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[ CAS No. 28948-58-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 28948-58-5
Chemical Structure| 28948-58-5
Chemical Structure| 28948-58-5
Structure of 28948-58-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 28948-58-5 ]

CAS No. :28948-58-5 MDL No. :MFCD04973300
Formula : C7H4ClNS Boiling Point : -
Linear Structure Formula :- InChI Key :HRHLEPHFARWKKU-UHFFFAOYSA-N
M.W : 169.63 Pubchem ID :15914129
Synonyms :

Calculated chemistry of [ 28948-58-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.63
TPSA : 41.13 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.98
Log Po/w (XLOGP3) : 2.83
Log Po/w (WLOGP) : 2.95
Log Po/w (MLOGP) : 1.84
Log Po/w (SILICOS-IT) : 3.83
Consensus Log Po/w : 2.68

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.34
Solubility : 0.0774 mg/ml ; 0.000456 mol/l
Class : Soluble
Log S (Ali) : -3.35
Solubility : 0.0755 mg/ml ; 0.000445 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.58
Solubility : 0.0447 mg/ml ; 0.000264 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.29

Safety of [ 28948-58-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 28948-58-5 ]

* 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 [ 28948-58-5 ]

[ 28948-58-5 ] Synthesis Path-Downstream   1~74

  • 2
  • [ 28948-58-5 ]
  • [ 2622-05-1 ]
  • [ 87651-08-9 ]
  • 3
  • [ 28948-58-5 ]
  • [ 85517-71-1 ]
  • [ 88255-40-7 ]
  • 4
  • [ 28948-58-5 ]
  • [ 104587-44-2 ]
  • 5
  • [ 738544-01-9 ]
  • [ 28948-58-5 ]
  • 6
  • [ 28981-13-7 ]
  • [ 28948-58-5 ]
YieldReaction ConditionsOperation in experiment
In phosphorous oxy chloride; dichloromethane; C. 7-Chloro-thieno[2,3-c]pyridine. 6H-Thieno[2,3-c]pyridin-7-one (2.3 g, 15.22 mmol) is dissolved in 50 mL of phosphorous oxy chloride. The solution is heated to 100 C. After 4 hours, the solution is concentrated. The residue is dissolved in CH2 Cl2. The resulting solution is washed with water and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluding with a gradient of 40% CH2 Cl2 /hexanes to 60% CH2 Cl2 /hexanes. The title compound (2.0 g, 12.2 mmol) is obtained as a white solid. 1 H NMR (CDCl3, 300 MHz) delta8.26 (d, 1H), 7.76 (d, 1H), 7.62 (d, 1H), 7.41 (d, 1H). EI MS, [M]+ =169, 171, Cl pattern.
  • 8
  • [ 28948-58-5 ]
  • [ 106261-06-7 ]
  • 10
  • [ 28948-58-5 ]
  • [ 87651-10-3 ]
  • 11
  • [ 28948-58-5 ]
  • [ 87651-14-7 ]
  • 12
  • [ 28948-58-5 ]
  • [ 87651-09-0 ]
  • 13
  • [ 28948-58-5 ]
  • 5-Allyl-6-methyl-4,5-dihydrothieno<2,3-c>pyridinium-perchlorat [ No CAS ]
  • 14
  • [ 28948-58-5 ]
  • [ 104587-06-6 ]
  • 15
  • [ 28948-58-5 ]
  • 7-Oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carbonyl chloride [ No CAS ]
  • 16
  • [ 28948-58-5 ]
  • [ 104604-78-6 ]
  • 17
  • [ 28948-58-5 ]
  • [ 104587-49-7 ]
  • 18
  • [ 28948-58-5 ]
  • [ 104586-97-2 ]
  • 19
  • [ 28948-58-5 ]
  • [ 130888-44-7 ]
  • 20
  • [ 28948-58-5 ]
  • [ 104604-87-7 ]
  • 21
  • [ 28948-58-5 ]
  • [ 104587-13-5 ]
  • 22
  • [ 104587-43-1 ]
  • [ 28948-58-5 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In 1,4-dioxane; water; toluene; (adb) 671.5 g of thieno[2,3-c]pyridine 6-oxide hydrochloride were suspended in 4000 ml of dioxane under argon and 655 ml of phosphorus oxychloride are added. The mixture was heated on an oil-bath until the exothermic reaction set in. After the exothermic reaction faded away, the mixture was heated to reflux for an additional 10 minutes. The mixture was concentrated in vacuo and the residue was taken up in 2000 ml of toluene. The solution was then treated with 300 ml of water while cooling slowly. The mixture was neutralized by the portionwise addition of sodium carbonate. The organic phase was separated and the aqueous phase was extracted with 1000 ml of toluene. After washing with water, the combined organic solutions were dried over sodium sulfate, filtered and evaporated, whereby crude 7-chloro-thieno[2,3-c]pyridine was obtained as a brown oil.
