Home Cart 0 Sign in  
X

[ CAS No. 887707-25-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 887707-25-7
Chemical Structure| 887707-25-7
Chemical Structure| 887707-25-7
Structure of 887707-25-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 887707-25-7 ]

Related Doc. of [ 887707-25-7 ]

Alternatived Products of [ 887707-25-7 ]

Product Details of [ 887707-25-7 ]

CAS No. :887707-25-7 MDL No. :MFCD12024302
Formula : C6H2ClF3IN Boiling Point : -
Linear Structure Formula :- InChI Key :KUASPTUGCBGXAE-UHFFFAOYSA-N
M.W : 307.44 Pubchem ID :11500513
Synonyms :

Calculated chemistry of [ 887707-25-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
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) : -5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.11
Log Po/w (XLOGP3) : 3.35
Log Po/w (WLOGP) : 4.51
Log Po/w (MLOGP) : 3.05
Log Po/w (SILICOS-IT) : 4.01
Consensus Log Po/w : 3.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.16
Solubility : 0.0212 mg/ml ; 0.0000691 mol/l
Class : Moderately soluble
Log S (Ali) : -3.3
Solubility : 0.155 mg/ml ; 0.000503 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.46
Solubility : 0.0106 mg/ml ; 0.0000344 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.16

Safety of [ 887707-25-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 887707-25-7 ]

* 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.

  • Upstream synthesis route of [ 887707-25-7 ]
  • Downstream synthetic route of [ 887707-25-7 ]

[ 887707-25-7 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 887707-23-5 ]
  • [ 887707-25-7 ]
YieldReaction ConditionsOperation in experiment
63% at 100℃; Step B. 2-chloro-5-iodo-3-(trifluoromethyl)Dyridine A suspension of 5-iodo-3-(trifluoromethyl)pyridin-2-ol (3.0 g, 10.4 mmol) in POCI3 (8 mL) was heated at 100 °C overnight. After cooling down to room temperature, the mixture was poured into ice (50 g). The resulting aqueous layer was neutralized by Na2C03 and extracted with ethyl acetate (70 mL x 2). The extracts were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether:EtOAc (100: 1-4: 1) as eluting solvents to afford 2- chloro-5-iodo-3-(trifluoromethyl)pyridine as a white solid (2.0 g, 63percent). 1H NMR (500 MHz, CDCls) δ (ppm) 8.78 (d, J = 2.0 Hz, 1H), 8.28 (d, J = 2.0 Hz, 1H).
63% at 100℃; Step B. 2-chloro-5-iodo-3-(trifluoromethyl)pyridine A suspension of 5-iodo-3-(trifluoromethyl)pyridin-2-ol (3.0 g, 10.4 mmol) in POCI3 (8 mL) was heated at 100 °C overnight. After cooling down to room temperature, the mixture was poured into ice (50 g). The resulting aqueous layer was neutralized by Na2C03 and extracted with EtOAc (70 mL x 2). The extracts were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether:EtOAc (100: 1-4: 1) as eluting solvents to afford 2- chloro-5-iodo-3-(trifluoromethyl)pyridine as a white solid (2.0 g, 63percent). 1H NMR (500 MHz, CDC13) δ (ppm) 8.78 (d, / = 2.0 Hz, 1H), 8.28 (d, / = 2.0 Hz, 1H).
62% With trichlorophosphate In N,N-dimethyl-formamide at 110℃; for 0.333333 h; Microwave irradiation 2-choro-5-iodo-3-trifluoromethylpyridine[0072] To an ice-cold mixture OfPOCl3 (1.60 mL) and DMF (1 mL) in a microwave vial, 5-iodo-3-trifluoromethyl-2-pyridinol (1 g, 3.47 mmol) is added. The vial is sealed and heated 20 min at 110 0C. The reaction mixture cooled at room temperature is poured into ice cold water. The product precipitates. The precipitate is filtered, washed with cold water and dried to afford 661 mg (62 percent) of a light brown powder. <n="51"/>[0073] 1U NMR (500 MHz CDCl3) δ 8.32 (d, J=2.0 Hz, IH), 8.81 (d, J=2.0 Hz,IH). 13C NMR (250 MHz CDCl3) δ 89.4, 121.2 (q, JC-F= 273.3 Hz), 126.8 (q, JC-F= 33.6 Hz), 144.34, 148.5, 158.7.
55% With trichlorophosphate In N,N-dimethyl-formamide at 130℃; for 0.333333 h; Microwave irradiation Then in DMF, 2-hydroxy-3-trifluoromethyl-5- (iodo) pyridine I wasmixed with POCl3, and was heated for 20 minutes in a microwave at130 ° C, and 2-chloro-3-trifluoromethyl -5 - (iodo) pyridine J (yield of 50percent to55percent) is formed.
55% With trichlorophosphate In N,N-dimethyl-formamide at 130℃; for 0.333333 h; Microwave irradiation A solution of 2-hydroxy-3-(trifluoromethyl)pyridine C in a mixture of N-iodosuccinimide (NIS), acetonitrile, and dimethylformamide (DMF) is heated at 80° C. for 2 hours to produce 2-hydroxy-3-trifluoromethyl-5-(iodo)pyridine I (greater than 80percent yield). The 2-hydroxy-3-trifluoromethyl-5-(iodo)pyridine I is then mixed with POCl3 in DMF and heated to 130° C. in a microwave for 20 minutes to produce 2-chloro-3-trifluoromethyl-5-(iodo)pyridine J (yield of 50 to 55percent). The 2-chloro-3-trifluoromethyl-5-(iodo)pyridine K is reacted in a solution of pMBnNH2, palladium(II) acetate, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP), triethylamine, and cesium carbonate in toluene to produce 5-((4-methoxyphenyl))methylamino)-2-chloro-3-(trifluoromethyl)pyridine K (yield of 40percent). The 5-((4-methoxyphenyl))methylamino)-2-chloro-3-(trifluoromethyl)pyridine K is reacted in a solution of zinc cyanide, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), and 1,1′-bis(diphenylphosphino)ferrocene (dppf) in DMF to provide 5-(4-methoxybenzylamine)-2-cyano-3-(trifluoromethyl)pyridine K (yield of 92percent). The 5-(4-methoxybenzylamine)-2-cyano-3-(trifluoromethyl)pyridine K is reacted in a solution of dichloromethane and trifluoroacetic acid to provide 2-cyano-3-trifluoromethyl-5-(amino)pyridine H (yield greater than 95percent). The 2-cyano-3-trifluoromethyl-5-(amino)pyridine H is reacted with thiophosgene in water at 25° C. for 2 hours to provide 5-isothiocyanato-3-(trifluoromethyl)pyridine-2-carbonitrile A (yield of 74percent to 95percent).

