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[ CAS No. 202865-85-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 202865-85-8
Chemical Structure| 202865-85-8
Chemical Structure| 202865-85-8
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Quality Control of [ 202865-85-8 ]

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Product Details of [ 202865-85-8 ]

CAS No. :202865-85-8 MDL No. :MFCD00070749
Formula : C7H6BrI Boiling Point : -
Linear Structure Formula :- InChI Key :QSQOGKONVJDRNH-UHFFFAOYSA-N
M.W : 296.93 Pubchem ID :2735574
Synonyms :

Calculated chemistry of [ 202865-85-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.83
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.53
Log Po/w (XLOGP3) : 3.63
Log Po/w (WLOGP) : 3.36
Log Po/w (MLOGP) : 4.25
Log Po/w (SILICOS-IT) : 3.95
Consensus Log Po/w : 3.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.46
Solubility : 0.0103 mg/ml ; 0.0000346 mol/l
Class : Moderately soluble
Log S (Ali) : -3.32
Solubility : 0.143 mg/ml ; 0.000481 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.58
Solubility : 0.00786 mg/ml ; 0.0000265 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.86

Safety of [ 202865-85-8 ]

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 [ 202865-85-8 ]

* 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 [ 202865-85-8 ]

[ 202865-85-8 ] Synthesis Path-Downstream   1~101

  • 3
  • [ 627-19-0 ]
  • [ 202865-85-8 ]
  • 1-bromo-2-methyl-4-pent-1-ynyl-benzene [ No CAS ]
  • 4
  • [ 616-45-5 ]
  • [ 202865-85-8 ]
  • 1-(4-bromo-3-methylphenyl)pyrrolidin-2-one [ No CAS ]
  • 5
  • [ 53937-02-3 ]
  • [ 202865-85-8 ]
  • [ 959960-95-3 ]
YieldReaction ConditionsOperation in experiment
80% With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; N,N-dimethyl-formamide; at 180℃; for 0.25h;Microwave irradiation; A mixture of 4-benzyloxy-2(lH)-pyridone (50 mg, 0.0025 mol), <strong>[202865-85-8]2-bromo-5-iodotoluene</strong> (1.13 g, 0.0038 mol), CuI (0.238 g, 0.0015 mol), N,N-dimethylethylenediamine (0.266 ml, 0.0025 mol), and K3PO4 (1.06 g, 0.005 mol) in dioxane/DMF 9:1 (75 ml) was stirred at 180 0C in a microwave for 15 minutes Then, DCM was added. The solid was filtered off through dicalite and the filtrate was washed with NH4OH 32 %. The organic layer was separated, dried over Na2SO4 and the solvent was evaporated. The residue was purified by column chromatography (eluent: DCM). The desired product was collected and evaporated. The resulting product was precipitated with DIPE yielding 0.737 g of intermediate compound 1-11 (80 %).
70% Al l. Preparation of intermediate I- 11; 1-11 A mixture of 4-benzyloxy-2(lH)-pyridone (0.100 g, 0.50 mmol), <strong>[202865-85-8]2-bromo-5-iodotoluene</strong> (0223 g, 0.75 mmol), CuI (0.048 g, 0.25 mmol), N,N'-dimethylethylenediamine (0.053 ml, 0.5 mmol) and K3PO4 (0.212 g, 1.0 mmol) in dioxane/DMF (4/1) was heated for 15 minutes at 180 0C in a microwave oven. Then DCM was added. The solid was filtered off through a CELITE pad and to the filtrate, a 32 % NH3 solution was added. The organic layer was separated, washed with brine, dried (Na2SO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: DCM). The product fractions were collected and the solvent was evaporated. The residue was treated with DIPE to yield intermediate compound 1-11 (0.130 g, 70 %).