  • 23
  • [ 28948-58-5 ]
  • sodium hydrosulfide monohydrate [ No CAS ]
  • [ 104587-44-2 ]
YieldReaction ConditionsOperation in experiment
In N-methyl-acetamide; ice-water; (adc) 4.85 g of <strong>[28948-58-5]7-chloro-thieno[2,3-c]pyridine</strong> was dissolved in 15 ml of dimethylformamide and 3.18 g of sodium hydrogen sulfide monohydrate were added under argon. The mixture was heated to 110-115 for one hour, an additional 1.06 g of sodium hydrogen sulfide monohydrate were added and the mixture was held at the temperature indicated above for an additional hour. The mixture was poured on to 150 ml of ice-water and acidified with 1N aqueous hydrochloric acid solution. After stirring at 2 for a short time, the yellowish crystals were removed by filtration. After recrystallization from a toluene/ethyl acetate mixture, there was obtained pure thieno[2,3-c]pyridine-7(6H)-thione, m.p. 187-189.
  • 24
  • [ 28948-58-5 ]
  • [ 201230-82-2 ]
  • [ 1078167-97-1 ]
  • 25
  • [ 109-01-3 ]
  • [ 28948-58-5 ]
  • 7-(4-methylpiperazin-1-yl)thieno[2,3-c]pyridine [ No CAS ]
  • 26
  • [ 4430-75-5 ]
  • [ 28948-58-5 ]
  • 7-octahydropyrido[1,2-a]pyrazin-2-yl-thieno[2,3-c]pyridine [ No CAS ]
  • 27
  • [ 28948-58-5 ]
  • [ 93643-24-4 ]
  • 7-((8aS)-hexahydropyrrolo[1,2-a]pyrazin-2-yl)thieno[2,3-c]pyridine [ No CAS ]
  • 28
  • [ 28948-58-5 ]
  • [ 96193-27-0 ]
  • 7-((8aR)-hexahydropyrrolo[1,2-a]pyrazin-2-yl)thieno[2,3-c]pyridine [ No CAS ]
  • 29
  • [ 28948-58-5 ]
  • [ 5961-59-1 ]
  • [ 1173825-66-5 ]
  • 30
  • [ 28948-58-5 ]
  • [ 1402599-42-1 ]
  • [ 1402598-77-9 ]
YieldReaction ConditionsOperation in experiment
A 25 mL round-bottomed flask was charged with 7- chlorothieno[2,3-c]pyridine (0.25 g, 1.5 mmol, Ellanova, Hamden, CT) and tetrahydrofuran (7.4 mL). The solution was cooled to -78 C, n-butyllithium (0.65 mL of a 2.5 M solution with toluene, 1.6 mmol, Sigma- Aldrich, St. Louis, MO) was added, and then the reaction mixture was stirred for 15 min. After that time, a solution of N-(phenylmethylidene)-3,4-dihydro-2H-l,5-benzodioxepine-7- sulfonamide (Intermediate I) (0.51 g, 1.6 mmol) and tetrahydrofuran (7.4 mL) was added. After stirring for 10 min, methanol (2.0 mL) was added, the reaction mixture was removed from the cooling bath and allowed to warm to room temperature, silica gel (3.5 g) was added, and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (35 g of silica gel, gradient elution, 3:1 to 2: 1 hexane-ethyl acetate). The isolated material was dissolved with dichloromethane (20 mL), silica gel (3.5 g) was added, and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (35 g of silica gel, 49:1 dichloromethane-diethyl ether) to give N-((7-chlorothieno[2,3-c]pyridin-2-yl)(phenyl)methyl)-3,4-dihydro- 2H-l,5-benzodioxepine-7-sulfonamide (0.42 g) as a colorless solid.1H NMR (400 MHz, DMSO-d6) delta 9.11 (br. s., 1 H), 8.26 (d, J= 5.3 Hz, 1 H), 7.75 (d, J = 5.5 Hz, 1 H), 7.36 - 7.21 (m, 6 H), 7.19 (d, J = 1.0 Hz, 1 H), 7.13 (d, J= 2.3 Hz, 1 H), 6.87 (d, J= 8.4 Hz, 1 H), 5.98 (br. s., 1 H), 4.05 (t, J= 5.7 Hz, 2 H), 4.01 - 3.90 (m, 2 H), 2.11 - 1.98 (m, 2 H). m/z (ESI, +ve ion) 486.8 (M+H)+. GK-GKRP ICso (Binding) = 1.1 muMu.
