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[ CAS No. 1000994-94-4 ] {[proInfo.proName]}

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Chemical Structure| 1000994-94-4
Chemical Structure| 1000994-94-4
Structure of 1000994-94-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1000994-94-4 ]

CAS No. :1000994-94-4 MDL No. :MFCD13186728
Formula : C14H19BF2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZEIACFZGYHZGTL-UHFFFAOYSA-N
M.W : 268.11 Pubchem ID :46835487
Synonyms :

Calculated chemistry of [ 1000994-94-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.57
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 72.68
TPSA : 18.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.72
Log Po/w (WLOGP) : 3.83
Log Po/w (MLOGP) : 2.8
Log Po/w (SILICOS-IT) : 2.95
Consensus Log Po/w : 2.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.95
Solubility : 0.0303 mg/ml ; 0.000113 mol/l
Class : Soluble
Log S (Ali) : -3.8
Solubility : 0.0426 mg/ml ; 0.000159 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.99
Solubility : 0.00273 mg/ml ; 0.0000102 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.86

Safety of [ 1000994-94-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501 UN#:1759
Hazard Statements:H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1000994-94-4 ]

* 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 [ 1000994-94-4 ]

[ 1000994-94-4 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 1000994-95-5 ]
  • [ 73183-34-3 ]
  • [ 1000994-94-4 ]
YieldReaction ConditionsOperation in experiment
66% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90℃; for 10h; Bispinacol diborate (22.5 g), [1,1?-bis(diphenylphosphino)ferrocene]palladium(II) dichloride-dichloromethanecomplex (904 mg) and potassium acetate (8.70 g) were added to a solution of <strong>[1000994-95-5]1-bromo-4-(1,1-difluoroethyl)benzene</strong>(9.80 g) synthesized in Example 1-(1) in 1,4-dioxane (60 mL), and stirred at 90C for 10 hours. The reaction solutionwas poured into water, followed by extraction with chloroform. The solvent was evaporated under reduced pressure andthe obtained residue was purified by silica gel column chromatography (hexane) to give the title compound (7.87 g, yield66%) as a colorless solid.1H NMR (600 MHz, CDCl3) delta ppm 1.35 (s, 12H), 1.91 (t, J=18.2 Hz, 3H), 7.50 (d, J=7.8 Hz, 2H), 7.86 (d, J=7.8 Hz, 2H).
38% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 8h; In a 40 ml vial, bromo derivative (250 mg, 1.13 mmol, 1.0 eq.), bispinacolotodiboron (288.6 mg, 1.13 mmol, 1.0 eq.), Pd(dppf)CI2 (92.7 mg, 0.114 mmol, 0.1 eq.) and potassium acetate (354.5 mg, 3.41 mmol, 3.0 eq.) were mixed in dioxane (10 ml) and heated to 80 C for 8 hours. LCMS indicated that the product was formed in major amount. . The crude reaction was purified in the presence of silica (10-15 gm) and purified using hexanes: ethyl acetate (0-100%) to yield desired boron ester. The product was characterized by reverse phase HPLC using method 4. (ES, m/z) [M + H+] 269.0. Retention time = 1.60 mins.
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 80℃; Step 4:To a mixture of compound 5b4 (210 mg, 0.95 mmol) in DMF (6.0 mL) is added bis(pinacolato)diboron (265 mg, 1.045 mmol) and KOAc (205 mg, 2.09 mmol). Argon is passed through the mixture for 5 minutes and PdCI2(dppf)-CH2CI2 (77.6 mg, 0.095 mmol) is added. Argon is passed through the mixture for 3 minutes further and the mixture is allowed to react at 80C overnight. The mixture is extracted with EtOAc and the extract is washed with brine, dried (MgSO4), filtered through Celite and concentrated to provide boronic acid 5b5.
  • 2
  • [ 1000994-94-4 ]
  • C17H19ClINO3 [ No CAS ]
  • C24H23ClF3NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.166667h; Microwave irradiation; 5B.5 Step 5: A mixture of compound 5b3 (90 mg, 0.208 mmol), compound 5b5 (11 1.3 mg, 0.415 mmol), K2CO3 (86 mg, 0.623 mmol), Pd(PPh3)4 (24.0 mg, 0.021 mmol) and DMF (6.0 mL) is allowed to react in a Biotage Initiator Sixty microwave apparatus at 120°C for two periods of 5 minutes each. The reaction mixture is diluted with EtOAc, washed with brine, dried (MgSO4), filtered and concentrated. The residue is purified by flash chromatography to provide compound 5b6.