Reference: [1] Patent: WO2015/100613, 2015, A1, . Location in patent: Page/Page column 17; 18
[2] Patent: WO2015/100617, 2015, A1, . Location in patent: Page/Page column 36; 37
[3] Patent: WO2008/119015, 2008, A2, . Location in patent: Page/Page column 48-49
[4] Patent: JP2016/11315, 2016, A, . Location in patent: Paragraph 0084
[5] Patent: US9388159, 2016, B2, . Location in patent: Page/Page column 20; 21
[6] Synthetic Communications, 2006, vol. 36, # 9, p. 1235 - 1245
[7] Patent: WO2009/18656, 2009, A1, . Location in patent: Page/Page column 53-54
[8] Patent: WO2009/18657, 2009, A1, . Location in patent: Page/Page column 63; 64
[9] Patent: WO2009/76747, 2009, A1, . Location in patent: Page/Page column 62-63
[10] Patent: WO2011/103202, 2011, A2, . Location in patent: Page/Page column 157
[11] Patent: WO2015/196144, , A2, . Location in patent: Paragraph 0326[11] Patent: , 2015, , . Location in patent: Paragraph 0326
[13] Patent: US2008/45516, 2008, A1, . Location in patent: Page/Page column 30
  • 2
  • [ 22245-83-6 ]
  • [ 887707-25-7 ]
Reference: [1] Synthetic Communications, 2006, vol. 36, # 9, p. 1235 - 1245
[2] Patent: WO2015/100613, 2015, A1,
[3] Patent: WO2015/100617, 2015, A1,
[4] Patent: WO2015/196144, , A2, [4] Patent: , 2015, ,
[6] Patent: JP2016/11315, 2016, A,
[7] Patent: US9388159, 2016, B2,
[8] Patent: US2008/45516, 2008, A1,
[9] Patent: WO2008/119015, 2008, A2,
  • 3
  • [ 65753-47-1 ]
  • [ 887707-25-7 ]
Reference: [1] Synthetic Communications, 2006, vol. 36, # 9, p. 1235 - 1245
  • 4
  • [ 887707-25-7 ]
  • [ 573762-62-6 ]
Reference: [1] Patent: WO2011/103202, 2011, A2,
[2] Patent: US9388159, 2016, B2,
[3] Patent: WO2008/119015, 2008, A2,
  • 5
  • [ 887707-25-7 ]
  • [ 109-94-4 ]
  • [ 1113049-90-3 ]
Reference: [1] Patent: WO2009/18657, 2009, A1, . Location in patent: Page/Page column 71
[2] Patent: WO2009/76747, 2009, A1, . Location in patent: Page/Page column 63
Same Skeleton Products
Historical Records

Pharmaceutical Intermediates of
[ 887707-25-7 ]

Apalutamide Intermediates

Chemical Structure| 573762-62-6

[ 573762-62-6 ]