  • 31
  • [ 28948-58-5 ]
  • [ 1402599-08-9 ]
  • 1,1,1-trifluoro-2-(2-thieno[2,3-c]pyridin-7-yl-4-pyridinyl)-2-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.25 g With bis(eta3-allyl-mu-chloropalladium(II)); cesium fluoride; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; water; at 80 - 100℃; for 37h;Inert atmosphere; A stirring mixture of 2-(2-chloro-4-pyridinyl)- 1,1,1 -trifluoro-2-propanol (1.0 g, 4.4 mol, Intermediate XI), <strong>[28948-58-5]7-chlorothieno[2,3-c]pyridine</strong> (1.1 g, 6.7 mol, Ellanova, Inc., Hamden, CT), 1,4-dioxane (14 mL), water (3.5 mL), allylpalladium(II) chloride dimer (0.16 g, 0.44 mmol), 9,9-dimethyl-4,5- bisdiphenylphosphino)xanthene (0.51 g, 0.89 mmol), and cesium fluoride (2.0 g, 13 mol) was heated at 80 C under a nitrogen atmosphere. After 24 h, the reaction mixture was heated at 100 C. After an additional 13h, the reaction mixture was allowed to cool to room temperature and concentrated under a vacuum. The residue was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate, the layers were separated, the organic material was washed sequentially with saturated aqueous sodium bicarbonate and brine. The combined extracts were dried (sodium sulfate), filtered, and concentrated under a vacuum. The residue was dissolved with dichloromethane, silica gel (10 g) was added to the solution, and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (4: 1 hexane-ethyl acetate) to give l,l,l-trifluoro-2-(2-thieno[2,3-c]pyridin-7-yl-4-pyridinyl)-2- propanol (0.25 g, Intermediate Y6) as an off-white solid (racemic mixture)
  • 32
  • [ 28948-58-5 ]
  • di-tert-butyl (6-((E)-(((S)-tert-butylsulfinyl)imino)methyl)-5-chloro-2-pyridinyl)imidodicarbonate [ No CAS ]
  • tert-butyl (6-((((R)-tert-butylsulfinyl)amino)(7-chlorothieno[2,3-c]pyridin-2-yl)methyl)-5-chloro-2-pyridinyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.27 g To a stirring solution of <strong>[28948-58-5]7-chlorothieno[2,3-c]pyridine</strong> (1.06 g, 6.25 mmol, see Examples 104 and 105, Step 3) in THF (10 mL) at -72 C under nitrogen was added n-butyllithium, 2.5 M solution in hexanes (2.75 mL, 6.87 mmol) (on the side of round bottom flask) at a rate that did not exceed an internal temp of -60 C. To the reaction, after 5 min, was added a solution of di-tert-butyl (6-((E)-(((R)-tert-butylsulfinyl)imino)methyl)-5-chloro-2- pyridinyl)imidodicarbonate (2.87 g, 6.25 mmol, Intermediate AA4) in THF (1 mL). After 20 min the cooling bath was removed, the reaction warmed to -30 C, then quenched with saturated NH4C1 (4 mL). The reaction was then partitioned between EtOAc (60 mL) and saturated NH4CI (30 mL). The organic was the dried over MgSC^, concentrated under reduced pressure, then purified by silica gel chromatography (120 g) eluting products with 10 to 50% gradient of EtO Ac/Hex to afford tert-butyl (6-((((R)-tert-butylsulfmyl)amino)(7- chlorothieno[2,3-c]pyridin-2-yl)methyl)-5-chloro-2-pyridinyl)carbamate (1.27 g) as white solid (mixture of 2 diastereomers).
