Home Cart 0 Sign in  
X

[ CAS No. 186593-54-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 186593-54-4
Chemical Structure| 186593-54-4
Chemical Structure| 186593-54-4
Structure of 186593-54-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 186593-54-4 ]

Related Doc. of [ 186593-54-4 ]

Alternatived Products of [ 186593-54-4 ]

Product Details of [ 186593-54-4 ]

CAS No. :186593-54-4 MDL No. :MFCD08061303
Formula : C5H3BrFNO Boiling Point : -
Linear Structure Formula :- InChI Key :APZDTSYBPUWQHB-UHFFFAOYSA-N
M.W : 191.99 Pubchem ID :18458777
Synonyms :

Calculated chemistry of [ 186593-54-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 33.92
TPSA : 33.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.28
Log Po/w (XLOGP3) : 1.62
Log Po/w (WLOGP) : 2.11
Log Po/w (MLOGP) : 1.02
Log Po/w (SILICOS-IT) : 2.05
Consensus Log Po/w : 1.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.54
Solubility : 0.548 mg/ml ; 0.00286 mol/l
Class : Soluble
Log S (Ali) : -1.93
Solubility : 2.27 mg/ml ; 0.0118 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.58
Solubility : 0.5 mg/ml ; 0.00261 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.84

Safety of [ 186593-54-4 ]

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

Application In Synthesis of [ 186593-54-4 ]

* 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 [ 186593-54-4 ]

[ 186593-54-4 ] Synthesis Path-Downstream   1~15

YieldReaction ConditionsOperation in experiment
54.c 5-bromo-6-fluoro-3-(3-(S)-pyrrolidinylmethoxy)pyridine dihydrochloride was prepared in the following manner. 54c. 3-bromo-2-fluoro-5-hydroxypyridine was then prepared as follows. The compound from step 54b above (3.0 g 15.9 mmol) is dissolved in 50 ml of HF pyridine (Aldrich) and cooled to 0° C. under nitrogen and sodium nitrite (1.09 g 15.8 mmol) is added in portions over 20 minutes. The reaction is heated to 50° C. for one hour, cooled to 0° C. and then basified with 20% sodium hydroxide. The aqueous phase is washed with methylene chloride (5*100 ml), neutralized with HCl (pH=7), and extracted with ethyl acetate (5*100 ml). These extracts are dried (MgSO4), filtered, and concentrated in vacuo to yield the title compound as a tan solid. MS (DCI/NH3) m/e 192-194 (M+H)+. 1H-NMR (DMSO-d6, 300 MHz) δ9.38 (d, J=2.6 Hz, 1H), 9.20-9.19 (d, J=2.6 Hz, 1H).
106.c 106c. 106c. 3-bromo-2-fluoro-5-hydroxypyridine The compound from step 106b above (3.0 g 15.9 mmol) was dissolved in 50 ml of HF pyridine (Aldrich) and cooled to 0° C. under nitrogen and sodium nitrite (1.09 g 15.8 mmol) was added in portions over 20 min. The reaction was heated to 50° C. for one hour, cooled to 0° C. and then basified with 20% sodium hydroxide. The aqueous phase was washed with CH2 Cl2 (5*100 ml), neutralized with HCl (pH=7), and extracted with EtOAc (5*100 ml). These extracts were dried (MgSO4), filtered, and concentrated in vacuo yielding the title compound as a tan solid. MS (CI/NH3) m/e 192/194 (M+H)+. 1 H NMR (DMSO-d6, 300 MHz) δ9.38 (d, J=2.6 Hz, 1H), 9.20-9.19 (d, J=2.6 Hz, 1H).
106.c 106c. 106c. 3-bromo-2-fluoro-5-hydroxypyridine The compound from step 106b above (3.0 g 15.9 mmol) was dissolved in 50 ml of HF pyridine (Aldrich) and cooled to 0° C. under nitrogen and sodium nitrite (1.09 g 15.8 mmol) was added in portions over 20 min. The reaction was heated to 50° C. for one hour, cooled to 0° C. and then basified with 20% sodium hydroxide. The aqueous phase was washed with methylene chloride (5*100 ml), neutralized with HCl (pH=7), and extracted with ethyl acetate (5*100 ml). These extracts were dried (MgSO4), filtered, and concentrated in vacuo yielding the title compound as a tan solid. MS (DCI/NH3) m/e 192-194 (M+H)+. 1 H NMR (DMSO-d6, 300 MHz) δ: 9.38 (d, J=2.6 Hz, 1H), 9.20-9.19 (d, J=2.6 Hz, 1H).
106.c 106c. 106c. 3-Bromo-2-fluoro-5-hydroxypyridine The compound from step 106b above (3.0 g 15.9 mmol) was dissolved in 50 ml of HF pyridine (Aldrich) and cooled to 0° C. under nitrogen and sodium nitrite (1.09 g 15.8 mmol) was added in portions over 20 min. The reaction was heated to 50° C. for one hour, cooled to 0° C. and then basified with 20% sodium hydroxide. The aqueous phase was washed with CH2Cl2 (5*100 ml), neutralized with HCl (pH=7), and extracted with EtOAc (5*100 ml). These extracts were dried (MgSO4), filtered, and concentrated in vacuo yielding the title compound as a tan solid. MS (CI/NH3) m/e 192/194 (M+H)+. 1H NMR (DMSO-d6, 300 MHz) δ: 9.38 (d, J=2.6 Hz, 1H), 9.20-9.19 (d, J=2.6 Hz, 1H).
31.d 31d. 31d. 3-Bromo-2-fluoro-5-hydroxypyridine The compound from 31c (3.0 g, 15.9 mmol) was dissolved in HF.pyridine (50 mL). The solution was cooled to 0° C. and stirred under nitrogen, then sodium nitrite (1.09 g, 15.8 mmol) was added in portions over 20 minutes. The mixture was heated to 50° C. for 1 hour, cooled to 0° C. and basified with 20% aqueous NaOH. The aqueous phase was washed with methylene chloride (5*100 mL), neutralized with HCl, and extracted with ethyl acetate (5*100 mL). The organic extracts were dried (MgSO4), filtered and concentrated in vacuo, yielding the title compound as a tan solid: MS (CI/NH3) m/z 192, 194 (M+H)+. 1 H NMR (DMSO-d6, 300 MHz) δ 9.38 (d, J=2.6 Hz, 1H), 9.20 (d, J=2.6 Hz, 1 H).

