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[ CAS No. 909187-39-9 ]

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Chemical Structure| 909187-39-9
Chemical Structure| 909187-39-9
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Product Details of [ 909187-39-9 ]

CAS No. :909187-39-9 MDL No. :MFCD06801731
Formula : C8H11BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :165.98 g/mol Pubchem ID :-
Synonyms :

Safety of [ 909187-39-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 909187-39-9 ]

  • Downstream synthetic route of [ 909187-39-9 ]

[ 909187-39-9 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 142010-72-8 ]
  • [ 909187-39-9 ]
  • 2,2'-Bis-methoxymethoxy-3-(2-methoxy-3-methyl-phenyl)-[1,1']binaphthalenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
With barium dihydroxide; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 80℃; for 12h;
  • 2
  • [ 909187-39-9 ]
  • [ 175476-73-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Ba(OH)2*8H2O, Pd(PPh3)4 / 1,2-dimethoxy-ethane; H2O / 12 h / 80 °C 2: 4M aq. HCl / tetrahydrofuran / 5 h / Heating 3: BBr3 / CH2Cl2 / 1 h / 0 °C
  • 3
  • [ 909187-39-9 ]
  • 3-(2-Methoxy-3-methyl-phenyl)-[1,1']binaphthalenyl-2,2'-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Ba(OH)2*8H2O, Pd(PPh3)4 / 1,2-dimethoxy-ethane; H2O / 12 h / 80 °C 2: 4M aq. HCl / tetrahydrofuran / 5 h / Heating
  • 4
  • [ 52200-69-8 ]
  • [ 909187-39-9 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane at -70 - -20℃; for 0.5h; 89 To a solution of 2-bromo-6-methylphenol (0.520 g, 2.78 mmol) in 15 ML of acetone was added iodomethane (0.338 mL, 5.42 mmol) and potassium carbonate (0.768 g, 5.56 mmol). The reaction was heated to reflux and stirred overnight. Ammonium chloride (sat.) was added and the mixture was extracted with diethyl ether. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to afford 456 mg of 1-bromo-2-methoxy-3-methylbenzene as a clear oil. To a solution of 1-bromo-2-methoxy-3-methylbenzene (0.123 g, 0.61 mmol) in 3 mL of THF at -70° C. was added n-butyllithium (1.6 M in hexanes, 0.46 mL, 0.73 mmol) dropwise. The reaction stirred at -70° C. for 30 minutes and was then allowed to warm up to -20° C. Ammonium chloride (sat.) was added and the mixture was extracted with ethyl acetate, dried over sodium sulfate and filter to give 96 mg crude material. The crude material was purified by column chromatography (3/1 hexanes/ethyl acetate) to afford 40 mg of 2-methoxy-3-methylphenylboronic acid as a white solid. MS(ES+): 167.0 (M+H).
  • 5
  • 4-bromo-2-nitro-1-pentyl-1H-imidazole [ No CAS ]
  • [ 909187-39-9 ]
  • 4-(2-methoxy-3-methylphenyl)-2-nitro-1-pentyl-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane at 85℃; for 8h; Inert atmosphere;
  • 6
  • tert-butyl 3-(7-chloro-8-fluoro-2-((tetrahydro-1H-pyrrolizin-7a(5H)-yl)methoxy)pyrido[4,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]
  • [ 909187-39-9 ]
  • tert-butyl 3-(8-fluoro-2-((hexahydro-1H-pyrrolizin-7a-yl)methoxy)-7-(2-methoxy-3-methylphenyl)pyrido[4,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With potassium phosphate; [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate In tetrahydrofuran at 60℃; for 2h; Inert atmosphere; 313.A Step A. (1 R.5 SVtert-butvl 3 -(8 -fluoro-2-(Yhexahydro- lH-pyrrolizin-7 a- vOmethoxv)-7-(2-methoxv-3-methvlphenvOpvrido[4.3-d1pvrimidin-4-vO-3.8- diazabicvclor3.2.11octane-8-carboxvlate. A mixture of (lR,5S)-tert-butyl 3 -(7-chl oro- 8 -fluoro-2- ((hexahydro-lH-pyrrolizin-7a-yl)methoxy)pyrido[4,3-d]pyrimidin-4-yl)-3,8- diazabicyclo[3.2.1 ]octane-8-carboxylate (150 mg, 281 pmol, 1.00 eq), (2-methoxy-3-methyl- phenyl) boronic acid (142 mg, 855 pmol, 3.04 eq), [2-(2- aminophenyl)phenyl]palladium(l+);bis(l-adamantyl)-butyl-phosphane;methanesulfonate (41.0 mg, 56.3 pmol, 0.20 eq), and K3PO4 (1.50 M, 500 pL, 2.67 eq) in THF (2.0 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 60 °C for 2 hours under N2 atmosphere. After completion, the reaction mixture was diluted with H2O (5.0 mL) and extracted with ethyl acetate (3 c 10 mL). The combined organic layers were washed with saturated brine (30 mL), dried over Na2SOr, filtered and concentrated under reduced pressure to give a residue. The residue was purified by reversed phase flash chromatography [C18, 0.1% FA in water, 0-50% MeCN] affording the title compound (120 mg, 69% yield). White solid; NMR (400 MHz, CDCb-d) d = 9.02 (s, 1H), 7.32-7.27 (m, 2H), 7.16-7.11 (m, 1H), 4.56 (br d, J = 12.4 Hz, 2H), 4.39-4.36 (m, 2H), 4.19 (s, 2H), 3.77-3.58 (m, 2H), 3.55 (s, 3H), 3.15-3.07 (m, 2H), 2.68-2.60 (m, 2H), 2.38 (s, 3H), 2.13-2.04 (m, 2H), 1.99-1.93 (m, 2H), 1.90-1.83 (m, 4H), 1.81-1.73 (m, 2H), 1.71-1.62 (m, 2H), 1.53 (s, 9H); LCMS [ESI, M+l]: 619.3.
  • 7
  • [ 5419-55-6 ]
  • [ 578-58-5 ]
  • [ 909187-39-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-methylmethoxybenzene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane; cyclohexane at 5 - 20℃; for 7h; Large scale; Stage #2: Triisopropyl borate In hexane; tert-butyl methyl ether; cyclohexane at -70 - -20℃; Large scale; 1.1 Step 1 and 2 - Borylation of 2-Methylanisole [00176] The scale up was started using 40 kg (324 mol, 1 eq) 2-methylanisole (1), 50 kg TMEDA (1.3 eq) and 60 kg cyclohexane. n-Butyllithium solution (23% in hexanes, 115 kg, 1.3 eq) was added at 5-10 °C and after complete addition the line was rinsed with 30 kg cyclohexane. After 1 h at max. 10 °C, in process control (IPC) by HPLC with UV/Vis detection showed 20%area unreacted 2-methylanisole (peak at 10 min). The mixture was stirred at 5-20 °C for approx. 6 h total. At this point, IPC showed 10% area residual 2-methylanisole. (0260) [00177] The batch was cooled to -75 °C and MTBE (230 kg) was added during the cooling period at (0261) [00178] At this temperature the mixture was transferred to the quench reactor containing 15% aqueous HC1 (315 kg). IPCs showed residual 2-methylanisole at 6%area level. (0262) [00179] Subsequently, phases were separated, the organic layer was combined with water (240 kg) and 33% NaOH (53 kg) and layers were separated again. IPC showed no significant product content in the organic layer. (0263) [00180] The aqueous product solution was acidified and stirred for 2 h at (0264) [00181] The product (2, 48.5 kg; LOD: 21%) was additionally slurried with water (280 kg), filtered and the cake was washed with water (50 kg). The damp product resulting from this wash showed the expected purity (99.9%area). (0265) [00182] 42 kg of damp intermediate 2 was obtained. A sample (27 g) was dried in the lab overnight showing loss on drying (LOD) of -12%. The resulting dry product showed 103.6% potency by HPLC. Accordingly, yield for this step is calculated to be 38.3 kg (71%) 2-methoxy-3- methylphenylboronic acid.
  • 8
  • [ 909187-39-9 ]
  • [ 913836-10-9 ]
YieldReaction ConditionsOperation in experiment
With potassium permanganate; sodium hydroxide In lithium hydroxide monohydrate at 35℃; Large scale; 1.3 Step 3 - KMnC Oxidation [00183] Intermediate 2 (~38 kg dry product) was suspended in water (280 kg) and dissolved by addition of 33% NaOH solution (69 kg). Via solid lock, it was charged KMnO4 (100 kg total) starting with 5 kg portions. The exothermic effect observed after addition of a portion was in good agreement with the expected value of approx. 0.8-1 °C/kg. After addition of 30 kg, it was switched to 10 kg portions. A sample taken after 40 kg was showing the expected conversion level. Keeping the internal temperature at (0268) [00184] Damp intermediate 3 showing LOD of 19% was isolated (42.2 kg). This corresponded to 34.2 kg pure intermediate 3 (76%). Additionally, there was an amount of product sticking to the walls of the reactor (2-3 kg). The true yield of the reaction was therefore estimated to be at least 36 kg (80%). HPLC purity of the damp intermediate 3 by in-house analysis was 99.9% with 2-anisic acid and step 1 intermediate as the only impurities detected (each less than 0.1%).
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