  • 33
  • [ 1124-65-8 ]
  • [ 28948-58-5 ]
  • 34
  • [ 28424-61-5 ]
  • [ 28948-58-5 ]
  • 35
  • thieno[2,3-c]pyridin-7-ol [ No CAS ]
  • [ 28948-58-5 ]
YieldReaction ConditionsOperation in experiment
14 g With trichlorophosphate; for 2.5h;Reflux; A suspension of thieno[2,3-c]pyridin-7-ol (22 g, 146 mmol) in phosphoryl trichloride (100 mL) was stirred at reflux for 2.5hr. The reaction mixture was cooled to 20 C, poured into ice water (500 mL), stirred for 30 min, then extracted into CH2C12 (3 x 100 mL). The organic layer was dried over Na2S04, filtered, then concentrated under reduced pressure to afford 7- chlorothieno[2,3-c]pyridine as brown solid (14 g).
  • 36
  • [ 28948-58-5 ]
  • (S)-N-((R)-(2-chlorophenyl)(7-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)-2-pyridinyl)thieno[2,3-c]pyridin-2-yl)methyl)-2-methyl-2-propanesulfinamide [ No CAS ]
  • 37
  • [ 28948-58-5 ]
  • N-((R)-(3-chloro-2-pyridinyl)(7-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)-2-pyridinyl)thieno[2,3-c]pyridin-2-yl)methyl)-2-methyl-2-propanesulfinamide [ No CAS ]
  • 38
  • [ 28948-58-5 ]
  • tert-butyl (6-(amino(7-chlorothieno[2,3-c]pyridin-2-yl)methyl)-5-chloro-2-pyridinyl)carbamate [ No CAS ]
  • 39
  • [ 28948-58-5 ]
  • tert-butyl (5-chloro-6-((7 chlorothieno[2,3-c]pyridin-2-yl)(cyclopropanesulfonamido)methyl)pyridin-2-yl)carbamate [ No CAS ]
  • 40
  • [ 28948-58-5 ]
  • tert-butyl (5-chloro-6-(((cyclopropylsulfonyl)amino)(7-(4-(1-hydroxy-1-methylethyl)-2-pyridinyl)thieno[2,3-c]pyridin-2-yl)methyl)-2-pyridinyl)carbamate [ No CAS ]
  • 41
  • [ 28948-58-5 ]
  • N-((6-amino-3-chloro-2-pyridinyl)(7-(4-(1-hydroxy-1-methylethyl)-2-pyridinyl)thieno[2,3-c]pyridin-2-yl)methyl)cyclopropanesulfonamide [ No CAS ]
  • 42
  • [ 28948-58-5 ]
  • (S)-N-((3,6-dichloro-2-pyridinyl)(7-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)-2-pyridinyl)thieno[2,3-c]pyridin-3-yl)methyl)-2-methyl-2-propanesulfinamide [ No CAS ]
  • 43
  • [ 28948-58-5 ]
  • 2-(2-(3-(amino(3,6-dichloro-2-pyridinyl)methyl)thieno[2,3-c]pyridin-7-yl)-4-pyridinyl)-1,1,1-trifluoro-2-propanol [ No CAS ]
  • 44
  • [ 28948-58-5 ]
  • tert-butyl ((3,6-dichloro-2-pyridinyl)(7-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)-2-pyridinyl)thieno[2,3-c]pyridin-3-yl)methyl)carbamate [ No CAS ]
  • 45
  • [ 28948-58-5 ]
  • tert-butyl ((3-chloro-6-((4-methoxybenzyl)amino)-2-pyridinyl)(7-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)-2-pyridinyl)thieno[2,3-c]pyridin-3-yl)methyl)carbamate [ No CAS ]
  • 46
  • [ 28948-58-5 ]
