methanol; water / 18 h / Inert atmosphere; Reflux 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C 2.2: 0.5 h / -78 °C 3.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane; copper(l) iodide / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
  • 54
  • 2,3-dibromo-6-(2-methoxyethyl)-5,6-dihydro-7H-imidazo[1,5-a]imidazole-7-one [ No CAS ]
  • [ 153624-38-5 ]
  • 2-bromo-6-(2-methoxyethyl)-3-[4-(2-methylpropyl)phenyl]-5,6-dihydro-7H-imidazo[1,5-a]imidazol-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 6h; 9 Production Example 9 2-bromo-6-(2-methoxyethyl)-3-[4-(2-methylpropyl)phenyl]-5,6-dihydro-7H-imidazo[1,5-a]imidazol-7-one 2,3-dibromo-6- (2-methoxyethyl) -5,6-dihydro-7H-imidazo [1,5- a] imidazol-7-one (98 mg) obtained in Production Example 6, 4- Isobutylphenyl boronic acid (62 mg), tetrakis (triphenylphosphine) palladium (0) (34 mg), ethanol (1.0 mL), toluene (1.0 mL) and 2 M sodium carbonate aqueous solution (0.44 mL) Was stirred at 100 ° C. (oil bath temperature) for 6 hours. Water was added to the reaction solution, and the mixture was extracted three times with chloroform. The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by reverse phase column chromatography (SunFire (registered trademark), 0.1% trifluoroacetic acid / water: 0.1% trifluoroacetic acid / acetonitrile = 90: 10 to 0: 100) to give the title compound (82 mg) as amorphous.
  • 55
  • 2,3-dibromo-6-(2-methoxyethyl)-5,6-dihydro-7H-imidazo[1,5-a]imidazole-7-one [ No CAS ]
  • [ 153624-38-5 ]
  • 6-(2-methoxyethyl)-2-methyl-3-[4-(2-methylpropyl)phenyl]-5,6-dihydro-7H-imidazo[1,5-a]imidazol-7-one [ No CAS ]
  • 6-(2-methoxyethyl)-3-[4-(2-methylpropyl)phenyl]-5,6-dihydro-7H-imidazo[1,5-a]imidazol-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; toluene; water / 6 h / 100 °C 2: sodium carbonate; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride / ethanol; toluene; water / 1 h / 100 °C
  • 56
  • 3-bromo-1-methyl-N-(methylsulfonyl)-1H-indole-6-carboxamide [ No CAS ]
  • [ 153624-38-5 ]
  • 3-(4-isobutylphenyl)-1-methyl-N-(methylsulfonyl)-1H-indole-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane at 100℃; for 2h; Inert atmosphere;
  • 57
  • (S)-N-(3-amino-1-cyano-3-oxopropyl)-3-((4-bromophenyl)sulfonyl)-2,2-dimethylpropanamide [ No CAS ]
  • [ 153624-38-5 ]
  • (S)-N-(3-amino-1-cyano-3-oxopropyl)-3-((4’-isobutyl-[1,1’-biphenyl]-4-yl)sulphonyl)-2,2-dimethylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; General Procedure of Cross Coupling Reaction (15a-m and 16a-n); General procedure: To a solu of 14 (60 mg, 0.14 mmol) in DMF (2 mL) was added selected aryl boronic acid (0.22 mmol) and 2 M Na2CO3 (0.2 mL). The reaction mixture was degassed with bubbling N2 (g) for 10 mins. Added PdCl2(dppf) (10 mg, 0.013 mmol), heated to 60 C and stirred for 10-30 mins. The reaction was cooled to room temperature, diluted with 5% LiCl (aq. Solu., 16 mL) and extracted with EtOAc (2 x 10 mL). The combined organic extracts were washed with 5% LiCl (aq. Solu., 2 x 15 mL) and brine (20 mL), dried over Na2SO4, passed through a plug of celite and concentrated under vacuum. The residue was purified by column chromatography using 0 to 100% EtOAc in hexanes then 0 to 10% MeOH in EtOAc to afford the desired product:
  • 58
  • [ 76-09-5 ]
  • [ 153624-38-5 ]
  • [ 1033753-01-3 ]
YieldReaction ConditionsOperation in experiment
57% In tetrahydrofuran at 20℃; for 12h; Molecular sieve;
  • 59
  • N-(bis(2-methoxyphenyl)methyl)-2-bromopropanamide [ No CAS ]
  • [ 153624-38-5 ]
  • (R)-N-(bis(2-methoxyphenyl)methyl)-2-(4-isobutylphenyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With potassium fluoride; C46H59NO2P2; palladium diacetate In toluene at 60℃; for 48h; Schlenk technique; Inert atmosphere; enantioselective reaction;