  • 2
  • [ 186593-54-4 ]
  • [ 387845-16-1 ]
  • [ 945601-81-0 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In butanone for 20h; Reflux; 4 Preparation 4tert-Butyl(1-[(5-bromo-6-fluoropyridin-3-yl)oxy]methyl}cyclopropyl)methylcarbamate12.9 g of caesium carbonate are added to a solution of 10.5 g of the compound obtained in Step 4 of Preparation 1 and 5.8 g of 5-bromo-6-fluororopyridin-3-ol in 300 ml of butanone. The reaction mixture is heated for 20 hours at reflux and then filtered and concentrated. The residue is taken up in dichloromethane. After washing with saturated sodium chloride solution and drying over sodium sulphate, the organic phase is concentrated. Chromatography on silica gel (dichloromethane/butanone: 98/2) allows 10.7 g of the expected product to be obtained.
  • 3
  • [ 186593-54-4 ]
  • [ 2231231-97-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sulfuric acid; potassium nitrate / 16 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: iron; acetic acid / 2 h / 20 °C 4.1: dmap / 12 h / 100 °C
  • 4
  • [ 186593-54-4 ]
  • [ 2231231-98-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sulfuric acid; potassium nitrate / 16 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: iron; acetic acid / 2 h / 20 °C 4.1: potassium fluoride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; dimethyl sulfoxide / 16 h / 120 °C / Inert atmosphere 5.1: dmap / 16 h / 100 °C
  • 5
  • [ 186593-54-4 ]
  • [ 2231233-93-3 ]
YieldReaction ConditionsOperation in experiment
56% With sulfuric acid; potassium nitrate at 20℃; for 16h; A.31.1 Step 1- Synthesis of 5-bromo-6-fluoro-2-nitro-pyridin-3-ol X-31 a To a solution of H2S04 (15 ml) was added KN03 (0.63 g, 6.28 mmol) and the reactionmixture was stirred at room temperature for 20 min. 5-bromo-6-fluoro-pyridin-3-ol (0.60 g,3.14 mmol) was added and the reaction mixture was stirred at room temperature for 16h.Progress of reaction was monitored by TLC. After completion, the reaction mixture was25 poured into ice (1 00 ml) and extracted with EtOAc (3 x 80 ml). The organic layer wasseparated, washed with brine (120 ml), dried over anhydrous Na2S04 and concentratedunder vacuum to afford 5-bromo-6-fluoro-2-nitro-pyridin-3-ol X-31a (0.60 g) as an off-whitesolid.Yield: 56%1H NMR (400 MHz, DMSO-d6) o 8.11 (d, J=7.2 Hz, 1 H) 11.83 (brs, 1 H).
  • 6
  • [ 186593-54-4 ]
  • [ 2231233-94-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sulfuric acid; potassium nitrate / 16 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 16 h / 0 - 20 °C
  • 7
  • [ 186593-54-4 ]
  • [ 2231233-95-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sulfuric acid; potassium nitrate / 16 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: iron; acetic acid / 2 h / 20 °C
  • 8
  • [ 186593-54-4 ]
  • [ 2231233-96-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sulfuric acid; potassium nitrate / 16 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: iron; acetic acid / 2 h / 20 °C 4.1: potassium fluoride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; dimethyl sulfoxide / 16 h / 120 °C / Inert atmosphere
  • 9
  • 3-bromo-2-fluoro-5-hydroxypyridine [ No CAS ]
  • [ 161511-85-9 ]
  • [ 209328-68-7 ]
YieldReaction ConditionsOperation in experiment
