Home Cart 0 Sign in  
X

[ CAS No. 97966-01-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 97966-01-3
Chemical Structure| 97966-01-3
Chemical Structure| 97966-01-3
Structure of 97966-01-3 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 97966-01-3 ]

Related Doc. of [ 97966-01-3 ]

Alternatived Products of [ 97966-01-3 ]

Product Details of [ 97966-01-3 ]

CAS No. :97966-01-3 MDL No. :MFCD09835220
Formula : C5H2Cl2IN Boiling Point : -
Linear Structure Formula :- InChI Key :XSHFSZAXOOQKQS-UHFFFAOYSA-N
M.W : 273.89 Pubchem ID :21892874
Synonyms :

Calculated chemistry of [ 97966-01-3 ]

Physicochemical Properties

Num. heavy atoms : 9
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 : 46.97
TPSA : 12.89 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) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.06
Log Po/w (XLOGP3) : 3.09
Log Po/w (WLOGP) : 2.99
Log Po/w (MLOGP) : 2.6
Log Po/w (SILICOS-IT) : 3.67
Consensus Log Po/w : 2.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.98
Solubility : 0.0288 mg/ml ; 0.000105 mol/l
Class : Soluble
Log S (Ali) : -3.03
Solubility : 0.257 mg/ml ; 0.000937 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.21
Solubility : 0.017 mg/ml ; 0.0000622 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.25

Safety of [ 97966-01-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 97966-01-3 ]

* 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 [ 97966-01-3 ]

