Home Cart 0 Sign in  

[ CAS No. 1168135-03-2 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1168135-03-2
Chemical Structure| 1168135-03-2
Structure of 1168135-03-2 * Storage: {[proInfo.prStorage]}

Quality Control of [ 1168135-03-2 ]

Related Doc. of [ 1168135-03-2 ]

SDS
Alternatived Products of [ 1168135-03-2 ]
Alternatived Products of [ 1168135-03-2 ]

Product Details of [ 1168135-03-2 ]

CAS No. :1168135-03-2 MDL No. :MFCD11867874
Formula : C12H15BN2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :262.14 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1168135-03-2 ]

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 [ 1168135-03-2 ]

  • Downstream synthetic route of [ 1168135-03-2 ]

[ 1168135-03-2 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 1168135-03-2 ]
  • [ 1168133-92-3 ]
  • [ 1168133-94-5 ]
YieldReaction ConditionsOperation in experiment
50% With cesium fluoride In 1,2-dimethoxyethane at 100℃; for 18h; Inert atmosphere; 2995.1 Example 2995: 2-(4-Benzo[l,2,5]thiadiazol-5-yl-3-chloro-5-cyclopropylmethoxy- phenyl)-4-methyl-pentanoic acid Step l2-(4-Benzo[l,2,5]thiadiazol-5-yl-3-chloro-5-cyclopropylmethoxy-phenyl)-4-methyl- pentanoic acid cyclopropylmethyl esterTo a solution of 2-(3-chloro-5-cyclopropylmethoxy-4-iodo-phenyl)-4-methyl-pentanoic acid cyclopropylmethyl ester (0.18 g, 0.38 mmol) in DME (anhydrous, 10 mL) under argon atmosphere were added 5-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)- benzo[l,2,5]thiodiazole (0.15 g, 0.57 mmol), CsF (0.14 g, 0.92 mmol), and [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.02 g, 0.027 mmol). The reaction mixture was refluxed for 18 h (oil bath, 1000C). A mixture of water and EtOAc (15 mL/15 mL) was added and the layers were separated. The combined organic phases were dried over MgS O4 and evaporated to give a crude yellow oil, which was purified by silica gel gradient column chromatography by use of Heptane-EtOAc (20: 1 - 9:1) to give 2-(4-benzo[l,2,5]thiadiazol-5-yl-3-chloro-5-cyclopropylmethoxy-phenyl)-4-methyl- pentanoic acid cyclopropylmethyl ester (0.08 g, 50%) as a yellow oil. 1H NMR (300 MHz, CDCI3/TMS): δ 7.83 (d, J = 9.3 Hz, IH), 7.77 (s, IH), 7.36-7.33 (m, IH), 7.11 (s, IH), 6.91 (s, IH), 4.02-3.81 (m, 4H), 3.67 (t, J = 7.7 Hz, IH), 2.03-1.96 (m, IH), 1.74- 1.65 (m, IH), 1.60-1.45 (m, IH), 1.20-1.05 (m, 2H), 0.96 (d, J= 6.3 Hz, 6H), 0.57-0.47 (m, 4H), 0.28 (br s, 2H), 0.19 (br s, 2H). 13C NMR (75 MHz, CDC13/TMS): δ 173.5, 157.1, 154.7, 154.0, 141.4, 136.8, 133.7, 132.9, 126.9, 122.8, 121.6, 120.0, 110.8, 73.3, 69.7, 49.7, 42.7, 26.1, 22.5, 22.5, 10.0, 9.8, 3.3, 3.1
50% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 1,2-dimethoxyethane at 100℃; for 18h; Inert atmosphere; 2995.1 Step 12-(4-Benzo[l ,2,5]tb"adiazol~5-yl-3-cWoro-5-cyclopropylmethpentanoic acid cyclopropylm ethyl ester To a solution of 2-(3-chloro-5-cyclopropylmethoxy-4-iodo-phenyl)-4-methyl- pentanoic acid cyclopropylmethyl ester (0.18 g, 0.38 mmol) in DME (anhydrous, 10 mL) under argon atmosphere were added 5-(4,4,5,5-tetramethyl-[l,3,2]dioxa.borolan-2-yi)- benzo[l,2,5]thiodiazole (0, 15 g, 0.57 mmol), CsF (0.14 g, 0.92 mmol), and [1 ,1'- bis(diphenylphosphino)ferrocene]dichloropalladium. (II) (0.02 g, 0.027 mmol). The reaction mixture was refiuxed for 1 8 h (oil bath, 100°C). A mixture of water and EtOAc (15 mL/15 mL) was added and the layers were separated. The combined organic phases were dried over MgS04and evaporated to give a crude yellow oil, which was purified by silica gel gradient column chromatography by use of Heptane-EtO Ac (20: 1 - 9: 1) to give 2-(4-benzo[l,2,5]thiadiazol-5-yl-3-chloro-5-cyclopropylmethoxy-phenyl)-4-methyl- pentanoic acid cyclopropylmethyl ester (0.08 g, 50%) as a yellow oil. 1H MR (300MHz, CDCI3/TMS): δ 7.83 (d, J = 9.3 Hz, 1H), 7.77 (s, 1H), 7.36-7.33 (m, 1H), 7.11 (s, I I I). 