  • 6
  • [ 97674-02-7 ]
  • [ 202865-85-8 ]
  • C11H13BrO [ No CAS ]
YieldReaction ConditionsOperation in experiment
bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 80℃; for 17h;Product distribution / selectivity; PdCl2(Ph3P)2 (257 mg, 0.367 mmol) was added to a dioxane (45 mL) solution of <strong>[202865-85-8]1-bromo-4-iodo-2-methylbenzene</strong> (3.01 g, 10.13 mmol) and tri-n-butyl(1-ethoxyvinyl)stannane (3.826 g, 10.59 mmol) and heated at 80 C. for 17 hours. The reaction mixture was treated with water (15 mL), cooled to 0 C. (ice/water), and then NBS (1.839 g, 10.3 mmol) was added in batches over 7 minutes. After about 25 minutes of stirring, the volatile component was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2, and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified by a gravity chromatography (silica gel; 4% ethyl acetate/hexanes)to provide bromide 121a as a brownish-yellow solid (2.699 g); the sample is impure and contains stannane-derived impurities, among others. 1H NMR (CDCl3, delta=7.24, 400 MHz): 7.83 (s, 1H), 7.63 (s, 2H), 4.30 (s, 2H), 2.46 (s, 3H).; PdCl2(Ph3P)2 (257 mg, 0.367 mmol) was added to a dioxane (45 mL) solution of <strong>[202865-85-8]1-bromo-4-iodo-2-methylbenzene</strong> (3.01 g, 10.13 mmol) and tri-n-butyl(1-ethoxyvinyl)stannane (3.826 g, 10.59 mmol) and heated at 80 C. for 17 hr. The reaction mixture was treated with water (15 mL), cooled to 0 C. (ice/water), and then NBS (1.839 g, 10.3 mmol) was added in batches over 7 min. About 25 min of stirring, the volatile component was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2, and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified by a gravity chromatography (silica gel; 4% EtOAc/hexanes)to afford bromide 136a as a brownish-yellow solid (2.699 g); the sample is impure and contains stannane-derived impurities, among others. 1H NMR (CDCl3, delta=7.24, 400 MHz): 7.83 (s, 1H), 7.63 (s, 2H), 4.30 (s, 2H), 2.46 (s, 3H).
bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 80℃; for 17h; Example 121, Step a-bPdCl2(Ph3P)2 (257 mg, 0.367 mmol) was added to a dioxane (45 mL) solution of l-bromo-4-iodo-2-methylbenzene (3.01 g, 10.13 mmol) and tri-«-butyl(l- ethoxyvinyl)stannane (3.826 g, 10.59 mmol) and heated at 80 0C for ~17 hours. The reaction mixture was treated with water (15 mL), cooled to ~0 0C (ice/water), and <n="130"/>then NBS (1.839 g, 10.3 mmol) was added in batches over 7 minutes. After about 25 minutes of stirring, the volatile component was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2, and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified by a gravity chromatography (silica gel; 4% ethyl acetate/hexanes)to provide bromide 121a as a brownish-yellow solid (2.699 g); the sample is impure and contains stannane-derived impurities, among others. 1H NMR (CDCl3, delta = 7.24, 400 MHz): 7.83 (s, IH), 7.63 (s, 2H), 4.30 (s, 2H), 2.46 (s, 3H).
  • 7
  • [ 97674-02-7 ]
  • [ 202865-85-8 ]
  • [ 3114-08-7 ]
YieldReaction ConditionsOperation in experiment
Example N22, Step aA solution of l-bromo-4-iodo-2-methylbenzene (5.0 g, 16.83 mmol) in dioxane (75 mL) was purged with 2 for 10 minutes. Then PdCl2(Pli3P)2 (428 mg 0.609 mmol) and tri-n-butyl(l-ethoxyvinyl)stanane (5.94 mL, 17.59 mmol) was added, and the reaction mixture was purged with 2 for 10 minutes and heated at 80 C for overnight. Water (25 mL) was added to the reaction mixture and cooled to 0 C, NBS (3 g, 17.1 mmol) was added and the mixture was stirred for 30 minutes. The volatile component was removed under reduced pressure, and water was added to the resulting residue and it was extracted with DCM (3 x 100 mL). The combined organic extract was dried over Na2S04 and concentrated in vacuo. The crude was purified by flash chromatography (ISCO; EtOAc: petroleum ether, 2:98) to afford ketone N22a (2.6 g). ¾ NMR (CDCI3, delta = 7.26 ppm, 400 MHz): delta 7.84 (d, J = 0.8, 1H), 7.65-7.62 (m, 2H), 4.32 (s, 2H), 2.48 (s, 3H).