  • 3
  • [ 1899-24-7 ]
  • [ 1000994-94-4 ]
  • {cis-5-[4-(1,1-difluoroethyl)phenyl]tetrahydrofuran-2-yl}methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ruthenium(IV) oxide hydrate 36 Step 3. 36. The requisite {cis-5-[4-(1,1-difluoroethyl)phenyl]tetrahydrofuran-2-yl}methanol was prepared via Suzuki reaction of 5-bromofuran-2-carbaldehyde with 2-[4-(1,1-difluoroethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, followed by hydrogenation in the presence of ruthenium(IV) oxide hydrate.
  • 4
  • [ 1000994-94-4 ]
  • 3-cyclopropyl-6-[(1R)-1-[4-(1,1-difluoroethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethyl]-1,2-dihydropyridin-2-one [ No CAS ]
  • C22H24F2N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate; trifuran-2-yl-phosphane; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C / Inert atmosphere 3: chloro-trimethyl-silane; potassium iodide / acetonitrile / 1 h / 60 °C 4: CHIRALPAK IB 4.6 x 250 mm 5 mm (DAICEL) / hexane; ethanol / Resolution of racemate
  • 5
  • [ 1000994-94-4 ]
  • (5R)-5-{2-(5-cyclopropyl-6-methoxypyridin-2-yl)-2-[4-(1,1-difluoroethyl)phenyl]ethyl}pyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate; trifuran-2-yl-phosphane; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C / Inert atmosphere
  • 6
  • [ 1000994-94-4 ]
  • 3-cyclopropyl-6-{1-[4-(1,1-difluoroethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethyl}pyridin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate; trifuran-2-yl-phosphane; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C / Inert atmosphere 3: chloro-trimethyl-silane; potassium iodide / acetonitrile / 1 h / 60 °C
  • 7
  • [ 1000994-94-4 ]
  • (5R)-5-{(Z)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)-2-[4-(1,1-difluoroethyl)phenyl]ethenyl}pyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: caesium carbonate; trifuran-2-yl-phosphane; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 20 °C / Inert atmosphere 3: chloro-trimethyl-silane; potassium iodide / acetonitrile / 1 h / 60 °C 4: CHIRALPAK IB 4.6 x 250 mm 5 mm (DAICEL) / hexane; ethanol / Resolution of racemate 5: lithium hexamethyldisilazane / tetrahydrofuran; dichloromethane / 4.67 h / -78 °C / Inert atmosphere
  • 8
  • [ 1000994-94-4 ]
  • [ 1310949-41-7 ]
  • (5R)-5-{(E)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)-2-[4-(1,1-difluoroethyl)phenyl]ethenyl}pyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; caesium carbonate In 1,4-dioxane; water at 90℃; for 2h; Inert atmosphere; 1.6 (5R)-5-{(E)-2-(5-Cyclopropyl-6-methoxypyridin-2-yl)-2-[4-(1,1-difluoroethyl)phenyl]ethenyl}pyrrolidin-2-one In a nitrogen atmosphere, 2-[4-(1,1-difluoroethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.59 g) synthesizedin Example 1-(2), cesium carbonate (1.92 g), tris(dibenzylideneacetone)dipalladium (0) (271 mg), tri(2-furyl)phosphine (412 mg) and distilled water (10 mL) were added to a solution of (5R)-5-[(Z)-2-bromo-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one (1.0 g) synthesized in Example 1-(5) in 1,4-dioxane (50 mL), and the mixturewas stirred at 90°C for 2 hours. The reaction solution was poured into water, followed by extraction with ethyl acetate.The organic layer was dried over anhydrous magnesium sulfate, followed by separating the desiccant by filtration, andevaporating the solvent under reduced pressure. The obtained residue was purified by silica gel column chromatography(hexane:ethyl acetate = 100:0 → 0:100), further by NH silica gel column chromatography (hexane:ethyl acetate = 100:0→ 0:100) to give the title compound (1.13 g, yield 96%) as a colorless amorphous.1H NMR (600 MHz, CDCl3) δ ppm 0.56-0.64 (m, 2H), 0.90-0.97 (m, 2H), 1.93-2.09 (m, 5H), 2.20-2.34 (m, 2H), 2.37-2.45(m, 1H), 4.04 (s, 3H), 4.07-4.16 (m, 1H), 5.73-5.75 (br.s., 1H), 6.23 (d, J=7.4 Hz, 1H), 6.90 (d, J=9.9 Hz, 1H), 6.92 (d,J=7.8 Hz, 1H), 7.24 (d, J=8.3 Hz, 2H), 7.57 (d, J=7.8 Hz, 2H).MS (+): 399[M+H]+ .