[ 97966-01-3 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 97966-01-3 ]
  • [ 851526-80-2 ]
  • 3-(5,6-dichloro-pyridin-3-yl)-3,8-diaza-bicyclo[4.2.0]octane-8-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃;
  • 2
  • [ 97966-01-3 ]
  • [ 370881-22-4 ]
  • 3-(5,6-dichloro-pyridin-3-yl)-3,8-diaza-bicyclo[4.2.0]octane-8-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃;
  • 4
  • [ 97966-01-3 ]
  • [ 370882-99-8 ]
  • [ 370883-12-8 ]
YieldReaction ConditionsOperation in experiment
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃;
With sodium t-butanolate 94.A tert-butyl (1R,6S)-8-(5,6-dichloro-3-pyridinyl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate EXAMPLE 94A tert-butyl (1R,6S)-8-(5,6-dichloro-3-pyridinyl)-3,8-diazabicyclo[4.2.0]octane-3-carboxylate The product of Example 90C (390 mg, 1.84 mmol), Pd2(dba)3 (34 mg, 0.0368 mmol), BINAP (46 mg, 0.0736 mmol), 2,3-dichloro-5-iodopyridine (554 mg, 2.02 mmol), and sodium tert-butoxide (283 mg, 2.94 mmol) were processed according to the procedure described in Example 56A to provide the title compound (110 mg, 0.308 mmol, 17% yield). MS (DCI/NH3) m/z 358 (M+H)+.
  • 5
  • [ 97966-01-3 ]
  • [ 134003-84-2 ]
  • [ 286946-96-1 ]
YieldReaction ConditionsOperation in experiment
The product from Example 15B and 2,3-dichloro-5-iodopyridine, prepared as described in (U.S. Pat. No. 5,733,912) were processed as described in Example 15C to provide the title compound. MS (DCI/NH3) m/z 344 (M+H)+.
  • 7
  • [ 97966-01-3 ]
  • [ 799279-81-5 ]
  • tert-butyl (1S,5R)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With sodium t-butanolate In toluene at 110℃;
  • 8
  • [ 97966-01-3 ]
  • [ 370881-68-8 ]
  • (1R,5R)-benzyl 6-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With sodium t-butanolate In toluene at 110℃;
  • 9
  • [ 97966-01-3 ]
  • (1R,4R)-2-(5,6-dichloro-3-pyridinyl)-2,5-diazabicyclo[2.2.1]heptane p-toluenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tert-butoxide / 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 80 - 85 °C 2: ethyl acetate / Heating
  • 10
  • [ 97966-01-3 ]
  • (1S,6R)-8-(5,6-dichloro-3-pyridinyl)-3,8-diazabicyclo[4.2.0]octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; NaOt-Bu / tris(dibenzylideneacetone)dipalladium / toluene / 80 °C 2: trifluoroacetic acid / CH2Cl2 / 0 - 20 °C
  • 11
  • [ 97966-01-3 ]
  • (cis)-8-(5,6-dichloro-3-pyridinyl)-3,8-diazabicyclo[4.2.0]octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; NaOt-Bu / tris(dibenzylideneacetone)dipalladium / toluene / 80 °C 2: trifluoroacetic acid / CH2Cl2 / 0 - 20 °C
  • 12
  • [ 97966-01-3 ]
  • 3-(5,6-dichloro-pyridin-3-yl)-3,8-diaza-bicyclo[4.2.0]octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; NaOt-Bu / tris(dibenzylideneacetone)dipalladium / toluene / 80 °C 2: trifluoroacetic acid / CH2Cl2 / 0 - 20 °C
  • 13
  • [ 97966-01-3 ]
  • 3-(5,6-dichloro-pyridin-3-yl)-3,8-diaza-bicyclo[4.2.0]octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; NaOt-Bu / tris(dibenzylideneacetone)dipalladium / toluene / 80 °C 2: trifluoroacetic acid / CH2Cl2 / 0 - 20 °C
  • 14
  • [ 97966-01-3 ]
  • tert-butyl (cis)-5-(trimethylstannyl)-3,3a,4,6a-tetrahydrocyclopenta[c]pyrrole-2(1H)-carboxylate [ No CAS ]
  • tert-butyl 5-(5,6-dichloro-3-pyridinyl)-3,3a,4,6a-tetrahydrocyclopenta[c]pyrrole-2(1H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With triphenyl-arsane In 1-methyl-pyrrolidin-2-one at 60℃; for 5h; 6.6.A EXAMPLE 6; (cis)-5-(5,6-dichloro-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole hydrochloride; Example 6A; Tert-butyl 5-(5,6-dichloro-3-pyridinyl-3,3a,4,6a-tetrahydrocyclopenta[c]pyrrole-2(1H)-carboxylate tert-butyl 5-(5,6-dichloro-3-pyridinyl-3,3a,4,6a-tetrahydrocyclopenta[c]pyrrole-2(1H)-carboxylate 2,3-Dichloro-5-iodopyridine (0.288 g, 1.05 mmol), triphenylarsine (0.026 g, 0.084 mmol), and tris(dibenzylideneacetone)dipalladium(0) (0.019 g, 2 mol %) in anhydrous 1-methyl-2-pyrrolidinone (5 ML) were treated with the product from Example 4B (0.392 g, 1.05 mmol) in 1-methyl-2-pyrrolidinone (2 ML).After stirring at 60° C. for 5 hours, the reaction mixture was allowed to cool to ambient temperature and partitioned between ethyl acetate and 1N aqueous sodium hydroxide.The organic extract was separated, washed with 1N aqueous sodium hydroxide, water, brine, dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure.The residue was purified by chromatography (SiO2, 50% ethyl acetate/hexanes) to provide the title compound (0.228 g, 61%). MS (DCI/NH3) m/z 355 (M+H)+.
