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CAS No. : | 13534-90-2 | MDL No. : | MFCD00234016 |
Formula : | C5H3Br2N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZFZWZGANFCWADD-UHFFFAOYSA-N |
M.W : | 236.89 | Pubchem ID : | 817106 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 39.64 |
TPSA : | 12.89 Ų |
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) : | -6.16 cm/s |
Log Po/w (iLOGP) : | 1.87 |
Log Po/w (XLOGP3) : | 2.23 |
Log Po/w (WLOGP) : | 2.61 |
Log Po/w (MLOGP) : | 2.01 |
Log Po/w (SILICOS-IT) : | 2.8 |
Consensus Log Po/w : | 2.31 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.27 |
Solubility : | 0.128 mg/ml ; 0.000539 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.14 |
Solubility : | 1.73 mg/ml ; 0.00731 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.74 |
Solubility : | 0.0435 mg/ml ; 0.000184 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.44 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In N,N-dimethyl-formamide; at 20℃; for 1h;Inert atmosphere; | To a solution of <strong>[13534-90-2]3,4-dibromopyridine</strong> (500 mg; 2.11 mmol; 1 eq.) in dry DMF (2 mL) sodium methanethionalate (163 mg; 2.32 mmol; 1.1 eq.) is added portionwise under Ar. After stirring at room temperature for 1 h, the reaction mixture is diluted with EtOAc and the organic layer is washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue is purified by FCC (0-50% EtOAc gradient in hexane) to give 3-bromo-4- (methylsulfanyl)pyridine (370 mg; 1.81 mmol; yield: 86%; light yellow oil; UPLC purity: 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 55 4-[(3-Bromo-pyridin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester A mixture of benzyl-4-(aminomethyl)piperidine-1-carboxylate (EXAMPLE 13, Step 1, 0.20 g, 0.81 mmol), <strong>[13534-90-2]3,4-dibromo-pyridine</strong> (Chem. Abstracts, 58:5627) (0.19 g, 0.81 mmol) in IPA (0.5 mL) was heated at 100 C. in a sealed reaction tube for 7 h, then concentrated in vacuo. The residue was purified by silica gel chromatography (DCM IPA hexane)) to give 4-[(3-Bromo-pyridin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester. M.S.(M+1):405.27. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1 g | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In ethanol; water; for 3h;Reflux; Inert atmosphere; | A mixture of 4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-lH-pyrrole-2-carboxylic acid methyl ester (2.5 g, 10 mmol), <strong>[13534-90-2]3,4-dibromo-pyridine</strong> (2.6 g, 11 mmol), CS2CO3 (6.5 g, 20 mmol) and Pd(dppf)Cl2 (732 mg, 1 mmol) in EtOH (30 mL) and water (5 mL) was refluxed for 3 hours under N2 protection, and then poured into water (100 mL). The aqueous layer was extracted with EtOAc (100 mLx5). The combined organic layers were concentrated. The residue was purified by flash chromatography to give 4-(3-bromo-pyridin-4-yl)-lH-pyrrole-2-carboxylic acid methyl ester (1 g) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With tetrakis(triphenylphosphine) palladium(0); at 90℃; for 2.5h;Inert atmosphere; | Step I: A solution of cyclopropyl zink bromide (0.5 M, 12 mL, 6.0 mmol) was added to ethyl <strong>[13534-90-2]3,4-dibromopyridine</strong> (1.42 g, 6.0 mmol) and Pd(PPh3)4 (347 mg, 0.6 mmol) and the RM was stirred at 90 Cunder an inert atmosphere for 2.5 h. Subsequently, the volatiles were removed under reduced pressure and the residue was dissolved in water and extracted with CH2CI2. The combined organic layers were dried and the volatiles were removed under reduced pressure. The residue was purified by CC (SiC2, EtOAc/Cy (1:2)) to yield the desired compound (600 mg, 51%).LC-MS (Method 1): m/z [M+H] = 198.1 (MW calc. = 196.98); R1 = 2.6 mm. 1H-NMR (CDCI3): oe = 0.79 (m,2H); 1.15 (m, 2H); 2.20 (m, 1H); 6.72 (d, J = 5.2 H, 1H); 8.85 (d, J = 5.2 Hz, IH); 8.63 (s, 1H). 