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 2h; Inert atmosphere; Microwave irradiation; 21.B Step A: Preparation of 2-(2-fluoro-4-(trifluoromethoxy)phenyl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane. General procedure: Step A: Preparation of 2-(2-fluoro-4-(trifluoromethoxy)phenyl)-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane. To a microwave vial equipped with a magnetic stir bar were added 4,4,4',4',5,5,5',5'-octamethyl- 2,2'-bi(l,3,2-dioxaborolane) (294 mg, 1.16 mmol), potassium acetate (KOAc; 189 mg, 1.93 mmol) and Pd(dppf)Ci2 (70.6 mg, 0.097 mmol) and the vial was purged with N2. The resulting mixture was treated with a solution of l-bromo-2-fluoro-4-(trifluoromethoxy)benzene (250 mg, 0.96 mmol) in 1,4-dioxane (3.9 mL). The reaction vessel was capped, placed in a Biotage Initiator microwave reactor for 2 h at 100 °C, with external IR-sensor temperature monitoring from the side of the vessel. The cooled reaction mixture was filtered through a pad of Celite rinsing with EtOAc, and the filtrate was washed with sat'd aq NaHC03 (15 mL) and brine (2 x 15 mL). The organic phase was dried over MgS04, filtered, and concentrated to a brown oil which was used without further purification: 1H NMR (400 MHz, CDC13) δ 7.77 (dd, J= 8.3, 6.8 Hz, 1H), 7.01 (ddd, J= 8.3, 2.3, 1.1 Hz, 1H), 6.92 (ddd, J= 9.6, 2.2, 1.0 Hz, 1H), 1.36 (s, 12H); EIMS mlz 306.
  • 10
  • [ 1000994-94-4 ]
  • C17H19ClINO3 [ No CAS ]
  • C23H22ClF2NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.17 h / 120 °C / Microwave irradiation 2: methanol; lithium hydroxide; water / tetrahydrofuran / 2 h / 40 °C
  • 11
  • [ 1000994-94-4 ]
  • 7’-(2,6-difluoro-4-bromophenyl)spiro[cyclopropane-1,5’-imidazo[1,2-a]imidazole]-6’-one [ No CAS ]
  • 1'-(4'-(1,1-difluoroethyl)-3,5-difluoro-[1,1'-biphenyl]-4-yl)spiro[cyclopropane-1,3'-imidazo[1,2-a]imidazol]-2'(1'H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
64.8% With palladium diacetate; sodium carbonate; triphenylphosphine In water; N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere; 6 Preparation of 1'-(4'-(1,1-difluoroethyl)-3,5-difluoro-[1,1,-biphenyl]-4- yl)spiro[cyclopropane- 1 3 '-imidazo [ 1 ,2-a] imidazol] -2 '(1 'H)-one To a solution of -(4-bromo-2,6-difluorophenyl)spiro[cyclopropane-l,3'-imidazo[l,2- a]imidazol]-2'(l'H)-one (Example A.4) (20 mg, 58.8 μπιο, 1 eq.) in DME (200 μ) and water (50 μ) was added 2-(4-(l,l-difluoroethyl)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (23.6 mg, 88.2 μιηο, 1.5 eq.), triphenylphosphine (6.17 mg, 23.5 μιηο, 0.4 eq.), Na2C03 (31.2 mg, 294 μιηο, 5 eq.) and Pd(OAc)2 (2.64 mg, 11.8 μιηο, 0.2 eq.) under argon at room temperature. The mixture was stirred for 1 hr at 70 °C. The reaction mixture was diluted with saturated aqueous NaHC03-solution and extracted twice with EtOAc. The combined organic layers were washed with brine, dried over Na2S04 and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel (0% to 100% EtOAc in heptane). The desired Γ-(4'-(1,1- difluoroethyl)-3,5-difluoro-[l , l'-biphenyl]-4-yl)spiro[cyclopropane-1,3'-imidazo[l ,2-a]imidazol]-2'(1'H)-one (17 mg, 38.1 μιηο, 64.8 % yield) was obtained as a off-white semisolid. M+H+=402.2.
  • 12
  • [ 1000994-94-4 ]
  • 5-amino-7-chloro-2,3-dihydrobenzofuran-4-carbonitrile [ No CAS ]
  • 5-amino-7-(4-(1,1-difluoroethyl)phenyl)-2,3-dihydrobenzofuran-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium acetate; XPhos In 1,4-dioxane at 80℃; for 4h; Inert atmosphere; 48.1 Step 1: 5-amino-7-(4-(1,1-difluoroethyl)phenyl)-2,3-dihydrobenzofuran-4- carbonitrile To a solution of 5-amino-7-chloro-2,3-dihydrobenzofuran-4-carbonitrile (500 mg, 2.6 mmol) in 1,4-dioxane (5 mL) was added Potassium Acetate (504 mg, 5.2 mmol), Xphos Pd G2 (202 mg, 0.26 mmol), Xphos (122 mg, 0.26 mmol) and 2-(4-(1,1-difluoroethyl)phenyl)- 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1033 mg, 3.9 mmol). The resulting mixture was stirred at 80°C under N2 atmosphere for 4 hours. The mixture was diluted with water (20 mL) and extracted with EtOAc (10 mL × 3). The combined organic layers were dried over Na2SO4 and concentrated under vacuum. The residue was purified by chromatography on silica (0-10% EtOAc in petroleum ether) to afford the title compound (300 mg, 39%) as a yellow solid.1H NMR (400 MHz, CDCl3): δ 7.71 (d, J = 8.4 Hz, 2H), 7.57 (d, J = 8.4 Hz, 2H), 6.69 (s, 1H), 4.66 (t, J = 8.8 Hz, 2H), 4.12 (s, 2H), 3.38 (t, J = 8.8 Hz, 2H), 1.95 (t, J = 18.4 Hz, 3H); LCMS (ESI): m/z 301.1 (M+H)+.