  • 60
  • [ 153624-38-5 ]
  • 2,6-dichloro-4'-isobutyl-[1,1'-biphenyl]-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate / water / 1 h / Heating 2: ammonium formate; zinc / water; methanol / 2 h / Heating
  • 61
  • [ 153624-38-5 ]
  • N-(2,6-dichloro-4'-isobutyl-[1,1'-biphenyl]-4-yl)-2-(4-(ethylsulfonyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate / water / 1 h / Heating 2: ammonium formate; zinc / water; methanol / 2 h / Heating 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C
  • 62
  • [ 62778-19-2 ]
  • [ 153624-38-5 ]
  • 2,6-dichloro-4'-isobutyl-4-nitro-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
54.9% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate In water for 1h; Heating; 26.1 Step 1:
Synthesis of 2,6-dichloro-4'-isobutyl-4-nitro-1,1'-biphenyl
(4-Isobutylphenyl)boronic acid (300 mg, 1.68 mmol), 1,3-dichloro-2-iodo-5-nitrobenzene (636 mg, 2 mmol), potassium carbonate (680 mg, 5 mmol), PdCl2(dtbpf) (55 mg, 0.08 mmol) and 2 wt% Tween 20 in water (10 mL) were added in a 20 mL single-neck flask, and the mixture was heated to react at 80□ for 1 hour. After completion of the reaction, the mixture was extracted with ethyl acetate (3∗10 mL). The combined organic layers were concentrated in vacuo to remove the solvent, and the residue was separated by a silica gel column (elutent: petroleum ether) to give a product (colorless oil, 300 mg), with a yield of 54.9%.
  • 63
  • [ 153624-38-5 ]
  • [ 10342-60-6 ]
YieldReaction ConditionsOperation in experiment
84% With 1,1,1,3',3',3'-hexafluoro-propanol; 2-nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide at 60℃; for 19h; Inert atmosphere; Schlenk technique;
  • 64
  • [ 15973-65-6 ]
  • [ 153624-38-5 ]
  • 3-(4-isobutylphenyl)-1-(4-methoxyphenyl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With copper diacetate; palladium diacetate; 1,2-bis-(diphenylphosphino)ethane In water; dimethyl sulfoxide at 70℃; for 2h; chemoselective reaction;
  • 65
  • [ 1381869-21-1 ]
  • [ 153624-38-5 ]
  • 8-(4-isobutylphenyl)-2-phenylimidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With palladium diacetate; triphenylphosphine In ethanol; toluene Reflux;
  • 66
  • N-benzhydryl-2-bromo-2-(naphthalen-2-yl)acetamide [ No CAS ]
  • [ 153624-38-5 ]
  • N-benzhydryl-2-(4-isobutylphenyl)-2-(naphthalen-2-yl)acetamide [ No CAS ]
  • (S)-N-benzhydryl-2-(4-isobutylphenyl)-2-(naphthalen-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82 % ee With potassium fluoride; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; C34H47NO3P2 In toluene at 50℃; for 48h; Schlenk technique; Inert atmosphere; Overall yield = 75 percent; Overall yield = 90.6 mg; enantioselective reaction;
  • 67
  • (propane-2,2-diylbis(2-chloro-4,1-phenylene))dimethanol [ No CAS ]
  • [ 153624-38-5 ]
  • (propane-2,2-diylbis(4'-isobutyl-[1,1'-biphenyl]-5,2-diyl))dimethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium <i>tert</i>-butylate In 1,4-dioxane for 16h; Reflux; S25 (Propane-2,2-diylbis(4'-isobutyl-[1,1'-biphenyl]-5,2-diyl))dimethanol S20 (200 mg, 0.615 mmol) was taken up in dioxane (10 mL) with 4-isopropylphenylboronic acid (500 mg, 2.82 mmol, 4.6 eq.) and KOtBu (200 mg, 1.77 mmol, 3.0 eq.). The solution was sparged with Ar for 15 min, then PEPPSI (80 mg, 0.120 mmol, 0.2 eq.) was added and the reaction heated to reflux for 16 h. The reaction was then cooled to r.t., diluted with CH2Cl2(100 mL) and washed with 2 M NaOH(aq) (3 × 100 mL). The organic phase was dried over Na2SO4, filtered, and the solvent removed under reduced pressure. The residue was purifiedby flash column chromatography (PE:EtOAc 4:1) to furnish S25 (242 mg, 0.465 mmol, 76%) as a colourless oil.