13C-NMR(CDCI3): oe = 9.7; 15.2; 119.9; 123.9; 148.1; 151.3; 152.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
455 mg | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In water; dimethyl sulfoxide; | The titled compound was prepared by the reaction of <strong>[13534-90-2]3,4-dibromopyridine</strong> (1.01 g, 4.26 mmol) with 4-nitrophenylboronic acid pinacol ester (1.06 g, 4.26 mmol) using cesium carbonate (2.07 g, 6.39 mmol) and [l, -bis(diphenylphosphino)ferrocene]dichloropalladium (II) (155 mg, 0.21 mmol) in a mixture of DMSO and water (20 mL, 3: 1) as per the procedure described in Step 1 of Intermediate 1 to yield 455 mg of the product; 1H NMR (300 MHz, CDC13) delta 7.33 (d, 7 = 4.8 Hz, 1H), 7.63 (d, 7 = 8.7 Hz, 2H), 8.35 (d, 7 = 8.7 Hz, 2H), 8.64 (d, 7 = 5.1 Hz, 1H), 8.89 (s, 1H) ; ESI-MS (m/z) 281 (M+2H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
513 mg | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In water; dimethyl sulfoxide; | The titled compound was prepared by the reaction of <strong>[13534-90-2]3,4-dibromopyridine</strong> (1.02 g, 4.30 mmol) with 4-chlorophenylboronic acid (673 mg, 4.30 mmol) using cesium carbonate (2.10 g, 6.45 mmol) and [l, -bis(diphenylphosphino)ferrocene]dichloropalladium (II) (157 mg, 0.22 mmol) in a mixture of DMSO and water (20 mL, 3: 1) as per the procedure described in Step 1 of Intermediate 1 to yield 513 mg of the product; 1H NMR (300 MHz, CDC13) delta 7.25 (d, J = 6.9 Hz, 1H), 7.37 (d, J = 8.4 Hz, 2H), 7.44 (d, J = 8.4 Hz, 2H), 8.54 (d, J = 5.1 Hz, 1H), 8.81 (s, 1H); APCI-MS (m/z) 268 (M)+, 270 (M+2H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; at -78 - 24℃; for 12h; | Thienothiophene dicarbaldehyde (5 g, 25.48 mmol) is dissolved in 250 mL of dry diethylether and dry tetrahydrofuran (THF) and then, cooled down to -78 C. Then, 42.12 mL of diisopropylamine (a 2.0 M hexane solution) is slowly added thereto in a dropwise fashion, and 2,3-dibromopyridine (13.3 g, 56.16 mmol) is added thereto. The mixture is slowly heated and stirred at room temperature (24 C.) for 12 hours. Subsequently, 100 mL of an ammonium chloride-saturated solution is added thereto, and an extract is obtained by using chloroform and several times washed with water. The obtained extract is dried with magnesium sulfate and then, filtered, and the chloroform solvent is removed to obtain a compound 2a. (a yield of 75%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In water; N,N-dimethyl-formamide; at 60℃;Inert atmosphere; | A mixture of compound 1 (237 mg, 1 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (154 mg, 1 mmol), aq. K3PO4 (3 mL, 1 M, 3 mmol) and Pd(dppf)Cl2 (73 mg, 0.1 mmol) in DMF (10 mL) was stirred at 60 C under N2 for 3 h. The reaction mixture was diluted with H2O and extracted with EA. The organic layer was washed with H2O, brine, dried over Na2SO4. After concentrated, the residue was purified by silica gel column chromatography (PE : EA = 30:1) to give the product of compound 2 (170 mg, yield: 92 %). 