  • 15
  • [ 97966-01-3 ]
  • [ 370881-43-9 ]
  • 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl [ No CAS ]
  • [ 370882-83-0 ]
YieldReaction ConditionsOperation in experiment
25% With sodium t-butanolate 85.A benzyl (1S,5 S)-6-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate EXAMPLE 85A benzyl (1S,5 S)-6-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate The product of Example 52D (451 mg, 1.94 mmol) was coupled with 2,3-dichloro-5-iodopyridine (805 mg, 2.94 mmol; U.S. Pat. No. 7,733,912) using tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 36 mg, 0.039 mmol; Alfa Aesar), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP, 82 mg, 0.13 mmol; Strem), and sodium tert-butoxide (360 mg, 3.75 mmol; Aldrich) according to the procedure described in Example 1E to provide the title compound (184 mg, 25% yield). MS (DCI/NH3) m/z 378, 380 (M+H)+.
  • 16
  • [ 426463-09-4 ]
  • [ 97966-01-3 ]
YieldReaction ConditionsOperation in experiment
70% With hydrogenchloride; sodium nitrite;copper(l) chloride; 2,3-Dichloro-5-iodopyridine 5-iodo-3-amino-2-chloropyridine (1.212 g, 4.76 mmol) and concentrated HCl (10 mL) were stirred at room temperature for ten minutes. Sodium nitrite (5.3 g, 76.8 mmol) was then slowly added followed by CuCl (4.0 g, 40.4 mmol). Stirring continued for 30 min. The mixture was poured into 1:1 NH4OH:H2O, extracted with ethyl acetate, dried over sodium sulfate, then concentrated. The crude residue was purified by flash chromatography using 95:5 hexane:ethyl acetate to yield 2,3-Dichloro-5-iodopyridine (913 mg, 70%) as a colorless solid. 1H-NMR(CDCl3) delta (ppm) 8.08 (d,J=1.8 Hz, 1H), 8.49 (d,J=1.8 Hz, 1H); 13C NMR (CDCl3) delta (ppm) 90.18, 131.46, 146.03, 148.81, 153.12. Analytical Calculated for C5H2NICl2: C, 21.93; H, 0.74; N, 5.11; Found: C, 21.84; H, 0.74; N, 5.04.
  • 17
  • [ 540-80-7 ]
  • diazonium tetrafluoroborate salt [ No CAS ]
  • Na2 S2 O3 [ No CAS ]
  • [ 98121-41-6 ]
  • [ 97966-01-3 ]
YieldReaction ConditionsOperation in experiment
75% With pyridine; Ki; In 1,2-dimethoxyethane; acetonitrile; pentane; 8a. 2,3-Dichloro-5-iodopyridine <strong>[98121-41-6]5-Amino-2,3-dichloropyridine</strong> (15.0 g, 92.0 mmol, prepared according to V. Koch and S. Schnatterer, Synthesis, 1990, 499-501) was dissolved in DME (30 mL) and subjected to diazotization conditions according to the procedure of M. P. Doyle and W. J. Bryker (Journal Of Organic Chemistry, 1979, 44, 1572). The dissolved pyridine analog was added to a solution of BF3 etherate complex (17 mL, 138 mmol) at -15 C. t-Butyl nitrite in DME (92 mL) was then added at a rate such that the temperature never rose above -5 C. Alter complete addition, the reaction mixture was allowed to warm to 5 C. and stir an additional 45 minutes. Pentane was added and the resultant slurry filtered. The filter cake was washed with cold Et2 O, and the solid was air dried to afford a light orange solid (22.3 g). A sample of the crude diazonium tetrafluoroborate salt (5.1 g, 19.5 mmol) and KI (3.5 g, 21.4 mmol) were combined in CH3 CN (130 mL) and allowed to stir at ambient temperature for 18 hours. A 10% solution of Na2 S2 O3 was carefully added, the biphasic mixture was poured over Et2 O, and the phases were separated. The organic phase was dried (MgSO4) and concentrated, and the residue was chromatographed (silica gel; hexanes/CH2 Cl2, 10:1) to afford a white solid (4.0 g, 75%). mp 55-57 C. Rf =0.43 (hexanes/CH2 Cl2, 2:1). 1 H NMR (CDCl3, 300 MHz) delta8.09 (d, J=1.8 Hz, 1H), 8.5 (d, J=1.8 Hz, 1H).
  • 18
  • [ 97966-01-3 ]
  • 1-azoniabicyclo[3.3.0]oct-1(5)-ene perchlorate [ No CAS ]
  • 7a-(5,6-dichloro-3-pyridinyl)-hexahydro-1H-pyrrolizine [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With hydrogenchloride; tert.-butyl lithium In diethyl ether; pentane 8.b 8b. 8b. 7a-(5,6-dichloro-3-pyridinyl)-hexahydro-1H-pyrrolizine A solution of 1.7M tBuLi (4.7 mL, 8.0 mmol) in pentane was added to 2,3-dichloro-5-iodopyridine (from step 8a, 1.0 g, 3.65 mmol) in Et2 O (15 mL) precooled to -100° C. After stirring for 2 minutes, 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate (1.5 g, 7.3 mmol) was added, and the reaction mixture was allowed to stir for 20 minutes at -100° C. then gradually warm to -20° C. A solution of 2N HCl was added, and the cold bath was removed. After warming to ambient temperature, the reaction mixture was poured over EtOAc and the phases were separated. The aqueous phase was basified with 15% NaOH solution and extracted with CH2 Cl2 (2*). The CH2 Cl2 phases were combined, dried (MgSO4), concentrated and the residue was chromatographed (silica gel; CHCl3 /MeOH, 99.5:0.5) to afford a light yellow oil (510 mg, 54%). MS (CI/NH3) m/e: 257 (M+H)+. 1 H NMR (CDCl3, 300 MHz) δ1.59-1.71 (m, 2H), 1.80-2.08 (m, 6H), 2.64-2.72 (m, 2H), 3.11-3.20 (m, 2H), 7.99 (d, J=2.2 Hz, 1H), 8.36 (d, J=2.2 Hz, 1H).