  • 2-(2-(3-(amino(6-amino-3-chloro-2-pyridinyl)methyl)thieno[2,3-c]pyridin-7-yl)-4-pyridinyl)-1,1,1-trifluoro-2-propanol [ No CAS ]
  • 47
  • [ 28948-58-5 ]
  • N-((6-amino-3-chloro-2-pyridinyl)(7-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)-2-pyridinyl)thieno[2,3-c]pyridin-2-yl)methyl)cyclopropanesulfonamide [ No CAS ]
  • 48
  • [ 28948-58-5 ]
  • [ 1609259-88-2 ]
  • 2-methyl-1-[2-methyl-4-(thieno[2,3-c]pyridin-7-yloxy)phenyl]-1H-imidazo[4,5-c]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With caesium carbonate; In dimethyl sulfoxide; at 130℃; for 16h; Dimethyl sulfoxide (0.9 mL) was added to a mixture of <strong>[28948-58-5]7-chlorothieno[2,3-c]pyridine</strong> (36.8 mg, 0.217 mmol), C35 (51.9 mg, 0.217 mmol), and cesium carbonate(142 mg, 0.436 mmol), and the reaction mixture was heated at 130 00 for 16 hours.Ethyl acetate (5 mL) was added, and the mixture was filtered through silica gel (1 g),eluting with additional ethyl acetate (10 mL). The filtrate was concentrated in vacuo;purification via reversed phase HPLC (Column: Waters XBridge, 5 pm; Mobile phase A: 0.03% ammonium hydroxide in water (vlv); Mobile phase B: 0.03% ammoniumhydroxide in acetonitrile (vlv); Gradient: 35% to 100% B) provided the product. Yield:21.5 mg, 57.7 pmol, 27%. LCMS m/z 373.0 [M+H]. Retention time: 2.30 minutes(Column: Waters Atlantis dCl8, 4.6 x 50 mm, 5 pm; Mobile phase A:0.05% trifluoroacetic acid in water (v/v); Mobile phase B: 0.05% trifluoroacetic acid in acetonitrile (v/v); Gradient: 5.0% to 95% B, linear over 4.0 minutes; Flow rate: 1.5 mL/minute).
  • 49
  • [ 28948-58-5 ]
  • 3-methoxy-4-(3-methylpyrazin-2-yl)phenol [ No CAS ]
  • 7-[3-methoxy-4-(3-methylpyrazin-2-yl)phenoxy]thieno[2,3-c]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 120℃; for 3h;Inert atmosphere; 7-Chlorothieno[2,3-c]pyridine (350 mg, 2.06 mmol), 1,1 ?-binaphthalene-2,2?-diylbis(diphenylphosphane) (BINAP, 261 mg, 0.419 mmol), cesium carbonate (1.68 g,5.16 mmol), and palladium(ll) acetate (47 mg, 0.21 mmol) were added to a solution ofC41 (371 mg, 1.72 mmol) in 1 ,4-dioxane (5 mL). The reaction mixture was degassedwith nitrogen for 5 minutes, then heated at 120 00 for 3 hours, whereupon it was filtered.The filtrate was concentrated in vacuo, and the residue was purified by silica gel chromatography to afford the product as a white solid. Yield: 270 mg, 0.77 mmol, 45%. LCMS m/z350.2 [M+H]. 1H NMR (400 MHz, CD3OD) oe 8.49 (5, 2H), 8.00 (d, J=1.6 Hz, 1H), 7.98 (d, J=1.9 Hz, 1H), 7.61 (d, J=5.5 Hz, 1H), 7.54 (d, J=5.4 Hz, 1H), 7.36 (d,J=8.3 Hz, 1H), 7.06 (d, J=2.1 Hz, 1H), 6.94 (dd, J=8.2, 2.1 Hz, 1H), 3.80 (5, 3H), 2.47 (5,3H).