PdCl2(Ph3P)2 (257 mg, 0.367 mmol) was added to a dioxane (45 mL) solution of <strong>[202865-85-8]1-bromo-4-iodo-2-methylbenzene</strong> (3.01 g, 10.13 mmol) and tri-n-butyl(1-ethoxyvinyl)stannane (3.826 g, 10.59 mmol) and heated at 80 C. for 17 hours. The reaction mixture was treated with water (15 mL), cooled to 0 C. (ice/water), and then NBS (1.839 g, 10.3 mmol) was added in batches over 7 minutes. After about 25 minutes of stirring, the volatile component was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2, and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified by a gravity chromatography (silica gel; 4% ethyl acetate/hexanes) to provide bromide 121a as a brownish-yellow solid (2.699 g); the sample is impure and contains stannane-derived impurities, among others. 1H NMR (CDCl3, delta=7.24, 400 MHz): 7.83 (s, 1H), 7.63 (s, 2H), 4.30 (s, 2H), 2.46 (s, 3H).
  • 8
  • [ 202865-85-8 ]
  • [ 3114-08-7 ]
YieldReaction ConditionsOperation in experiment
PdCl2(Ph3P)2 (257 mg, 0.367 mmol) was added to a dioxane (45 mL) solution of <strong>[202865-85-8]1-bromo-4-iodo-2-methylbenzene</strong> (3.01 g, 10.13 mmol) and tri-n-butyl(1-ethoxyvinyl)stannane (3.826 g, 10.59 mmol) and heated at 80 C. for 17 hours. The reaction mixture was treated with water (15 mL), cooled to 0 C. (ice/water), and then NBS (1.839 g, 10.3 mmol) was added in batches over 7 minutes. After about 25 minutes of stirring, the volatile component was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2, and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified by a gravity chromatography (silica gel; 4% ethyl acetate/hexanes)to provide bromide 121a as a brownish-yellow solid (2.699 g); the sample is impure and contains stannane-derived impurities, among others. 1H NMR (CDCl3, delta=7.24, 400 MHz): 7.83 (s, 1H), 7.63 (s, 2H), 4.30 (s, 2H), 2.46 (s, 3H). Example 136 Step a and b PdCl2(Ph3P)2 (257 mg, 0.367 mmol) was added to a dioxane (45 mL) solution of <strong>[202865-85-8]1-bromo-4-iodo-2-methylbenzene</strong> (3.01 g, 10.13 mmol) and tri-n-butyl(1-ethoxyvinyl)stannane (3.826 g, 10.59 mmol) and heated at 80 C. for 17 hr. The reaction mixture was treated with water (15 mL), cooled to 0 C. (ice/water), and then NBS (1.839 g, 10.3 mmol) was added in batches over 7 min. About 25 min of stirring, the volatile component was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2, and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified by a gravity chromatography (silica gel; 4% EtOAc/hexanes) to afford bromide 136a as a brownish-yellow solid (2.699 g); the sample is impure and contains stannane-derived impurities, among others. 1H NMR (CDCl3, delta=7.24, 400 MHz): 7.83 (s, 1H), 7.63 (s, 2H), 4.30 (s, 2H), 2.46 (s, 3H).
