Home Cart 0 Sign in  

[ CAS No. 79762-54-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 79762-54-2
Chemical Structure| 79762-54-2
Structure of 79762-54-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 79762-54-2 ]

Related Doc. of [ 79762-54-2 ]

Alternatived Products of [ 79762-54-2 ]

Product Details of [ 79762-54-2 ]

CAS No. :79762-54-2 MDL No. :MFCD03265457
Formula : C7H5BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :WMKDUJVLNZANRN-UHFFFAOYSA-N
M.W :197.03 Pubchem ID :17842471
Synonyms :

Calculated chemistry of [ 79762-54-2 ]

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 : 1.0
Molar Refractivity : 43.79
TPSA : 28.68 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) : -5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.34
Log Po/w (XLOGP3) : 2.92
Log Po/w (WLOGP) : 2.33
Log Po/w (MLOGP) : 1.88
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.57
Solubility : 0.0534 mg/ml ; 0.000271 mol/l
Class : Soluble
Log S (Ali) : -3.18
Solubility : 0.129 mg/ml ; 0.000655 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0337 mg/ml ; 0.000171 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 79762-54-2 ]

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

Application In Synthesis of [ 79762-54-2 ]

* 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 [ 79762-54-2 ]
  • Downstream synthetic route of [ 79762-54-2 ]

