Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 25797-03-9 | MDL No. : | MFCD09908215 |
Formula : | C13H10N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MHTVGGZESFVQIQ-UHFFFAOYSA-N |
M.W : | 194.23 | Pubchem ID : | 11310078 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 15 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 61.53 |
TPSA : | 28.68 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.55 cm/s |
Log Po/w (iLOGP) : | 1.88 |
Log Po/w (XLOGP3) : | 2.73 |
Log Po/w (WLOGP) : | 3.23 |
Log Po/w (MLOGP) : | 2.14 |
Log Po/w (SILICOS-IT) : | 3.6 |
Consensus Log Po/w : | 2.72 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.44 |
Solubility : | 0.0708 mg/ml ; 0.000365 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.99 |
Solubility : | 0.2 mg/ml ; 0.00103 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.43 |
Solubility : | 0.00072 mg/ml ; 0.00000371 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.91 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
80% | Stage #1: With pyridine N-oxide; phosphorus trichloride In chloroform at 80℃; for 7 h; Stage #2: With sodium hydrogencarbonate In chloroform; water at 0℃; for 0.5 h; |
Phosphorus trichloride (0.02 niL, d 1.57, 0.22 mmol) was added dropwise to a stirred solution of the pyridine N-oxide (12 mg, 0.038 mmol) in CHCl3 (1 mL). The reaction mixture was heated to 80 °C for 7 h. Ice was added to the reaction mixture and then15 neutralized to pH 10 using saturated aqueous NaHCO3 solution. After stirring for 30 min, the mixture was extracted using CHCl3 (3 x 15 mL). The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified using chromatography eluting with 100percent EtOAc to 10percent MeOH/EtOAc to give the product as a white solid (6 mg, 0.03 mmol, 80percent). mp: 250-252 °C. ER (neat, cm"1):20 3439, 1642. 1H NMR (400 MHz, MeOD) δ 7.23 (IH, s), 6.58 (IH, d, J - 5.7 Hz), 6.29 (2H, d, J = 7.7 Hz), 5.93 (2H, t, J= 7.5 Hz), 5.89 (IH, d, J= 5.9 Hz), 5.82 (IH, t, J= 7.3 Hz), 5.45 (IH, s). 13C NMR (100 MHz, MeOD) δ 143.5, 142.8, 141.9, 140.5, 133.2, 130.3, 129.5, 127.9, 126.8, 108.1, 99.1, 99.1. HRMS (ESI): calc'd for Ci3H10N2 ([M]+) 194.0844. Found: 194.0852 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; copper(I) thiophene-2-carboxylate; 1,3-bis-(diphenylphosphino)propane; triethylamine In tetrahydrofuran at 100℃; for 15 h; Inert atmosphere; Schlenk technique; Sealed tube | General procedure: Pyridine-2-thione (0.1 mmol), CuTC (0.1 mmol), CuI (0.05mol),Pd(PPh3)2Cl2 (0.005mol), dppp (0.02 mmol), phenyl-acetylene (0.3 mmol), Et3N (3 mL) and THF (3 mL) were added to a 35 mL sealed tube and stirred at 100 °C for 15 h under argon atmosphere. The reaction mixture was then cooled to room temperature and then diluted with EtOAc (25 mL) and filtered through celite with EtOAc (50 mL). The crude products were purified by flash column chromatography on a silica gel column with petroleum ether/ethylacetate as the eluent to afford the corresponding purified products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; di(1-adamantyl)benzylphosphonium hydrobromide In dimethyl sulfoxide at 100℃; for 1 h; Schlenk technique; Inert atmosphere Stage #2: With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 100℃; for 0.25 h; Schlenk technique; Inert atmosphere |