  • 9
  • [ 79887-14-2 ]
  • [ 202865-85-8 ]
  • 2-methyl-4-(4-ethoxyphenylethynyl)bromobenzene [ No CAS ]
  • 10
  • [ 202865-85-8 ]
  • 1-bromo-2-methyl-4-pentyl-benzene [ No CAS ]
  • 11
  • [ 202865-85-8 ]
  • C14H23BO2 [ No CAS ]
  • 12
  • [ 202865-85-8 ]
  • C12H19BO2 [ No CAS ]
  • 13
  • [ 202865-85-8 ]
  • 2-cyano-6-(2-methyl-4-pentylphenyl)naphthalene [ No CAS ]
  • 14
  • [ 202865-85-8 ]
  • 2-methyl-4-pentyl-4''-cyano-1,1':4',1''-terphenyl [ No CAS ]
  • 15
  • [ 202865-85-8 ]
  • [ 289617-99-8 ]
  • 16
  • [ 202865-85-8 ]
  • [ 289618-00-4 ]
  • 17
  • [ 202865-85-8 ]
  • [ 289618-03-7 ]
  • 18
  • [ 79099-07-3 ]
  • [ 202865-85-8 ]
  • [ 227304-98-5 ]
YieldReaction ConditionsOperation in experiment
64% With n-butyllithium; In tetrahydrofuran; hexane; pentane; B. A 2.5M solution of n-butyllithium in hexane (38 ml, 94 mmol) was added over about 10 minutes to a stirred mixture of <strong>[202865-85-8]2-bromo-5-iodo-toluene</strong> (28 g, 94 mmol) in anhydrous ether (500 ml), under nitrogen, at about -75 C. After a further 15 minutes, a solution of t-butyl 4-oxopiperidine-1-carboxylate (17 g, 85 mmol) in anhydrous tetrahydrofuran (50 ml) was added at such a rate that the reaction temperature was maintained below -60 C. The reaction mixture was stirred at about -75 C. for 1 hour, allowed to warm to 0 C. and quenched with aqueous ammonium chloride solution. The organic phase was separated, washed with water, dried (MgSO4) and evaporated under reduced pressure. The residue was dissolved in pentane and the resulting solution cooled to 0 C., when the title compound crystallized. It was collected and dried to afford a colourless solid (20.1 g, 64%), identical with that obtained in Preparation 33A.
  • 19
  • [ 444892-03-9 ]
  • [ 202865-85-8 ]
  • [ 1018829-32-7 ]
  • 20
  • [ 132871-12-6 ]
  • [ 202865-85-8 ]
  • [ 1018829-31-6 ]
  • 21
  • [ 204327-96-8 ]
  • [ 202865-85-8 ]
  • [ 1018829-33-8 ]
  • 22
  • [ 141-32-2 ]
  • [ 202865-85-8 ]
  • [ 1402975-31-8 ]
  • 23
  • [ 5419-55-6 ]
  • [ 202865-85-8 ]
  • C13H20BBrO2 [ No CAS ]
  • 26
  • [ 202865-85-8 ]
  • rac-tert-butyl (3S,4R)-4-[2-(1,3-dioxolan-2-yl)-4,5-difluorophenyl]-4-hydroxy-3-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1-piperidinecarboxylate [ No CAS ]
  • 27
  • [ 202865-85-8 ]
  • rac-tert-butyl (1R,3'S)-5,6-difluoro-3-hydroxy-3'-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 28
  • [ 202865-85-8 ]
  • rac-tert-butyl (3S,4R)-4-[4,5-difluoro-2-(hydroxymethyl)phenyl]-4-hydroxy-3-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1-piperidinecarboxylate [ No CAS ]
  • 29
  • [ 202865-85-8 ]
  • rac-tert-butyl (1R,3'S)-5,6-difluoro-3'-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 30
  • [ 202865-85-8 ]
  • rac-tert-butyl (1R,3'S)-5,6-difluoro-3'-[2'-(hydroxymethyl)-3-methyl-4-biphenylyl]-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 31
  • [ 202865-85-8 ]
  • rac-(1R,3'S)3'-[2'-(tert-butoxymethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3H-spiro[2-benzofuran-1,4'-piperidine] [ No CAS ]
  • 32
  • [ 202865-85-8 ]
  • rac-{4'-[(1R,3'S)-5,6-difluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3'-yl]-3'-methyl-2-biphenylyl}methanol [ No CAS ]
  • 33
  • [ 202865-85-8 ]
  • rac-tert-butyl (1R,3'S)-(5,6-difluoro-3'-(3-methyl-2'-[methylsulfonyl]oxy}methyl)-4-biphenylyl)-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 34
  • [ 202865-85-8 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(cyanomethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 35
  • [ 202865-85-8 ]