[ 79762-54-2 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 57848-46-1 ]
  • [ 79762-54-2 ]
YieldReaction ConditionsOperation in experiment
89.1% for 20 h; Reflux 2-Fluoro-4-bromobenzaldehyde (20.0 g, 98.5 mmol) was suspended in hydrazine hydrate (100 mL) and heated under reflux for 20 hours. Cooling to room temperature to produce a large number of precipitates,The precipitate was collected by filtration and washed with water, and dried to give the title compound (17.3 g, 89.1percent).
85% With hydrazine In 1,2-dimethoxyethaneReflux A solution of 2-fluoro-4-bromobenzaldehyde (5.09g, 25 mmol) was dissolved in glyme (25 mE) and slowlytreated over 10 minutes with anhydrous hydrazine (25 mE,0.8 mol, 32 eq.).11274] The resulting biphasic mixture was then held at reflux overnight. The reflux condenser was replaced with a short-path distillation head and about half the solvent distilled, at which time the reaction flask showed one phase and two phases were evident in the distillate. The undistilled residue was cooled and treated with water (25 mE), forming a white precipitate. This solid was collected by filtration, washed thoroughly with water, and dried in vacuo to give 6-bromoindazole (4.21 g, 85percent) as white crystals.
76% at 125℃; for 3 h; To a 100 mL round-bottomed flask was added hydrazine (30 mL, 832 mmol) and 4-bromo-2-fluorobenzaldehyde (4.69 g, 23 mmol). The solution was stirred at 125° C. for 3 hours. After cooling to ambient temperature, the solution was concentrated under reduced pressure. The solution was quenched by pouring it into a mixture of ice water (100 mL), and then extracting with EtOAc (3.x.100 mL). The organic layers were combined, dried over sodium sulfate, and filtered. The solution was evaporated to dryness, and adsorbed onto silica gel. The crude product was purified using column chromatography through a Redi-Sep.(R). pre-packed silica gel column (40 g), eluting with a gradient of 0percent to 100percent EtOAc in hexanes, to provide 6-bromo-1H-indazole (4.6 g, 18 mmol, 76percent yield). LCMS (M+H) 197.9 calc. for C7H5BrN2 197.0, 1H NMR (400 MHz, CD3OD): δ ppm 8.03 (s, 1H), 7.67-7.72 (2H, m), 7.24-7.26 (m, 1H).
Reference: [1] Patent: CN106146401, 2016, A, . Location in patent: Paragraph 0117; 0190; 0191
[2] Patent: US2015/368278, 2015, A1, . Location in patent: Paragraph 1273; 1274
[3] Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 8166 - 8172
[4] Patent: US2007/173506, 2007, A1, . Location in patent: Page/Page column 48
[5] Organic Process Research and Development, 2011, vol. 15, # 3, p. 565 - 569
[6] Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 8166 - 8172
  • 2
  • [ 93777-26-5 ]
  • [ 79762-54-2 ]
YieldReaction ConditionsOperation in experiment
76% With hydrazine hydrate In dimethyl sulfoxide at 120℃; for 21 h; To a vigorously stirred solution of 5-bromo-2-fluorobenzaldehyde (40.6 g, 0.2 mol) in DMSO (80 mL) was added N2H4-xH2O (40 mL, 0.8 mol) dropwise over 15 min (slow addition to keep the reaction not too hot). The resulting yellow slurry was heated at 120 0C (oil temp.) for 21 h. The whole mixture was transferred to a 1 L flask and cooled for 10 min in air before quenching with ice (300 mL) and ice- cold H2O (100 mL). The resulting mixture was stirred for 30 min at it. Precipitated formed was collected by suction filtration, rinsed thoroughly with H2O (100 mL x 2), 2 M HCl (100 mL x 2), H2O (100 mL x 2), 0.5 M Na2CO3 (100 mL x 2), H2O (100 mL x 2), dried in air for 1 h and under high vacuum for 2 days to give 6- bromo-lH-indazole (30.05 g, 76percent) as a light yellow solid. MS ESI 196.9 [M + H]+, calcd for [C7H5BrN2 + H]+ 197.0.
Reference: [1] Patent: WO2009/79767, 2009, A1, . Location in patent: Page/Page column 84
  • 3
  • [ 6967-12-0 ]
  • [ 79762-54-2 ]
YieldReaction ConditionsOperation in experiment
48%
Stage #1: With hydrogen bromide; sodium nitrite In water at 0℃; for 0.25 h;
Stage #2: With copper(I) bromide In water at 20 - 80℃; for 1.5 h;
6-Aminoindazole (1.33 g, 10 mmol) was dissolved in 48percent hydrobromic acid (5 mL) and water (16 mL). To the resulting solution at 0° C. was added dropwise a solution of sodium nitrite (0.77 g, 11 mmol) in water (9 mL). The mixture was stirred at 0° C. for 15 min. Urea (0.40 g) was added to remove excess nitrous acid. After stirring for 10 min, this solution was added dropwise to a stirred mixture of copper(I) bromide (4.3 g, 30 mmol), 48percent hydrobromic acid (10 mL) and water (24 mL) at room temperature. The reaction mixture was heated at 75-80° C. for 1.5 h, cooled to room temperature, basified with concentrated ammonium hydroxide, and extracted with chloroform (4.x.30 mL). The combined extracts were dried over sodium sulfate and concentrated to provide the bromoindazole (0.96 g, 48percent) as a greenish yellow solid; 1H NMR (500 MHz, DMSO-d6) δ 13.16 (s, 1H), 8.09 (s, 1H), 7.67 (s, 1H), 7.74-7.72 (d, J=8.5 Hz, 1H), 7.25-7.23 (dd, J=8.5, 1.4 Hz, 1H).
Reference: [1] Patent: US2006/142307, 2006, A1, . Location in patent: Page/Page column 8
  • 4
  • [ 39478-78-9 ]
  • [ 79762-54-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 23, p. 6049 - 6053
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 10, p. 4458 - 4473
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3177 - 3180
[4] Patent: EP1622569, 2015, B1,
  • 5
  • [ 6967-12-0 ]
  • [ 12775-96-1 ]
  • [ 79762-54-2 ]
YieldReaction ConditionsOperation in experiment
16% With hydrogen bromide; sodium nitrite In hexane; water; ethyl acetate (i)
6-Bromo-1H-indazole
Sodium nitrite (315 mg, 4.56 mmol) was added in 2 portions to an ice-cooled suspension of 6-aminoindazole (500 mg, 3.8 mmol) in water (0.4 mL) and hydrobromic acid (48percent, 1.8 mL).
The reaction mixture was stirred for 10 minutes longer than required for the brown gas to disappear.
Copper powder (35 mg, 0.55 mmol) was then added and the mixture heated gently until nitrogen evolution began.
The reaction mixture was then alternately heated and cooled to control the rate of reaction.
When nitrogen evolution ceased, the reaction mixture was heated at 90° C. for 30 minutes, cooled to room temperature, neutralized with aqueous sodium hydroxide and the product extracted into ethyl acetate.
The organic layer was washed sequentially with water and brine, dried over sodium sulfate and the solvent removed in vacuo.
Flash chromatography on silica gel (20-40percent ethyl acetate in hexane) yield the title product (119 mg, 16percent).
Reference: [1] Patent: US6380242, 2002, B1,
  • 6
  • [ 593-56-6 ]
  • [ 57848-46-1 ]
  • [ 79762-54-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 19, p. 4143 - 4147
  • 7
  • [ 79762-54-2 ]
  • [ 74-88-4 ]
  • [ 590417-94-0 ]
YieldReaction ConditionsOperation in experiment
160 mg With potassium hydroxide In methanol for 2.5 h; Reflux [0411] 6-Bromoindazole (400 mg) was dissolved in methanol (10 mL). To this solution, potassium hydroxide (450 mg)was added followed by methyl iodide (0.50 mL) and the mixture was refluxed for 2.5 h. The reaction was cooled, dilutedwith diethyl ether, washed with water, brine, dried and concentrated. The product 6-bromo-1-methylindazole (160 mg)was separated from its isomer by Combiflash