  • 13
  • [ 99-90-1 ]
  • [ 1000994-94-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen fluoride; sulfur tetrafluoride / 4 h / 20 °C / Autoclave 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 12 h / 95 °C / Inert atmosphere
  • 14
  • [ 1000994-94-4 ]
  • 7-bromo-2,3-dihydrobenzofuran-5-amine [ No CAS ]
  • 7-(4-(1,1-difluoroethyl)phenyl)-2,3-dihydrobenzofuran-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; 18.1 Step 1: Preparation of 7-(4-(1,1-difluoroethyl)phenyl)-2,3-dihydrobenzofuran-5- amine A mixture of 7-bromo-2,3-dihydrobenzofuran-5-amine (5.0 g, 23.36 mmol), 2-(4- (1,1-difluoroethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.51 g, 28.03 mmol), Na2CO3 (7.43 g, 70.07 mmol), Pd(dppf)Cl2 (1.71 g, 2.34 mmol) in 1,4-Dioxane (52 mL) was stirred at 100°C for 16 hours under a N2atmosphere. The solution was then concentrated and the residue was purified by column chromatography on silica gel (0 - 30% EtOAc in petroleum ether) to afford the title compound (4.0 g, 62%) as a yellowish solid.1H NMR (400 MHz, CDCl3): δ 7.73 (d, J = 8.0 Hz, 2H), 7.55 (d, J = 8.0 Hz, 2H), 6.66 - 6.60 (m, 2H), 4.56 (t, J = 8.4 Hz, 2H), 3.47 (s, 2H), 3.18 (t, J = 8.4 Hz, 2H), 1.94 (t, J = 18.4, 3H); LCMS (ESI): m/z 276.11 (M+H)+.
62% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; 18.1 Step 1: Preparation of 7-(4-(1,1-difluoroethyl)phenyl)-2,3-dihydrobenzofuran-5- amine A mixture of 7-bromo-2,3-dihydrobenzofuran-5-amine (5.0 g, 23.36 mmol), 2-(4- (1,1-difluoroethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.51 g, 28.03 mmol), Na2CO3 (7.43 g, 70.07 mmol), Pd(dppf)Cl2 (1.71 g, 2.34 mmol) in 1,4-Dioxane (52 mL) was stirred at 100°C for 16 hours under a N2atmosphere. The solution was then concentrated and the residue was purified by column chromatography on silica gel (0 - 30% EtOAc in petroleum ether) to afford the title compound (4.0 g, 62%) as a yellowish solid.1H NMR (400 MHz, CDCl3): δ 7.73 (d, J = 8.0 Hz, 2H), 7.55 (d, J = 8.0 Hz, 2H), 6.66 - 6.60 (m, 2H), 4.56 (t, J = 8.4 Hz, 2H), 3.47 (s, 2H), 3.18 (t, J = 8.4 Hz, 2H), 1.94 (t, J = 18.4, 3H); LCMS (ESI): m/z 276.11 (M+H)+.
  • 15
  • [ 1000994-94-4 ]
  • 4-bromo-6-nitrobenzo[d]thiazole [ No CAS ]
  • 4-(4-(1,1-difluoroethyl)phenyl)-6-nitrobenzo[d]thiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere; 23.2 Step 2: Preparation of 4-(4-(1,1-Difluoroethyl)phenyl)-6-nitrobenzo[d]thiazole A mixture of 4-bromo-6-nitrobenzo[d]thiazole (5.0 g, 19.3 mmol), 2-(4-(1,1- difluoroethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (6.21 g, 23.16 mmol), Pd(dppf)Cl2 (1.41 g, 1.93 mmol), K2CO3 (8.0 g, 57.9 mmol) in 1,4-dioxane (50 mL) and water (5 mL) was stirred at 100°C for 2 hours under a N2atmosphere. The reaction mixture was concentrated under vacuum. The residue was purified by flash chromatography on silica gel (0 - 25% ethyl acetate in petroleum ether) to afford the title compound (5.5 g, 89%) as a yellow solid.
89% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere; 23.2 Step 2: Preparation of 4-(4-(1,1-Difluoroethyl)phenyl)-6-nitrobenzo[d]thiazole A mixture of 4-bromo-6-nitrobenzo[d]thiazole (5.0 g, 19.3 mmol), 2-(4-(1,1- difluoroethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (6.21 g, 23.16 mmol), Pd(dppf)Cl2 (1.41 g, 1.93 mmol), K2CO3 (8.0 g, 57.9 mmol) in 1,4-dioxane (50 mL) and water (5 mL) was stirred at 100°C for 2 hours under a N2atmosphere. The reaction mixture was concentrated under vacuum. The residue was purified by flash chromatography on silica gel (0 - 25% ethyl acetate in petroleum ether) to afford the title compound (5.5 g, 89%) as a yellow solid.
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Chemical Structure| 214360-65-3