6.91 (s, H i). 4.02-3.81 (m, 4H), 3.67 (t, ,/ 7.7 Hz, f ). 2.03-1.96 (m, I f ). 1.74- 1.65 (m, i l l ). 1.60-1.45 (m, IH), 1.20-1.05 (m, 2H), 0.96 (d . ./ 6.3 Hz, 61 1). 0.57-0.47 (m, 4H), 0.28 (br s, 2H), 0.19 (br s, 21 }.i3C NMR (75 MHz, CDCI3/TMS): δ 173.5, 157.1, 154.7, 154.0, 141.4, 136.8, 133.7, 132.9, 126.9, 122.8, 121.6, 120.0, 110.8, 73.3, 69.7, 49.7, 42.7, 26.1 , 22.5, 22.5, 10.0, 9.8, 3.3, 3.1.
  • 2
  • [ 1168135-03-2 ]
  • [ 1168134-90-4 ]
  • [ 1168134-93-7 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In water; N,N-dimethyl-formamide at 20 - 80℃; for 14h; 524.1 Example 524 : 2-(3-(benzo[c][l,2,5]thiadiazol-5-yl)-5-chloro-4-(cyclopropylmethoxy)phenyl)-4-methylpentanoic acidStep lEthyl 2-(3-(benzo[c][l,2,5]thiadiazol-5-yl)-5-chloro-4-(cyclopropylmethoxy)phenyl)-4-methylpentanoate To a stirred solution of ethyl 2-(3-bromo-5-chloro-4-(cyclopropylmethoxy)phenyl)-4- methylpentanoate (0.5 g, 1.239 mmol) in a mixture of DMF (10 mL) and water (5 mL) were added Cs2CO3 (1.4 g, 4.325 mmol), Pd(TPP) 4 (286 mg, 2.475 mmol) and 5- (4,4,5,5,-tetramethyl-l,3,2-dioxaborolan-2yl)benzo[c][l,2,5]thiazdiazole (355 mg, 1.363 mmol) at RT under N2 atmosphere and the resulting mixture was stirred at 80 C for 14 h. After completion of starting material (by TLC), the solids were removed via filtration through a bed of Celite was washing with EtOAc (3 x 100 mL). The combined organic layers were washed with water (3 x 50 mL), brine and dried over anhydrous Na2SO^ filtered and concentrated under reduced pressure. The crude material was purified by column chromatography to afford ethyl 2-(3-(benzo[c][l,2,5]thiadiazol-5-yl)-5-chloro-4- (cyclopropylmethoxy)phenyl)-4-methylpentanoate (222 mg) as an off white solid.
222 mg With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In water; N,N-dimethyl-formamide at 80℃; for 14h; Inert atmosphere; 524.1 Ethyl 2-(3-(benzo[c][ 1 ,2,5] thiadiazol-5-yl)-5-c oro-4-(cyclopropylmethoxy)phenyl)- 4-methylpentanoate To a stirred solution of ethyl 2-(3-bromo-5-chloro-4-(cyclopropylmethoxy)phenyl)-4- methylpentanoate (0.5 g, 1.239 mmol) in a mixture of DMF (10 mL) and water (5 mL) were added Cs2C03(1.4 g, 4.325 mmol), Pd(TPP)4(286 mg, 2.475 mmol) and 5- (4,4,5,5, -tetramethyl-1 , 3,2-dioxaborolan- 2yl)benzo[c][l ,2,5Jthiazdiazole (355 mg, 1.363 mmol) at RT under N2 atmosphere and the resulting mixture was stirred at 80 °C for 14 h. After completion of starting material (by TLC), the solids were removed via filtration through a bed of Ceiite was washing with EtOAc (3 x 100 mL). The combined organic layers were washed with water (3 x 50 mL), brine and dried over anhydrous NaaSO^ filtered and concentrated under reduced pressure. The cmde material was purified by column chromatography to afford ethyl 2- (3-(benzo[c][l,2,5]fhiadiazol-5-yl)-5-chloro-4- (cyclopropylmethoxy)phenyl)-4- methylpentanoate (222 mg) as an off white solid.
  • 3
  • [ 1753-75-9 ]