  • 50
  • [ 28948-58-5 ]
  • [ 102127-34-4 ]
  • 7-(4-bromo-3-methoxyphenoxy)thieno[2,3-c]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In dimethyl sulfoxide; 15. Reaction of <strong>[102127-34-4]4-bromo-3-methoxyphenol</strong> with 7-chlorothieno[2,3-c]pyridine and cesium carbonate in dimethyl sulfoxide at elevated temperature provided 7-(4-bromo-3- methoxyphenoxy)thieno[2, 3-c]pyridine
  • 51
  • [ 28948-58-5 ]
  • [ 1609259-73-5 ]
  • 7-[4-(3,5-dimethylpyridazin-4-yl)-3-methylphenoxy]thieno[2,3-c]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With caesium carbonate; In dimethyl sulfoxide; at 140℃; for 3h; A mixture of C52 (21.5 mg, 0.100 mmol), <strong>[28948-58-5]7-chlorothieno[2,3-c]pyridine</strong> (18.5 mg, 0.109 mmol), and cesium carbonate (141 mg, 0.433 mmol) in dimethyl sulfoxide (1 mL) was heated at 140 00 for 3 hours, filtered through a syringe filter disk, and subjected to reversed phase HPLC (Column: Waters Sunfire 018, 5 pm; Mobile phase A:0.05% trifluoroacetic acid in water (vlv); Mobile phase B: 0.05% trifluoroacetic acid inacetonitrile (vlv); Gradient: 25% to 100% B) to afford the product. Yield: 27.5 mg, 79.2pmol, 79%. LCMS m/z 348.2 [M+H]. 1H NMR (600 MHz, DMSO-d6) oe 9.15 (5, 1H), 8.18(d, J=5.3 Hz, 1H), 8.05 (d, J=5.5 Hz, 1H), 7.66 (d, J=5.5 Hz, 1H), 7.63 (d, J=5.4 Hz, 1H),7.33 (brd, J=2.2 Hz, 1H), 7.25 (brdd, J=8.2, 2.5 Hz, 1H), 7.18 (d, J=8.2 Hz, 1H), 2.34(5, 3H), 2.06 (5, 3H), 1.96 (5, 3H).
  • 52
  • [ 28948-58-5 ]
  • [ 1609259-39-3 ]
  • 1,5-dimethyl-6-[2-methyl-4-(thieno[2,3-c]pyridin-7-yloxy)phenyl]pyrazin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 120℃; for 3h; A mixture of C26 (91.8 mg, 0.295 mmol), <strong>[28948-58-5]7-chlorothieno[2,3-c]pyridine</strong> (50 mg,0.29 mmol), palladium(ll) acetate (6.50 mg, 29.0 pmol), 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (34.1 mg, 59.0 pmol) and cesium carbonate (288 mg, 0.884 mmol) in1 ,4-dioxane (2 mL) was heated at 120 00 for 3 hours, whereupon it was allowed to cool to room temperature and filtered. After removal of volatiles in vacuo, the residue was purified by chromatography on silica gel (Gradient: 0% to 25% [80:20:1 dichloromethane I methanol I concentrated ammonium hydroxide] in dichloromethane). The product was obtained as a solid. Yield: 38 mg, 0.10 mmol, 34%. LCMS m/z 364.1 [M+H]. 1H NMR(400 MHz, ODd3) oe 8.19 (5, 1H), 8.06 (d, J=5.6 Hz, 1H), 7.76 (d, J=5.3 Hz, 1H), 7.49 (d, J=5.5 Hz, 1H), 7.43 (d, J=5.4 Hz, 1H), 7.26-7.31 (m, 2H, assumed; partially obscured by solvent peak), 7.17 (d, J=8.2 Hz, 1H), 3.24 (5, 3H), 2.13 (5, 3H), 2.05 (5, 3H).
  • 53
  • [ 28948-58-5 ]
  • [ 1609259-55-3 ]
  • 7-[4-(4,6-dimethylpyrimidin-5-yl)-3-methylphenoxy]thieno[2,3-c]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 120℃; for 3h; A mixture of <strong>[28948-58-5]7-chlorothieno[2,3-c]pyridine</strong> (100 mg, 0.59 mmol), C28 (126 mg, 0.590 mmol), palladium(ll) acetate (13.2 mg, 58.8 pmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (68.3 mg, 0.118 mmol), and cesium carbonate (769 mg, 2.36mmol) in 1,4-dioxane (3 mL) was heated at 120 00 for 3 hours. After the reaction mixture had been cooled to room temperature and filtered through a syringe filter using ethyl acetate, the filtrate was concentrated in vacuo and subjected to silica gel chromatography (Gradient: 0% to 50% [80:20:1 dichloromethane I methanol I concentrated ammonium hydroxide] in dichloromethane). The product was isolated as asolid. Yield: 140 mg, 0.403 mmol, 68%. LCMS m/z348.1 [M+H]. 1H NMR (400 MHz,ODd3) oe 8.99 (5, 1H), 8.09 (d, J=5.6 Hz, 1H), 7.76 (d, J=5.4 Hz, 1H), 7.49 (d, J=5.6 Hz,1 H), 7.44 (d, J=5.4 Hz, 1 H), 7.29 (br d, J=2.4 Hz, 1 H), 7.24 (br dd, J=8.3, 2.4 Hz, 1 H),7.09 (d, J=8.2 Hz, 1H), 2.29 (5, 6H), 2.04 (5, 3H).