  • 19
  • [ 54127-63-8 ]
  • 3-chloro-5-iodopyridin-2-ol [ No CAS ]
  • [ 7732-18-5 ]
  • [ 497-19-8 ]
  • [ 97966-01-3 ]
YieldReaction ConditionsOperation in experiment
With I2; Ki; phosphorus pentachloride; trichlorophosphate In dichloromethane 3 Preparation of 2,3-Dichloro-5-iodopyridine STR9 EXAMPLE 3 Preparation of 2,3-Dichloro-5-iodopyridine STR9 Substantially the same procedures described in STEP 1 of Example 2 were employed using 12.6 g (72.6 mmoles) of 5-chloro-6-hydroxynicotinic acid, 12.83 g (121 mmoles) of Na2 CO3, 20.47 g (80.7 mmoles) of I2, 20.09 g (121 mmoles) of KI and 500 ml of H2 O. The reaction produced 17.2 g of a tan solid. STR10 A 100 ml 3-necked round bottom flask, fitted with a condenser topped with a N2 inlet, a mechanical stirrer and a thermometer, was charged with 17.2 g (0.0673 mole) of 3-chloro-2-hydroxy-5-iodopyridine, 14.85 g (0.0713 mole) of PCl5, and 1 ml (1.68 g; 0.0109 mole) of POCl3. The reaction mixture, containing solids, was slowly stirred and slowly heated to 130° C. The reaction mixture was stirred under N2 for 5 hours after which it was cooled to room temperature and allowed to stand overnight. The reaction mixture was cautiously poured into crushed ice and allowed to stand for 1 hour. Methylene chloride (200 ml) was added to the reaction mixture to dissolve the solids present in it. The layers was separated and the organic phase was washed with dilute base, water and saturated NaCl. After drying over anhydrous MgSO4 and filtration, the solvent was evaporated leaving 11.8 g of a yellow solid. The solid was recrystallized from methanol resulting in 6.60 g of solid that had spectral and physical properties identical to the product obtained in Example 1, STEP D.
  • 20
  • [ 54127-63-8 ]
  • 3-chloro-5-iodopyridin-2-ol [ No CAS ]
  • [ 97966-01-3 ]
YieldReaction ConditionsOperation in experiment
With Ki; phosphorus pentachloride; iodine; sodium carbonate; trichlorophosphate In water 2 Preparation of 2,3-Dichloro-5-iodopyridine STR7 EXAMPLE 2 Preparation of 2,3-Dichloro-5-iodopyridine STR7 A 250 ml 3-necked round bottom flask, fitted with a reflux condenser, thermometer, addition funnel and magnetic stirrer, was charged with 3.47 g (0.02 mole) of 5-chloro-6-hydroxynicotinic acid (from Example 1, STEP A) and 8.6 g (0.03 mole) of sodium carbonate in 90 ml of water. The reaction mixture was stirred and heated to 100° C. under N2. A solution of 5.1 g (0.02 mole) of iodine and 5.1 g (0.03 mole) of KI in 35 ml of water was added to the reaction mixture over 0.5 hour to minimize foaming. The reaction mixture was stirred for 1 hour at 100° C. The mixture was cooled to room temperature and the addition funnel was replaced with a gas sparge tube. SO2 was passed through the mixture causing the formation of a tan precipitate. The SO2 addition was maintained until the pH was <1. The slurry was stirred for 1 hour. The precipitate was isolated by filtration, washed with water and air dried resulting in 4.05 g of a tan solid having a melting point of 202°-209° C. STR8 A 50 ml 3-necked round bottom flask, equipped with a thermometer, a reflux condenser topped with a N2 inlet, a stopper and a magnetic stirrer, was charged with 3.50 g (0.0137 mole) of 3-chloro-5-iodo-2-pyridinol, from STEP 1 above, 3.00 g (0.0144 mole) of phosphorus pentachloride and 5-10 ml of phosphorus oxychloride. The reaction mixture was heated to reflux and the solid dissolved resulting in a golden brown solution. The reaction mixture was stirred under N2 at reflux for 4 hours and then cooled to room temperature. The reaction mixture was poured into crushed ice and allowed to stand for about 1 hour. A tan precipitate, which was shown to be product and unreacted starting material, formed and was isolated by filtration and washed with pentane. The aqueous layer was also washed with pentane. The combined organic layers were washed with deionized water and saturated NaCl, dried over anhydrous MgSO4, filtered and evaporated to dryness to give 0.4 g of a dark oil that crystallized upon standing.
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 97966-01-3 ]