General procedure: 3-Amino-2-bromopyridine (1a) (87 mg, 0.5 mmol) or2-bromoaniline (1b) (172 mg, 1.00 mmol), Pd(PPh3)2Cl2(9.0 mg, 13 mmol or 17.5 mg, 25.0 mmol), and(1-Ad)2PBn·HBr (12 mg, 25 mmol or 23.6 mg, 50.0 mmol)were placed into a dry screw-cap Schlenk tube with amagnetic stirring bar, and the vessel was evacuated. Afterflushing the vessel with nitrogen, dry DMSO (1.0 or 1.5 ml),the corresponding alkyne 2a–j (0.6 mmol or 1.2 mmol),and DBU (225 mg, 1.50 mmol or 457 mg, 3.00 mmol)were added. The reaction mixture was stirred at 100°Cunder nitrogen for 1 h until the bromide was completelyconsumed (monitored by TLC). After cooling to roomtemperature, KOt-Bu (253 mg, 2.25 mmol or 281 mg,2.50 mmol) and DMSO (0.50 or 1.00 ml) were added to thereaction mixture, and the mixture was stirred at 100°Cunder nitrogen for 0.25 h. After cooling to roomtemperature, deionized water or brine (20 ml) was added tothe mixture. The aqueous layer was extracted several timeswith EtOAc or CH2Cl2. The combined organic phases weredried over anhydrous Na2SO4 and after filtration, thesolvents were removed under reduced pressure. The residuewas purified by flash chromatography on silica gel to givethe analytically pure products 3a–j. 2-Phenyl-1H-pyrrolo[3,2-b]pyridine (3a) was synthesizedfrom 3-amino-2-bromopyridine (1a) (87 mg, 0.5 mmol)and phenylacetylene (2a) (61 mg, 0.6 mmol), eluent forflash chromatography EtOAc–n-hexane, 3:2. Yield 53 mg(55percent), beige solid, mp 249°C. IR spectrum, ν, cm–1: 3082(w), 3053 (w), 3011 (w), 2969 (w), 2932 (w), 1603 (w),1568 (w), 1537 (w), 1481 (w), 1456 (m), 1414 (m), 1362 (m),1343 (m), 1289 (w), 1275 (m), 1227 (w), 1200 (w), 1173 (w),1157 (w), 1119 (w), 1096 (w), 1074 (w), 1053 (w), 1030 (w),988 (w), 924 (m), 910 (w), 833 (w), 810 (w), 785 (m), 766 (s),735 (m), 687 (s). 1H NMR spectrum, δ, ppm (J, Hz): 7.06(1H, s, H-3); 7.10 (1H, dd, J = 8.0, J = 4.6, H-6); 7.37–7.38(1H, m, H Ph); 7.48–7.50 (2H, m, H Ph); 7.77 (1H, d, J = 8.0, H-7); 7.92–7.93 (2H, m, H Ph); 8.31–8.32 (1H, m,H-5); 11.82 (1H, br. s, NH). 13C NMR spectrum, δ, ppm:99.2 (CH); 116.8 (CH); 118.3 (CH); 125.5 (CH); 128.4(CH); 129.2 (CH); 130.1 (C); 131.7 (C); 141.1 (C); 142.9(CH); 146.9 (C). Mass spectrum, m/z (Irel, percent): 195 (14),194 [M]+ (100), 193 (25), 192 (7), 167 (6), 166 (8), 97 (11).Found, m/z: 195.0920 [M+H]+. C13H11N2. Calculated, m/z:195.0917. |
[ 40068-81-3 ]
2-(Naphthalen-2-yl)-1H-pyrrolo[2,3-c]pyridine
Similarity: 0.91
[ 2922-07-8 ]
2-Phenyl-1H-pyrrolo[2,3-c]pyridine
Similarity: 0.91
[ 1173285-69-2 ]
6-Phenyl-5H-pyrrolo[3,2-d]pyrimidine
Similarity: 0.89
[ 40068-81-3 ]
2-(Naphthalen-2-yl)-1H-pyrrolo[2,3-c]pyridine
Similarity: 0.91
[ 2922-07-8 ]
2-Phenyl-1H-pyrrolo[2,3-c]pyridine
Similarity: 0.91
[ 1173285-69-2 ]
6-Phenyl-5H-pyrrolo[3,2-d]pyrimidine
Similarity: 0.89
[ 37388-07-1 ]
2-Phenyl-1H-pyrrolo[3,2-c]pyridine
Similarity: 0.87