Reference: [1] Patent: EP1622569, 2015, B1, . Location in patent: Paragraph 0411
[2] European Journal of Medicinal Chemistry, 2019, vol. 161, p. 533 - 542
  • 8
  • [ 79762-54-2 ]
  • [ 74-88-4 ]
  • [ 590417-94-0 ]
  • [ 590417-95-1 ]
Reference: [1] Patent: WO2015/42397, 2015, A1, . Location in patent: Paragraph 000898
[2] Patent: WO2015/65937, 2015, A1, . Location in patent: Paragraph 000807
  • 9
  • [ 79762-54-2 ]
  • [ 74-88-4 ]
  • [ 590417-94-0 ]
  • [ 590417-95-1 ]
Reference: [1] Patent: WO2015/42397, 2015, A1, . Location in patent: Paragraph 000898
[2] Patent: WO2015/65937, 2015, A1, . Location in patent: Paragraph 000807
  • 10
  • [ 79762-54-2 ]
  • [ 68-12-2 ]
  • [ 669050-69-5 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; for 1 h;
Stage #2: With sec.-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.25 h;
Stage #3: at 20℃;
To a suspension of 60 percent NaH (10.0 g, 0.24 mol) in THF (240 mL) was added a suspension of 6-bromo-lH-indazole (39.4 g, 0.2 mol) in THF (280 mL) dropwise over 45 min. After addition, the resulting mixture was stirred for 1 h at rt to give a dark red clear solution which was cooled to -78 0C.5-BuLi (1.4 M in <n="86"/>hexane, 300 mL, 0.42 mol) was added dropwsie over 1 h. During this addition, additional THF (130 mL) was added to keep the mixture stirring. After the addition, the resulting mixture was stirred for 75 min at -78 0C; DMF (90 mL) was added dropwise (note: reaction solidified upon addition of DMF, occasional warming was needed to keep the mixture stirring). The resulting mixture was stirred at it overnight and cooled to 0 0C. Solid NH4Cl and saturated NH4Cl were added to quench the reaction and bring the pH to about 7. The product was extracted with EtOAc (800 mL + 200 mL +300 mL, 1.3 L in total) and the combined extracts were washed with H2O (300 mL x 3) and dried (Na2SO4). Evaporation of the solvent gave a dark red solid which was triturated by EtOAc (4 times, the last filtrate was purified by flash chromatography) to give the title compound (16.96 g in total, 58percent) as yellow brown solid. 1H NMR (400 MHz, DMSO-d6) δ 13.62 (s, IH, NH), 10.12 (s, IH, CHO), 8.23 (s, IH), 8.17 (s, IH), 7.93 (d, J = 8.4 Hz, IH), 7.59 (d, J = 8.4 Hz, IH); MS ESI 147.0 [M + H]+, calcd for [C8H6N2O+ H]+ 147.0.
Reference: [1] Patent: WO2009/79767, 2009, A1, . Location in patent: Page/Page column 84-85
  • 11
  • [ 79762-54-2 ]
  • [ 24424-99-5 ]
  • [ 877264-77-2 ]
YieldReaction ConditionsOperation in experiment
94% With dmap; triethylamine In acetonitrile at 0 - 20℃; for 18 h; a) 1,1 -dimethylethyl 6-bromo- lH-indazole- 1 -carboxylateA suspension of 6-bromo-lH-indazole (82.74 mmol), DMAP (16.55 mmol), and Et3N (19.56 mL) in CH3CN at 0 °C was treated with bis( 1,1 -dimethylethyl) dicarbonate (82.74 mmol) in CH3CN over 15 min such that the internal temperature remained at 5 °C. The reaction mixture was warmed to room temperature and stirred for 18 h. The reaction was concentrated in vacuo and the residue purified by flash chromatography (7percentEtO Ac/petroleum ether) to afford the title compound (23.2 g, 94percent) as a solid.
94% With dmap; triethylamine In acetonitrile at 5 - 20℃; for 18.25 h; 1 ,1 -Dimethylethyl 6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-indazole-1 - carboxylate(a) 1 ,1 -Dimethylethyl 6-bromo-1 H-indazole-1 -carboxylateA suspension of 6-bromo-1 /-/-indazole (82.74 mmol), 4-(dimethylamino)pyridine (16.55 mmol), and triethylamine (19.56 ml.) in acetonitrile at 0 °C was treated with bis(1 , 1 - dimethylethyl) dicarbonate (82.74 mmol) in acetonitrile over 15 min such that the internal temperature remained at 5 °C. The reaction mixture was warmed to room temperature and stirred for 18 h. The reaction was concentrated in vacuo and the residue purified by flash chromatography (7percent ethyl acetate/petroleum ether) to afford the title product as a solid (23.2 g, 94percent).
63% With dmap; triethylamine In acetonitrile at 0 - 20℃; To a 0 °C solution of 6-bromo-lH-indazole (20 mmol), triethylamine (4 mL), and 4-(dimethylamino)pyridine (4 mmol) in acetonitrile (100 mL) was dropwise added bis( 1 , 1 -dimethylethyl) dicarbonate (20 mmol) in acetonitrile. The reaction mixture was then stirred at room temperature overnight. The mixture was concentrated in vacuo and the residue was purified by flash chromatography (10percent ethyl acetate/petroleum ether) to give the title product (63percent).
Reference: [1] Patent: WO2012/37298, 2012, A1, . Location in patent: Page/Page column 49
[2] Patent: WO2013/28445, 2013, A1, . Location in patent: Page/Page column 54; 55
[3] Patent: WO2011/66211, 2011, A1, . Location in patent: Page/Page column 71-72
[4] Patent: WO2016/57834, 2016, A1, . Location in patent: Paragraph 000198
  • 12
  • [ 79762-54-2 ]
  • [ 73183-34-3 ]
  • [ 937049-58-6 ]
YieldReaction ConditionsOperation in experiment
100% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 100℃; for 15 h; Inert atmosphere A mixture of 6-bromo-1 /-/-indazole (700 mg; 3.55 mmol), 4,4,4',4',5,5,5',5'-octamethyl- 2,2'-bi(1 ,3,2-dioxaborolane) (1 .50 g; 5.91 mmol), Pd(dppf)CI2- DCM (290 mg; 0.36 mmol) and KOAc (1 .04 g; 10.6 mmol) in DMF (20 mL) was stirred at 100°C for 15 hours under nitrogen. The mixture was concentrated in vacuo, suspended in EtOAc (30 mL), filtered through Celite, and concentrated to afford 866 mg (100percent) of the title compound as a brown semi-solid, which was used directly without further purification. LC-MS for Ci3H17BN2O2+H+ [M+H]+: calcd. 245.1 ; found: 245.0.
81% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 100℃; Sealed tube; Inert atmosphere A 6-bromo-lH-indazole (3.0 g, 15.2 mmol), bis(pinacolato)diboron (7.7 g, 30.4 mmol), potassium acetate (5.9 g, 60.9 mmol) in dry N,N-dimethylformamide (40 mL) were placed in a sealed tube under argon purge. The reaction mixture was degassed for a further 10 min with a slow stream of argon, at which point [ 1 , 1 '- bis(diphenylphosphino)ferrocene]palladium(II) chloride, complex with dichloromethane (0.3 g) was added. The reaction mixture was heated at 100°C overnight. After cooled to ambient temperature reaction mixture was filtered through Celite, washed with ethyl acetate and solvents were evaporated under reduced pressure. Crude product was purified by flash chromatography (silica gel; hexane/ethyl acetate 1 : 1) to give 6-(tetramethyl-l ,3,2-dioxaborolan-2-yl)-lH- indazole (3.0 g); yield 81percent. LC-MS (m/z) 244.9 (M+l).
Reference: [1] Patent: WO2015/140717, 2015, A1, . Location in patent: Page/Page column 87; 88
[2] Patent: WO2017/68064, 2017, A1, . Location in patent: Page/Page column 182
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 10, p. 4458 - 4473
[4] Patent: US2007/203143, 2007, A1, . Location in patent: Page/Page column 50
[5] RSC Advances, 2017, vol. 7, # 44, p. 27737 - 27746
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 79762-54-2 ]