72.3% With triphenylphosphine; In tetrahydrofuran; 31a. 5-((2S)-azetidinylmethoxy)-3-bromo-2-fluoropyridine dibenzoate To a solution of diethyl azodicarboxylate (0.7 mL, 4.4 mmol) in THF (25 mL) was added triphenylphosphine (1.19 g, 4.4 mmol) at 0 C., and the reaction mixture was stirred for 0.5 hour. 1-t-Butyloxycarbonyl-(2S)-azetidinemethanol (0.85 g, 4.5 mmol, Example 7c) and 5-bromo-6-fluoropyridin-3-ol (0.75 g, 4.0 mmol, Step 31d) were then added. The reaction mixture was allowed to warm slowly to room temperature and stirred overnight. The solvent was removed, and the residue was chromatographed (silica gel, hexane/ethyl acetate, 5:1) to afford 5-bromo-6-fluoro-3-(1-t-butyloxycarbonyl-(2S)-azetidinylmethoxy)pyridine (1.02 g, 72.3%): MS (CI/NH3) m/z 362, 379 (M+H)+, (M+NH4+); 1 H NMR (CDCl3 300 MHz) δ 7.82 (m, 1H), 7.60 (dd, J=3.1, 7.1 Hz 1H), 4.51 (m, 1H), 4.35 (m, 1H), 4.11 (dd, J=3.1, 10.2 Hz, 1H), 3.88 (m, 2H), 2.33 (m, 2H), 1.45 (s, 9H).
  • 10
  • [ 186593-54-4 ]
  • [ 74-88-4 ]
  • [ 1227578-33-7 ]
YieldReaction ConditionsOperation in experiment
93% With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 4h; A.A.4.1 Step-1 : Synthesis of 3-bromo-2-fluoro-5-methoxy-pyridine X-4a: To a solution of 5-bromo-6-fluoro-pyridin-3-ol (0.80 g, 4.17 mmol) and NaH (0.33 g, 8.33 mmol) in DMF (15 mL) was added CH3I (0.31 mL, 5.00 mmol) drop wise at 0 °C. The reaction mixture was stirred at room temperature for 4h. Progress of reaction was monitored by TLC and LCMS. After completion, the reaction mixture was poured into cold H20 (20 mL) and extracted with EtOAc (2 c 30 mL). The organic layer was separated, washed with brine (20 mL), dried over anhydrous Na2S04 and concentrated under vacuum. The crude obtained was purified by combi-flash column chromatography (30% EtOAc in hexane) to afford 3-bromo-2-fluoro-5-methoxy-pyridine X-4a (0.80 g) as a pale yellow solid. Yield: 93%. (0762) Basic LCMS Method 2 (ES+): 206 (M+H)+, 99% purity. (0763) 1H NMR (400 MHz, DMSO-cfe) d 3.85 (s, 3H), 7.92 (t, J=2.20 Hz, 1 H), 7.99 (dd, J=7.34, 2.20 Hz, 1 H).
  • 11
  • [ 186593-54-4 ]
  • [ 2407470-08-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 4 h / 0 - 20 °C 2.1: urea hydrogen peroxide / dichloromethane / 0.17 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 16 h / 0 - 20 °C 4.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 0.33 h / Inert atmosphere 4.2: 16 h / 100 °C / Inert atmosphere 5.1: hydrogenchloride / methanol / 3 h / 0 - 20 °C 6.1: dmap; pyridine / 16 h / 90 °C
  • 12
  • [ 186593-54-4 ]
  • [ 2407470-81-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 4 h / 0 - 20 °C 2.1: urea hydrogen peroxide / dichloromethane / 0.17 h / 0 °C 2.2: 16 h / 0 - 20 °C
  • 13
  • [ 186593-54-4 ]
  • [ 1823371-97-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 4 h / 0 - 20 °C 2.1: urea hydrogen peroxide / dichloromethane / 0.17 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 16 h / 0 - 20 °C
  • 14
  • [ 186593-54-4 ]
  • [ 2407470-82-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 4 h / 0 - 20 °C 2.1: urea hydrogen peroxide / dichloromethane / 0.17 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 16 h / 0 - 20 °C 4.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 0.33 h / Inert atmosphere 4.2: 16 h / 100 °C / Inert atmosphere
  • 15
  • [ 186593-54-4 ]
  • [ 2407470-83-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 4 h / 0 - 20 °C 2.1: urea hydrogen peroxide / dichloromethane / 0.17 h / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 16 h / 0 - 20 °C 4.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 0.33 h / Inert atmosphere 4.2: 16 h / 100 °C / Inert atmosphere 5.1: hydrogenchloride / methanol / 3 h / 0 - 20 °C
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 186593-54-4 ]