1H-NMR (CDCl3, 400 MHz) d 8.70 (s, 1H), 8.45 (d, J = 7.2Hz, 1H), 7.41 (d, J = 7.2Hz, 1H), 6.98 (q, J = 6.8Hz, 1H), 5.94 (d, J = 17.6Hz, 1H), 5.60 (d, J = 11.2Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In water; N,N-dimethyl-formamide; at 60℃; for 4h; | A mixture of compound 1 (118 mg, 0.5 mmol), (1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid (130 mg, 0.5 mmol), aq. K3PO4 (1 M, 1.5 mmol) and Pd(dppf)Cl2 (37 mg, 0.05 mmol) in DMF (5 mL) was stirred at 60 C for 4 h. The reaction mixture was diluted with H2O and extracted with EA. The organic layer was washed with H2O, brine, dried over Na2SO4. After concentrated, the residue was purified by prep-TLC (PE : EA = 5:1) to give the product of compound 2 (100 mg, yield: 54 %). 1H NMR (CDCl3, 400 MHz) delta 8.77 (s, 1H), 8.58 (d, J = 4.4Hz, 1H), 8.30 (d, J = 8.4Hz, 1H), 7.60 (d, J = 7.6Hz, 1H), 7.25~7.41 (m, 3H), 6.58 (s, 1H), 1.33 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.4% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 168h;Inert atmosphere; Reflux; | Example 26 Synthesis of 1,1',1"-trihexyl-[4,3':4',4"-terpyridine]-1,1',1"-triium tris(tetrafluoroborate) A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.32 g, 11.3 mmol), <strong>[13534-90-2]3,4-dibromopyridine</strong> (1.22 g, 5.0 mmol), Pd(PPh3)4 (0.30 g, 0.25 mmol, 5 mol %) and K2CO3 (1.56 g, 11.3 mmol) in degassed EtOH (25 mL) and PhMe (25 mL) under N2 was heated at reflux for 7 days, cooled, diluted with water (50 mL) and extracted with DCM (4*75 mL). The organic portions were dried with anhydrous sodium sulfate and the solvent removed in vacuo to yield a red oil. The residue was chromatographed on silica, eluting with 5% MeOH in ethyl acetate to yield 4,3':4',4"-terpyridine as a cream powder (0.66 g, 56.4%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: [00286] A mixture of 5-amino-3-(3-hydroxy-3-methyl-butyl)-1-methyl-benzimidazol-2-one (Intermediate A1 , 20 mg, 0.08 mmol), Xantphos (12 mg, 0.02 mmol), 4-bromo-3-chloro-2- fluoropyridine (24 mg, 0.1 1 mmol), tris(dibenzylideneacetone)dipalladium(0) (2.3 mg, 0.004 mmol), and 4-bromo-3-chloro-2-fluoropyridine (24.00 mg, 0.1141 mmol) in NMP (0.9 mL), and toluene (0.9 mL) was degassed and heated in the microwave under a nitrogen atmosphere to 140 C for 1 hour, then purified by SCX-2 column, eluting with DCM, methanol then methanolic ammonia. Compound eluted in the non-basic fractions, and was purified further by reverse phase chromatography (Biotage Snap Ultra C18 12g, 40-80% methanol in water, 0.1 % formic acid modifier) to give 5-[(3-chloro-2-fluoro-4-pyridyl)amino]-3-(3-hydroxy-3-methyl-butyl)-1- methyl-benzimidazol-2-one (20 mg, 66%, 0.053 mmol) (2597) [00287] 1 H NMR (500 MHz, Chloroform-d) delta 7.73 (d, J=6.0 Hz, 1 H), 7.02 (app s, 2H), 6.94 (s, 1 H), 6.64 (s, 1 H, NH), 6.59 (d, J=6 Hz, 1 H), 4.09 - 4.02 (m, 2H), 3.46 (s, 3H), 2.18 (v br, 1 H, OH), 1.92 - 1.86 (m, 2H), 1.31 (s, 6H). LCMS (Method X4) Rt 2.57min; m/z 379.1336 expected 379.1337 for C18H21CIFN4O2 [M+H]+. |
Tags: 13534-90-2 synthesis path| 13534-90-2 SDS| 13534-90-2 COA| 13534-90-2 purity| 13534-90-2 application| 13534-90-2 NMR| 13534-90-2 COA| 13534-90-2 structure
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