  • rac-{4'-[(1R,3'S)-5,6-difluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3'-yl]-3'-methyl-2-biphenylyl}acetonitrile [ No CAS ]
  • 36
  • [ 202865-85-8 ]
  • rac-tert-butyl (1R,3'S)-3,-{2'-[2-(acetylamino)ethyl]-3-methyl-4-biphenylyl}-5,6-difluoro-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 37
  • [ 202865-85-8 ]
  • C32H36F2N2O3 [ No CAS ]
  • 38
  • [ 202865-85-8 ]
  • rac-N-(2-{4'-[(1R,3'S)-5,6-difluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3'-yl]-3'-methyl-2-biphenylyl}ethyl)acetamide [ No CAS ]
  • 39
  • [ 202865-85-8 ]
  • rac-tert-butyl (3S,4R)-4-hydroxy-4-(2-methoxy-5-[(triisopropylsilyl)oxy]methyl}-4-pyridinyl)-3-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1-piperidinecarboxylate [ No CAS ]
  • 40
  • [ 202865-85-8 ]
  • rac-tert-butyl (3S,4R)-4-hydroxy-4-[5-(hydroxymethyl)-2-methoxy-4-pyridinyl]-3-[2'-(hydroxymethyl)-3-methyl-4-biphenylyl]-1-piperidinecarboxylate [ No CAS ]
  • 41
  • [ 202865-85-8 ]
  • rac-tert-butyl (1R,3'S)-6-methoxy-3'-(3-methyl-2'-[(methylsulfonyl)oxy]methyl}-4-biphenylyl)-1'H,3H-spiro[furo[3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 42
  • [ 202865-85-8 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(iodomethyl)-3-methyl-4-biphenylyl]-6-methoxy-1H,3H-spiro[furo[3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 43
  • [ 202865-85-8 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(3-tert-butoxy-3-oxopropyl)-3-methyl-4-biphenylyl]-6-methoxy-1'H,3H-spiro[furo [3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 44
  • [ 202865-85-8 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(3-hydroxypropyl)-3-methyl-4-biphenylyl]-6-methoxy-1'H,3H-spiro[furo[3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 45
  • [ 202865-85-8 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(3-methoxypropyl)-3-methyl-4-biphenylyl]-5-methyl-6-oxo-5,6-dihydro-1H,3H-spiro[furo[3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 46
  • [ 202865-85-8 ]
  • rac-(1R,3'S)-3'-[2'-(3-methoxypropyl)-3-methyl-4-biphenylyl]-5-methyl-3,5-dihydro-6H-spiro[furo[3,4-c]pyridine-1,4'-piperidin]-6-one [ No CAS ]
  • 47
  • [ 202865-85-8 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(5-tert-butoxy-3,5-dioxopentyl)-3-methyl-4-biphenylyl]-6-methoxy-1H,3H-spiro[furo[3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 48
  • [ 202865-85-8 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(5-tert-butoxy-3,5-dioxopentyl)-3-methyl-4-biphenylyl]-5-methyl-6-oxo-5,6-dihydro-1H,3H-spiro[furo[3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 49
  • [ 202865-85-8 ]
  • rac-(1R,3'S)-5-methyl-3'-[3-methyl-2'-(3-oxobutyl)-4-biphenylyl]-3,5-dihydro-6H-spiro[furo[3,4-c]pyridine-1,4'-piperidin]-6-one [ No CAS ]
  • 50
  • [ 5735-41-1 ]
  • [ 202865-85-8 ]
  • [ 1307795-18-1 ]
YieldReaction ConditionsOperation in experiment
To a 2:1 (v/v) toluene: ethanol solution (0.25 M) of 2,l-benzoxaborol-l(3H)-ol (1 eq.) and <strong>[202865-85-8]2-bromo-5-iodotoluene</strong> (1.2 eq.) was added was added trans- bis(triphenylphosphine) palladium(II) bromide (0.02 eq.). The vessel was repeatedly evacuated and back-filled with nitrogen. Finally, Na2C03 (2 M aq. solution, 3 eq.) was added and the resulting mixture was heated at 50 C for 12 h. The now black suspension was cooled to RT, diluted with ether and quenched with 10% aq. HC1. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed further with 1 N aq. NaOH, water and brine, dried over Na2S04, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (Si02, Hex - 1 :1 (v/v) Hex: EtOAc) afforded the title compound as a golden, yellow oil.