[ 214360-65-3 ]

4,4,5,5-Tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

Similarity: 0.88

Chemical Structure| 1256358-84-5

[ 1256358-84-5 ]

4,4,5,5-Tetramethyl-2-(3-methyl-5-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

Similarity: 0.86

Chemical Structure| 1234319-14-2

[ 1234319-14-2 ]

2-(4-(Difluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.90

Chemical Structure| 214360-65-3

[ 214360-65-3 ]

4,4,5,5-Tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

Similarity: 0.88

Aryls

Chemical Structure| 1234319-14-2

[ 1234319-14-2 ]

2-(4-(Difluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.90

Chemical Structure| 214360-65-3

[ 214360-65-3 ]

4,4,5,5-Tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

Similarity: 0.88

Chemical Structure| 1234319-14-2

[ 1234319-14-2 ]

2-(4-(Difluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.90

Chemical Structure| 214360-65-3

[ 214360-65-3 ]

4,4,5,5-Tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

Similarity: 0.88

Chemical Structure| 1256358-84-5

[ 1256358-84-5 ]

4,4,5,5-Tetramethyl-2-(3-methyl-5-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

Similarity: 0.86

Esters

Chemical Structure| 1234319-14-2

[ 1234319-14-2 ]

2-(4-(Difluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.90

Chemical Structure| 627525-89-7

[ 627525-89-7 ]

2-(3-(Difluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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Chemical Structure| N/A

[ N/A ]

2-(6-(Difluoromethyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.88

Chemical Structure| 1234319-14-2

[ 1234319-14-2 ]

2-(4-(Difluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.90

Chemical Structure| 627525-89-7

[ 627525-89-7 ]

2-(3-(Difluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.89