  • [ 1168135-03-2 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate; In N,N-dimethyl-formamide; Preparation 44 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole Dichloro[1,1'-bis(diphenylphosphino)ferrocene]-palladium(II) (100 mg, 0.14 mmol, 0.03), potassium acetate (1.4 g, 14 mmol), and diboron bis(pinocol) ester (1.2 g, 4.7 mmol) were sequentially added to a stirred solution of <strong>[1753-75-9]5-bromobenzo[c][1,2,5]thiadiazole</strong> (1.0 g, 4.7 mmol) in N,N-dimethylformamide (12 mL) at 23 C. The resulting dark brown mixture was sealed under nitrogen, heated to 80 C., and stirred for 24 h. The cooled reaction mixture was diluted with water (500 mL) and extracted with diethyl ether (4*100 mL). The combined organic layers were diluted with hexane (100 mL) and washed with water (1*200 mL). The organic layer was dried (magnesium sulfate), gravity filtered, and concentrated by rotary evaporation to afford the title compound as a brown powder (960 mg, 80% yield): IR (KBr thin film) 2977 (m), 2930 (w), 1607 (w), 1471 (m) cm-1; 1H NMR (400 MHz, CDCl3) delta 8.54 (s, 1H), 7.93-8.01 (m, 2H), 1.40 (s, 12H).
  • 4
  • [ 1168135-03-2 ]
  • [ 4316-58-9 ]
  • 4-(benzo[c][1,2,5]thiadiazol-5-yl)-N,N-bis(4-bromophenyl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 80℃; for 24h; Inert atmosphere; Schlenk technique;
  • 5
  • [ 1168135-03-2 ]
  • [ 4316-58-9 ]
  • 4-(benzo[c][1,2,5]thiadiazol-5-yl)-N,N-bis(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / 24 h / 80 °C / Inert atmosphere; Schlenk technique 2: 1,10-Phenanthroline; caesium carbonate; copper(l) iodide / N,N-dimethyl-formamide / Reflux; Inert atmosphere; Schlenk technique
  • 6
  • [ 1168135-03-2 ]
  • 4-bromo-N-(4-bromophenyl)-N-(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)aniline [ No CAS ]
  • 4-(benzo[c][1,2,5]thiadiazol-5-yl)-N-(4-(benzo[c][1,2,5]thiadiazol-5-yl)phenyl)-N-(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 80℃; for 24h; Inert atmosphere; Schlenk technique;
  • 7
  • [ 1753-75-9 ]
  • [ 61676-62-8 ]
  • [ 1168135-03-2 ]
  • 8
  • [ 1575-37-7 ]
  • [ 1168135-03-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: thionyl chloride; pyridine / 5 h / 0 °C / Reflux; Inert atmosphere; Schlenk technique 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: -78 - 20 °C / Inert atmosphere; Schlenk technique
  • 9
  • [ 1168135-03-2 ]
  • 8-chloro-N-(4-methanesulfonylpyridin-3-yl)quinoxalin-6-amine [ No CAS ]
  • 8-(2,1,3-benzothiadiazol-5-yl)-N-(4-methanesulfonylpyridin-3-yl)quinoxalin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 140℃; for 1.5h; Microwave irradiation; 117 Example 1 17 8-(2,1 ,3-Benzothiadiazol-5-yl)-A/-(4-methanesulfonylpyridin-3-yl)quinoxalin-6- amine The title compound is prepared according to General Procedure 15 described in Example 60, using 5-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)- benzo[1 ,2,5]thiadiazole (30 mg; 0.12 mmol; 1.20 eq.), 8-chloro-/V-(4- methanesulfonylpyridin-3-yl)quinoxalin-6-amine (Intermediate 3B, 33 mg; 0.10 mmol; 1 eq.), sodium carbonate (15 mg; 0.15 mmol; 1.50 eq.), tetrakis(triphenylphosphine)palladium(0) (1 1 mg, 0.01 mmol, 0.1 eq.) in dioxane (1.3 mL) and water (1.3 mL). Conditions: 140 °C under microwave irradiation for 90 min. Purification by reversed-phase preparative HPLC (column: Gemini NX C18 5u 1 10A (100x30 mm), ACN gradient in water) yielded 8-(2, 1 ,3-benzothiadiazol-5-yl)-A/-(4-methanesulfonylpyridin-3- yl)quinoxalin-6-amine formate salt (5 mg, 0.01 mmol, 11 %; yellow powder; HPLC purity: 100%).
  • 10
  • [ 64-18-6 ]
  • [ 1168135-03-2 ]
  • 8-chloro-N-(4-methanesulfonylpyridin-3-yl)quinoxalin-6-amine [ No CAS ]