  • 51
  • [ 887234-98-2 ]
  • [ 202865-85-8 ]
  • [ 1307795-56-7 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;[PdBr2(PPh3)2]; In ethanol; toluene; at 50℃; for 12h;Inert atmosphere; To a 2:1 (v/v) toluene: ethanol solution (0.034 M) of methyl 3-methyl-2 -(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yI)benzoate (1 eq.) from the previous step and 2- bromo-5-iodotoluene (1.2 eq.) was added was added trans-bis(triphenylphospliine) palladium(II) bromide (0.12 eq.). The vessel was repeatedly evacuated and back-filled with nitrogen. Finally, Na2C03 (2 M aq. solution, 3 eq.) was added and the resulting mixture was heated at 50 C for 12 h. The now black suspension was cooled to RT, diluted with ether and quenched with 10% aq. HC1. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed further with 1 N aq. NaOH, water and brine, dried over Na2S04, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (Si02, Hex -> 1 :1 (v/v) Hex: EtOAc) afforded the title compound as a colorless oil.
  • 52
  • [ 154962-37-5 ]
  • [ 202865-85-8 ]
  • [ 1239227-04-3 ]
  • 53
  • [ 202865-85-8 ]
  • [ 1239227-07-6 ]
  • 54
  • [ 202865-85-8 ]
  • [ 1239227-10-1 ]
  • 55
  • [ 202865-85-8 ]
  • C39H36O5 [ No CAS ]
  • 56
  • [ 202865-85-8 ]
  • [ 1239227-16-7 ]
  • 57
  • [ 1692-25-7 ]
  • [ 202865-85-8 ]
  • [ 1359945-06-4 ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; for 24h;Inert atmosphere; Reflux; General procedure: To a stirred solution of 6-bromo-3-pyridyl boronic acid (1.25 equiv, 847 mg, 4.20 mmol) in 1,4-dioxane (30 mL) under nitrogen were added 5-bromo-2-iodotoluene (1 g, 3.36 mmol) and tetrakis-(triphenylphosphine)palladium(0) (0.05 equiv, 195 mg, 0.17 mmol). After 5 min of stirring, aqueous Na2CO3 (2.5 equiv, 892 mg, 8.42 mmol) in 5 mL of water was added. Then the mixture was heated to 80 C until the starting material was consumed (TLC). After cooling down to room temperature, the mixture was filtered on Celite and washed with CH2Cl2. The aqueous layer was extracted with EtOAc (2×50 mL). Combined organic layers were washed with saturated aqueous solution of NaCl (50 mL), and dried over MgSO4. Solvent was removed in vacuo and crude product was purified by column chromatography, with 99:1 cyclohexane/EtOAc affording 3c as a white solid (520 mg, 47%).
  • 58
  • [ 202865-85-8 ]
  • [ 1359945-08-6 ]
  • 60
  • [ 202865-85-8 ]
  • [ 1359945-12-2 ]
  • [ 1359945-16-6 ]
  • 61
  • [ 202865-85-8 ]
  • [ 1359945-14-4 ]
  • [ 1359945-18-8 ]
  • 62
  • [ 202865-85-8 ]
  • [ 444120-91-6 ]
  • [ 1359945-04-2 ]
YieldReaction ConditionsOperation in experiment
83% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; for 24h;Inert atmosphere; Reflux; General procedure: To a stirred solution of 6-bromo-3-pyridyl boronic acid (1.25 equiv, 847 mg, 4.20 mmol) in 1,4-dioxane (30 mL) under nitrogen were added 5-bromo-2-iodotoluene (1 g, 3.36 mmol) and tetrakis-(triphenylphosphine)palladium(0) (0.05 equiv, 195 mg, 0.17 mmol). After 5 min of stirring, aqueous Na2CO3 (2.5 equiv, 892 mg, 8.42 mmol) in 5 mL of water was added. Then the mixture was heated to 80 C until the starting material was consumed (TLC). After cooling down to room temperature, the mixture was filtered on Celite and washed with CH2Cl2. The aqueous layer was extracted with EtOAc (2×50 mL). Combined organic layers were washed with saturated aqueous solution of NaCl (50 mL), and dried over MgSO4. Solvent was removed in vacuo and crude product was purified by column chromatography, with 99:1 cyclohexane/EtOAc affording 3c as a white solid (520 mg, 47%).