Bromides

Chemical Structure| 186407-74-9

[ 186407-74-9 ]

4-Bromo-1H-indazole

Similarity: 0.97

Chemical Structure| 156454-43-2

[ 156454-43-2 ]

5-Bromo-7-methyl-1H-indazole

Similarity: 0.97

Chemical Structure| 885518-50-3

[ 885518-50-3 ]

6-Bromo-1H-indazol-4-amine

Similarity: 0.95

Chemical Structure| 926922-40-9

[ 926922-40-9 ]

4-Bromo-5-methyl-1H-indazole

Similarity: 0.94

Chemical Structure| 53857-58-2

[ 53857-58-2 ]

7-Bromo-1H-indazole

Similarity: 0.92

Related Parent Nucleus of
[ 79762-54-2 ]

Indazoles

Chemical Structure| 186407-74-9

[ 186407-74-9 ]

4-Bromo-1H-indazole

Similarity: 0.97

Chemical Structure| 156454-43-2

[ 156454-43-2 ]

5-Bromo-7-methyl-1H-indazole

Similarity: 0.97

Chemical Structure| 885518-50-3

[ 885518-50-3 ]

6-Bromo-1H-indazol-4-amine

Similarity: 0.95

Chemical Structure| 926922-40-9

[ 926922-40-9 ]

4-Bromo-5-methyl-1H-indazole

Similarity: 0.94

Chemical Structure| 53857-58-2

[ 53857-58-2 ]

7-Bromo-1H-indazole

Similarity: 0.92