  • 68
  • 5-chloro-3-iodofuro[3,2-b]pyridine [ No CAS ]
  • [ 153624-38-5 ]
  • 5-chloro-3-(4-isobutylphenyl)furo[3,2-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 60℃; Inert atmosphere; General procedure A for Suzuki cross-coupling of 5-chloro-3-iodofuro[3,2-b]pyridine (9) atposition C-3. General procedure: A round-bottom flask with 5-chloro-3-iodofuro[3,2-b]pyridine (0.5 mmol), K3PO4 (1.75 mmol),Pd(dppf)Cl2 (0.025 mmol) and boronic acid/ester or potassium trifluoroborate salt (0.55 mmol)was three times evacuated and backfilled with argon. Degassed (by freeze-thaw-pump cycle)mixture of 1,4-dioxane/H2O (4 mL + 1 mL) was added and the reaction mixture was stirred at60 °C; the progress of the reaction was followed by TLC and/or by 1H NMR.
  • 69
  • C12H15BrN2O [ No CAS ]
  • [ 153624-38-5 ]
  • C22H28N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 16h; Sealed tube; Inert atmosphere;
  • 70
  • 1-(2-methyl-6-(prop-1-en-2-yl)phenyl)-1H-pyrazole [ No CAS ]
  • [ 153624-38-5 ]
  • 1-(4'-isobutyl-3-methyl-[1,1'-biphenyl]-2-yl)-1H-pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate; silver(l) oxide In ethanol at 100℃; for 20h; Inert atmosphere; Schlenk technique;
  • 71
  • 2-((2Z,4E)-3-methyl-5-phenylpenta-2,4-dien-2-yl)pyridine [ No CAS ]
  • [ 153624-38-5 ]
  • (Z)-2-(3-(4-isobutylphenyl)but-2-en-2-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate; silver(l) oxide In ethanol at 100℃; for 36h; Inert atmosphere; Schlenk technique;
  • 73
  • [ 153624-38-5 ]
  • C20H26N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; toluene 2: triethylamine / methanol 3: sodium cyanoborohydride / methanol
  • 74
  • [ 153624-38-5 ]
  • C20H24N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; toluene 2: triethylamine / methanol
  • 75
  • [ 153624-38-5 ]
  • C20H26N2O*CH4O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; toluene 2: triethylamine / methanol 3: sodium cyanoborohydride / methanol 4: ethyl acetate
  • 76
  • [ 153624-38-5 ]
  • [ 1330681-32-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: acetonitrile; water / 20 °C 1.2: 20 °C / Heating 2.1: acetonitrile / 1 h / 65 °C 3.1: water; dichloromethane
  • 77
  • [ 153624-38-5 ]
  • C19H24I(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetonitrile; water / 20 °C 1.2: 20 °C / Heating 2.1: acetonitrile / 1 h / 65 °C
  • 78
  • potassium fluoride [ No CAS ]
  • [ 153624-38-5 ]
  • C10H13BF3(1-)*K(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: potassium fluoride; 4-isobutyl-phenylboronic acid In water; acetonitrile at 20℃; Stage #2: With tartaric acid In tetrahydrofuran; water; acetonitrile at 20℃; Heating;
  • 79
  • [ 15973-65-6 ]
  • [ 153624-38-5 ]
  • (E)-3-(4-isobutylphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With copper (II) acetate; palladium diacetate In dimethyl sulfoxide at 70℃; for 2h; chemoselective reaction;
  • 80
  • 14-aminotetrandrine [ No CAS ]
  • [ 153624-38-5 ]
  • 14-(4-isobutylanilino)tetrandrine [ No CAS ]
YieldReaction ConditionsOperation in experiment
82.6% With pyridine; copper (II) acetate In dichloromethane at 20℃; 7 Example 7: Preparation of 14- (4-isobutylaniline)-tetrandrine. Take an appropriate amount of 14-aminotetrandrine, add pyridine, copper acetate and 4-isobutylphenylboronic acid, stir the reaction at room temperature for a certain time, anhydrous sodium sulfate drying, steaming dry, to give 14- (4-isobutylaniline)-tetrandrine.The product was a yellow-brown solid with a yield of 82.6%.
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