  • 63
  • [ 87199-14-2 ]
  • [ 202865-85-8 ]
  • [ 1307795-18-1 ]
  • 64
  • [ 202865-85-8 ]
  • [ 1366038-33-6 ]
  • 65
  • [ 202865-85-8 ]
  • C40H53F2NO6Si [ No CAS ]
  • 66
  • [ 202865-85-8 ]
  • C40H51F2NO5Si [ No CAS ]
  • 67
  • [ 202865-85-8 ]
  • C31H31F2NO5 [ No CAS ]
  • 68
  • [ 202865-85-8 ]
  • C32H33F2NO7S [ No CAS ]
  • 69
  • [ 202865-85-8 ]
  • C32H30F2N2O4 [ No CAS ]
  • 70
  • [ 202865-85-8 ]
  • C32H34F2N2O4 [ No CAS ]
  • 71
  • [ 202865-85-8 ]
  • [ 1307795-85-2 ]
  • C34H36F2N2O5 [ No CAS ]
  • 72
  • [ 202865-85-8 ]
  • C31H35F2NO5 [ No CAS ]
  • 73
  • [ 202865-85-8 ]
  • C32H36F2N2O3 [ No CAS ]
  • 74
  • [ 202865-85-8 ]
  • C34H38F2N2O4 [ No CAS ]
  • C34H38F2N2O4 [ No CAS ]
  • 75
  • [ 202865-85-8 ]
  • [ 1307796-10-6 ]
  • 76
  • [ 202865-85-8 ]
  • [ 1253925-61-9 ]
  • 77
  • [ 141-43-5 ]
  • [ 202865-85-8 ]
  • [ 1020970-64-2 ]
YieldReaction ConditionsOperation in experiment
81% With potassium carbonate;copper(l) iodide; L-proline; In dimethyl sulfoxide; at 60℃; for 12h; A mixture of <strong>[202865-85-8]2-bromo-5-iodotoluene</strong> (1.60 g, 5.40 mmol), 2-aminoethanol (0.49 mL, 8.14 mmol), CuI (53.3 mg, 0.28 mmol), L-proline (63.4 mg, 0.55 mmol) and K2CO3 (1.49 g, 10.8 mmol) in DMSO (3.24 mL) was stirred at 60C for 12 hours. The reaction mixture was cooled and then diluted with AcOEt, and the organic layer was sequentially washed with H2O and saturated brine. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/AcOEt = 1/1) to give 2-(4-bromo-3-methyl-phenylamino)-ethanol as a brown solid (1.00 g, 81%). MS (ESI) m/z = 230, 232 (M+H)+.