Fluorinated Building Blocks

Chemical Structure| 55758-32-2

[ 55758-32-2 ]

6-Fluoropyridin-3-ol

Similarity: 0.78

Chemical Structure| 1421602-80-3

[ 1421602-80-3 ]

2,4-Dibromo-6-fluoropyridin-3-ol

Similarity: 0.75

Chemical Structure| 209328-99-4

[ 209328-99-4 ]

5-Bromo-6-fluoropyridin-3-amine

Similarity: 0.73

Chemical Structure| 1227577-18-5

[ 1227577-18-5 ]

6-Fluoro-4-methylpyridin-3-ol

Similarity: 0.69

Chemical Structure| 209328-85-8

[ 209328-85-8 ]

2,6-Difluoropyridin-3-ol

Similarity: 0.64

Bromides

Chemical Structure| 1421602-80-3

[ 1421602-80-3 ]

2,4-Dibromo-6-fluoropyridin-3-ol

Similarity: 0.75

Chemical Structure| 209328-99-4

[ 209328-99-4 ]

5-Bromo-6-fluoropyridin-3-amine

Similarity: 0.73

Chemical Structure| 857429-79-9

[ 857429-79-9 ]

2,5-Dibromopyridin-3-ol

Similarity: 0.72

Chemical Structure| 91420-25-6

[ 91420-25-6 ]

5-Bromo-2-methylpyridin-3-ol

Similarity: 0.71

Chemical Structure| 286946-77-8

[ 286946-77-8 ]

5-Bromo-2-chloropyridin-3-ol

Similarity: 0.71

Alcohols

Chemical Structure| 55758-32-2

[ 55758-32-2 ]

6-Fluoropyridin-3-ol

Similarity: 0.78

Chemical Structure| 1421602-80-3

[ 1421602-80-3 ]

2,4-Dibromo-6-fluoropyridin-3-ol

Similarity: 0.75

Chemical Structure| 857429-79-9

[ 857429-79-9 ]

2,5-Dibromopyridin-3-ol

Similarity: 0.72

Chemical Structure| 91420-25-6

[ 91420-25-6 ]

5-Bromo-2-methylpyridin-3-ol

Similarity: 0.71

Chemical Structure| 286946-77-8

[ 286946-77-8 ]

5-Bromo-2-chloropyridin-3-ol

Similarity: 0.71

Related Parent Nucleus of
[ 186593-54-4 ]

Pyridines

Chemical Structure| 55758-32-2

[ 55758-32-2 ]

6-Fluoropyridin-3-ol

Similarity: 0.78

Chemical Structure| 1421602-80-3

[ 1421602-80-3 ]

2,4-Dibromo-6-fluoropyridin-3-ol

Similarity: 0.75

Chemical Structure| 209328-99-4

[ 209328-99-4 ]

5-Bromo-6-fluoropyridin-3-amine

Similarity: 0.73

Chemical Structure| 857429-79-9

[ 857429-79-9 ]

2,5-Dibromopyridin-3-ol

Similarity: 0.72

Chemical Structure| 91420-25-6

[ 91420-25-6 ]

5-Bromo-2-methylpyridin-3-ol

Similarity: 0.71