Chlorides

Chemical Structure| 942206-23-7

[ 942206-23-7 ]

2,5-Dichloro-3-iodopyridine

Similarity: 0.87

Chemical Structure| 69045-79-0

[ 69045-79-0 ]

2-Chloro-5-iodopyridine

Similarity: 0.84

Chemical Structure| 889865-45-6

[ 889865-45-6 ]

2,3-Dichloro-4-iodopyridine

Similarity: 0.83

Chemical Structure| 942206-23-7

[ 942206-23-7 ]

2,5-Dichloro-3-iodopyridine

Similarity: 0.87

Chemical Structure| 69045-79-0

[ 69045-79-0 ]

2-Chloro-5-iodopyridine

Similarity: 0.84

Iodides

Chemical Structure| 942206-23-7

[ 942206-23-7 ]

2,5-Dichloro-3-iodopyridine

Similarity: 0.87

Chemical Structure| 69045-79-0

[ 69045-79-0 ]

2-Chloro-5-iodopyridine

Similarity: 0.84

Chemical Structure| 889865-45-6

[ 889865-45-6 ]

2,3-Dichloro-4-iodopyridine

Similarity: 0.83

Chemical Structure| 942206-23-7

[ 942206-23-7 ]

2,5-Dichloro-3-iodopyridine

Similarity: 0.87

Chemical Structure| 69045-79-0

[ 69045-79-0 ]

2-Chloro-5-iodopyridine

Similarity: 0.84

Related Parent Nucleus of
[ 97966-01-3 ]

Pyridines

Chemical Structure| 942206-23-7

[ 942206-23-7 ]

2,5-Dichloro-3-iodopyridine

Similarity: 0.87

Chemical Structure| 69045-79-0

[ 69045-79-0 ]

2-Chloro-5-iodopyridine

Similarity: 0.84

Chemical Structure| 889865-45-6

[ 889865-45-6 ]

2,3-Dichloro-4-iodopyridine

Similarity: 0.83

Chemical Structure| 942206-23-7

[ 942206-23-7 ]

2,5-Dichloro-3-iodopyridine

Similarity: 0.87

Chemical Structure| 69045-79-0

[ 69045-79-0 ]

2-Chloro-5-iodopyridine

Similarity: 0.84