  • 54
  • [ 28948-58-5 ]
  • [ 1066-45-1 ]
  • 7-chloro-2-(trimethylstannyl)thieno[2,3-c]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a cooled (-78C) solution of <strong>[28948-58-5]7-chlorothieno[2,3-c]pyridine</strong> (250 mg, 1.47mmol) in THF (20 mL) was addedn-BuLi(2.5 M in hexanes, 0.7 mL, 1.77mmol)dropwiseover 10 minutes. On complete addition the mixture was allowed to stir for 20 minutes at-78C before the addition of a solution oftrimethylstannylchloride (352 mg, 1.76mmol) in THF (1 mL). The mixture was allowed to warm to room temperature and quenched by the addition of saturated ammonium chloride solution (50 mL). Diethyl ether (50 mL) was added and the layers separated. The organic phase was washed with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered and evaporated to afford the crude title compound as a yellow solid, which was carried to the next step without further purification. H NMR (300 MHz, CDCl3):d8.20 (d,J= 5.5 Hz, 1H), 7.56 (d,J= 5.4 Hz, 1H), 7.43 (s, 1H), 0.45 - 0.44 (m, 9H).
  • 55
  • [ 28948-58-5 ]
  • C17H12Cl2N2OS [ No CAS ]
  • 56
  • [ 28948-58-5 ]
  • 7-chloro-2-(2,6-dichlorophenyl)thieno[2,3-c]pyridine [ No CAS ]
  • 57
  • [ 28948-58-5 ]
  • [ 29512-82-1 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate; at 26℃; for 16h; 7-Chlorothieno[2,3-c]pyridine (300 mg, 1.06 mmol) in NH2NH2.H2O (5 mL) was stirred at 26 C. for 16 h. The mixture was extracted with CH2Cl2 (20*3 mL). The solvent was concentrated under reduced pressure the give the desired compound, used directly for the next step without further purification.
  • 58
  • [ 28948-58-5 ]
  • 1-(thieno[2,3-c]pyridin-7-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid [ No CAS ]
  • 59
  • [ 28948-58-5 ]
  • N-(5-cyano-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)-1-(thieno[2,3-c]pyridin-7-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide [ No CAS ]
  • 60
  • [ 28948-58-5 ]
  • ethyl 1-(thieno[2,3-c]pyridin-7-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate [ No CAS ]
  • 61
  • [ 28948-58-5 ]
  • [ 320-49-0 ]
  • C14H7BrF3NOS [ No CAS ]
  • 64
  • [ 28948-58-5 ]
  • C20H19BF3NO3S [ No CAS ]
  • 65
  • [ 28948-58-5 ]
  • 7-(3-methyl-4-(6-methylimidazo[1,2-a]pyrazin-5-yl)phenoxy)thieno[2,3-c]pyridine [ No CAS ]
  • 66
  • [ 28948-58-5 ]
  • 7-(4-(imidazo[1,2-a]pyridin-5-yl)-3-(trifluoromethyl)phenoxy)thieno[2,3-c]pyridine [ No CAS ]
  • 67
  • [ 28948-58-5 ]
  • 1,5-dimethyl-6-(2-methyl-4-(thieno[2,3-c]pyridin-7-yloxy)-phenyl)pyrimidine-2,4(1H,3H)-dione [ No CAS ]
  • 68
  • [ 28948-58-5 ]
  • 4-fluoro-6-methylthieno[2,3-c]pyridin-7(6H)-one [ No CAS ]
  • 69
  • [ 28948-58-5 ]
  • 6-methylthieno[2,3-c]pyridin-7(6H)-one [ No CAS ]
  • 70
  • [ 28948-58-5 ]
  • [ 28981-13-7 ]
  • 71
  • [ 28948-58-5 ]
  • [ 124-41-4 ]
  • C8H7NOS [ No CAS ]
  • 72
  • [ 28948-58-5 ]
  • C20H20ClN3O2S [ No CAS ]
  • 73
  • [ 28948-58-5 ]
  • C13H14N2O2S [ No CAS ]
  • 74
  • [ 28948-58-5 ]
  • [ 2971-79-1 ]
  • C14H16N2O2S [ No CAS ]
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