5-Amino-3-(trifluoromethyl)picolinonitrile

Chemical Structure| 99368-67-9

[ 99368-67-9 ]

2-Chloro-5-nitro-3-(trifluoromethyl)pyridine

Chemical Structure| 915087-25-1

[ 915087-25-1 ]

4-Amino-2-fluoro-N-methylbenzamide

Chemical Structure| 99368-66-8

[ 99368-66-8 ]

5-Nitro-3-(trifluoromethyl)pyridin-2-ol

Chemical Structure| 22245-83-6

[ 22245-83-6 ]

3-(Trifluoromethyl)pyridin-2-ol

Apalutamide Intermediates

Chemical Structure| 573762-62-6

[ 573762-62-6 ]

5-Amino-3-(trifluoromethyl)picolinonitrile

Chemical Structure| 99368-67-9

[ 99368-67-9 ]

2-Chloro-5-nitro-3-(trifluoromethyl)pyridine

Chemical Structure| 915087-25-1

[ 915087-25-1 ]

4-Amino-2-fluoro-N-methylbenzamide

Chemical Structure| 99368-66-8

[ 99368-66-8 ]

5-Nitro-3-(trifluoromethyl)pyridin-2-ol

Chemical Structure| 22245-83-6

[ 22245-83-6 ]

3-(Trifluoromethyl)pyridin-2-ol

Related Functional Groups of
[ 887707-25-7 ]

Fluorinated Building Blocks

Chemical Structure| 65753-47-1

[ 65753-47-1 ]

2-Chloro-3-(trifluoromethyl)pyridine

Similarity: 0.83

Chemical Structure| 70158-59-7

[ 70158-59-7 ]

2,5-Dichloro-3-(trifluoromethyl)pyridine

Similarity: 0.78

Chemical Structure| 211122-40-6

[ 211122-40-6 ]

5-Bromo-2-chloro-3-(trifluoromethyl)pyridine

Similarity: 0.74

Chemical Structure| 1211578-93-6

[ 1211578-93-6 ]

6-Chloro-5-(trifluoromethyl)pyridin-3-ol

Similarity: 0.73

Chemical Structure| 55304-75-1

[ 55304-75-1 ]

2,6-Dichloro-3-(trifluoromethyl)pyridine

Similarity: 0.72

Chlorides

Chemical Structure| 65753-47-1

[ 65753-47-1 ]

2-Chloro-3-(trifluoromethyl)pyridine

Similarity: 0.83

Chemical Structure| 59782-89-7

[ 59782-89-7 ]

2-Chloro-5-iodo-3-methylpyridine

Similarity: 0.80

Chemical Structure| 70158-59-7

[ 70158-59-7 ]

2,5-Dichloro-3-(trifluoromethyl)pyridine

Similarity: 0.78

Chemical Structure| 211122-40-6

[ 211122-40-6 ]

5-Bromo-2-chloro-3-(trifluoromethyl)pyridine

Similarity: 0.74

Chemical Structure| 1211578-93-6

[ 1211578-93-6 ]

6-Chloro-5-(trifluoromethyl)pyridin-3-ol

Similarity: 0.73

Trifluoromethyls

Chemical Structure| 65753-47-1

[ 65753-47-1 ]

2-Chloro-3-(trifluoromethyl)pyridine

Similarity: 0.83

Chemical Structure| 70158-59-7

[ 70158-59-7 ]

2,5-Dichloro-3-(trifluoromethyl)pyridine

Similarity: 0.78

Chemical Structure| 211122-40-6

[ 211122-40-6 ]

5-Bromo-2-chloro-3-(trifluoromethyl)pyridine

Similarity: 0.74

Chemical Structure| 1211578-93-6

[ 1211578-93-6 ]

6-Chloro-5-(trifluoromethyl)pyridin-3-ol

Similarity: 0.73

Chemical Structure| 55304-75-1

[ 55304-75-1 ]

2,6-Dichloro-3-(trifluoromethyl)pyridine

Similarity: 0.72

Related Parent Nucleus of
[ 887707-25-7 ]

Pyridines

Chemical Structure| 65753-47-1

[ 65753-47-1 ]

2-Chloro-3-(trifluoromethyl)pyridine

Similarity: 0.83

Chemical Structure| 59782-89-7

[ 59782-89-7 ]

2-Chloro-5-iodo-3-methylpyridine

Similarity: 0.80

Chemical Structure| 70158-59-7

[ 70158-59-7 ]

2,5-Dichloro-3-(trifluoromethyl)pyridine

Similarity: 0.78

Chemical Structure| 211122-40-6

[ 211122-40-6 ]

5-Bromo-2-chloro-3-(trifluoromethyl)pyridine

Similarity: 0.74

Chemical Structure| 1211578-93-6

[ 1211578-93-6 ]

6-Chloro-5-(trifluoromethyl)pyridin-3-ol

Similarity: 0.73