  • 78
  • [ 22677-21-0 ]
  • [ 202865-85-8 ]
  • [ 1253926-33-8 ]
YieldReaction ConditionsOperation in experiment
38% With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃;Inert atmosphere; A mixture of <strong>[202865-85-8]2-bromo-5-iodotoluene</strong> (500 mg, 1.68 mmol), (R)-4-hydroxy-pyrrolidinone (204 mg, 2.02 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (58.5 mg, 0.101 mmol), tris(dibenzylideneacetone)-dipalladium(0)-chloroform adduct (35.0 mg, 0.034 mmol) and cesium carbonate (769 mg, 2.36 mmol) in 1,4-dioxane (degassed, 5 ml) was stirred at 110C overnight in a nitrogen stream. The reaction mixture was treated with H2O and extracted with AcOEt (x 2). The organic layers were combined and sequentially washed with H2O and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (n-hexane/AcOEt) to give (R)-1-(4-bromo-3-methyl-phenyl)-4-hydroxy-pyrrolidin-2-one as a pale brown solid (173 mg, 38%) 1H-NMR (400 MHz, DMSO-d6) delta 2.29 (1H, d, J = 17.1 Hz), 2.34 (3H, s), 2.82 (1H, dd, J = 17.1, 6.4 Hz), 3.57 (1H, d, J = 10.3 Hz), 4.01 (1H, dd, J = 10.3, 4.9 Hz), 4.36-4.40 (1H, m), 5.35 (1H, d, J = 3.4 Hz, OH), 7.51 (1H, dd, J = 8.8, 2.4 Hz), 7.55 (1H, d, J = 8.8 Hz), 7.62 (1H, br. s). MS (ESI) m/z = 270, 272 (M+H)+.
  • 79
  • [ 202865-85-8 ]
  • [ 1337533-59-1 ]
  • 80
  • [ 202865-85-8 ]
  • [ 1359945-14-4 ]
  • 81
  • [ 202865-85-8 ]
  • [ 1400742-95-1 ]
  • 82
  • [ 202865-85-8 ]
  • [ 1400742-96-2 ]
  • 83
  • [ 202865-85-8 ]
  • [ 1400742-97-3 ]
  • 84
  • [ 202865-85-8 ]
  • [ 1400742-91-7 ]
  • 85
  • [ 202865-85-8 ]
  • [ 1400742-92-8 ]
  • 86
  • [ 202865-85-8 ]
  • C13H9Br3 [ No CAS ]
  • 87
  • [ 202865-85-8 ]
  • [ 1237107-66-2 ]
  • 88
  • [ 202865-85-8 ]
  • C17H11Br3 [ No CAS ]
  • 89
  • [ 202865-85-8 ]
  • [ 1400743-08-9 ]
  • 90
  • [ 202865-85-8 ]
  • [ 1400742-93-9 ]
  • 91
  • [ 202865-85-8 ]
  • C14H11Br3O [ No CAS ]
  • 92
  • [ 202865-85-8 ]
  • [ 1400743-09-0 ]
  • 93
  • [ 202865-85-8 ]
  • [ 98-80-6 ]
  • [ 92022-07-6 ]
  • 94
  • [ 13922-41-3 ]
  • [ 202865-85-8 ]
  • C17H13Br [ No CAS ]
  • 95
  • [ 5720-07-0 ]
  • [ 202865-85-8 ]
  • [ 934759-17-8 ]
  • 96
  • [ 1396007-85-4 ]
  • [ 202865-85-8 ]
  • [ 1423703-99-4 ]
YieldReaction ConditionsOperation in experiment
59.6% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere; To a solution of compound LXXXVI-1 (1.5 g, 4.9 mmol) in DME:H20 = 3: 1 (20 mL), Na2C03 (1.05 g, 9.9mmol) and compound LXXXVI-1A (1.47 mg, 4.9 mmol) were added, the resulting mixture was purged with nitrogen, then Pd (dppf)Cl2 (182 mg, 0.2 mmol) was added. The reaction mixture was stirred at 80 C overnight under nitrogen protection. After completion of the reaction, the mixture was poured into water, extract with EtOAc (30 mL x 3), the combined organic layers were dried over Na2S04, concentrated in vacuo. The residue was purified by chromatography (PE:EA = 100: 1) to afford compound LXXXVI-2 (1.06 g , yield 59.6%).
  • 97
  • [ 202865-85-8 ]
  • [ 197449-60-8 ]
  • 98
  • [ 202865-85-8 ]
  • [ 197450-40-1 ]
  • 99
  • [ 202865-85-8 ]
  • [ 1492902-05-2 ]
  • 100
  • [ 202865-85-8 ]
  • [ 1492902-19-8 ]
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