  • 8-(2,1,3-benzothiadiazol-5-yl)-N-(4-methanesulfonylpyridin-3-yl)quinoxalin-6-amine formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% Stage #1: 5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzo[c][1,2,5]thiodiazole; 8-chloro-N-(4-methanesulfonylpyridin-3-yl)quinoxalin-6-amine With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 140℃; for 1.5h; Inert atmosphere; Microwave irradiation; Stage #2: formic acid In water; acetonitrile
  • 11
  • [ 1168135-03-2 ]
  • [ 74-88-4 ]
  • [ 1457-93-8 ]
YieldReaction ConditionsOperation in experiment
92% With C21H30ClNPPd; potassium <i>tert</i>-butylate In tert-Amyl alcohol at 65℃; for 18h; Sealed tube; Inert atmosphere; Glovebox;
  • 12
  • [ 1168135-03-2 ]
  • 4,9-dibromo-6,7-bis(4-(2-(2-ethoxylethoxy)ethoxy)phenyl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline [ No CAS ]
  • C44H40N8O6S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tris-(dibenzylideneacetone)dipalladium(0); tetraethylammonium hydroxide; tris-(o-tolyl)phosphine In water; toluene at 90℃; for 12h; Inert atmosphere; Schlenk technique;
  • 13
  • [ 1753-75-9 ]
  • [ 73183-34-3 ]
  • [ 1168135-03-2 ]
  • 14
  • [ 1168135-03-2 ]
  • [ 768-10-5 ]
YieldReaction ConditionsOperation in experiment
52.0 mg With water; dihydrogen peroxide; sodium hydroxide In dichloromethane at 0 - 25℃; for 6h; Inert atmosphere;
  • 15
  • [ 15854-87-2 ]
  • [ 1168135-03-2 ]
  • 5-(4-pyridyl)-2,1,3-benzothiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 120℃; for 0.5h; Inert atmosphere; Microwave irradiation; 6 Example 6: Preparation of 5-(4-pyridyl)-2,1 ,3-benzothiadiazole A microwave vial was charged, under nitrogen atmosphere, with 4-iodopyridine (0.1 g), 5-(4, 4,5,5- tetramethyl-1 ,3, 2-dioxaborolan-2-yl)-2,1 ,3-benzothiadiazole (0.141 g), 1 ,1'- bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (0.04 g), cesium carbonate (0.239 g), 1 ,4-dioxane (0.805 mL) and water (0.268 mL). The mixture was heated at 120°C under microwave irradiation for 30 minutes. The reaction mixture was diluted with dichloromethane, filtered through a pad of celite, which was washed with further dichloromethane. The filtrate was concentrated and purified by silica gel chromatography eluting with a mixture of ethyl acetate and hexanes to give 5-(4-pyridyl)-2,1 ,3-benzothiadiazole as an off-white solid. 1H NMR (400 MHz, CDCl3) 8.77 (br s, 2H), 8.28 (dd, 1 H), 8.14 (dd, 1 H), 7.89 (dd, 1 H), 7.63 (d, 2H)
  • 16
  • [ 1168135-03-2 ]
  • 2,2’’,6,6’’-tetrabromo-4,4’’-di-tert-butyl-1,1’:4’,1’’-terphenyl [ No CAS ]
  • 5,5',5'',5'''-(4,4''-di-tert-butyl-[1,1':4',1''-terphenyl]-2,2'',6,6''-tetrayl)tetrakis(benzo[c][1,2,5]thiadiazole) [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 24h; Inert atmosphere;
Historical Records

Related Functional Groups of
[ 1168135-03-2 ]

Organoboron

Chemical Structure| 1088118-97-1

[ 1088118-97-1 ]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole

Similarity: 0.92

Esters

Chemical Structure| 934365-16-9

[ 934365-16-9 ]

4,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole

Similarity: 0.92

Chemical Structure| 1088118-97-1

[ 1088118-97-1 ]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole

Similarity: 0.92

Chemical Structure| 1467776-41-5

[ 1467776-41-5 ]

5,10-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphtho[1,2-c:5,6-c']bis([1,2,5]thiadiazole)

Similarity: 0.88

Related Parent Nucleus of
[ 1168135-03-2 ]

Other Aromatic Heterocycles

Chemical Structure| 1088118-97-1

[ 1088118-97-1 ]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[c][1,2,5]thiadiazole

Similarity: 0.92