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[ CAS No. 1024017-53-5 ]

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Chemical Structure| 1024017-53-5
Chemical Structure| 1024017-53-5
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Product Details of [ 1024017-53-5 ]

CAS No. :1024017-53-5 MDL No. :MFCD03701685
Formula : C11H17BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :208.06 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1024017-53-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1024017-53-5 ]

  • Downstream synthetic route of [ 1024017-53-5 ]

[ 1024017-53-5 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 1024017-53-5 ]
  • [ 1082066-21-4 ]
  • [ 1082063-49-7 ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: (4-(tert-butoxymethyl)phenyl)boronic acid; 3'-chloro-4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl With potassium carbonate In ISOPROPYLAMIDE; water at 110℃; for 18.5h; Stage #2: With hydrogenchloride In water; acetonitrile 39m Example 39m: 3 '-(4-tert-Butoxymethyl-phenyl)-4-( 1,5 -dimethyl- lH-pyrazol-4- ylmethyl)-3,4,5,6-tetrahydro-2H-[l,2']bipyrazinyl hydrochloride --184-Dissolve 3'-chloro-4-(l,5-dimethyl-lH-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro- 2H-[l,2']bipyrazinyl (307 mg, 1.0 mmol) in N,N-dimethylacetamide (5 mL). Add potassium carbonate (332 mg, 2.40 mmol) then 4-tert-butoxymethyl benzene boronic acid (250 mg, 1.20 mmol), tetrakis(triphenylphosphine)palladium(0) (0.012 g, 0.01 mmol), then water (1 mL) and degas with nitrogen for 30 min. Heat at 1100C for 18 hr. Cool to room temperature, add water (5 mL) and extract with DCM (3 x 5 mL). Pass the combined DCM extracts through an 1ST Phase Separator Frit. Concentrate the filtrate and purify (silica gel chromatography, eluting with 0: 100 to 10:90 methanol: DCM), to give the free base as an oil. Dissolve the oil in acetonitrile and convert to the hydrochloride salt by adding 2 M aq HCl solution. Add water and lyophilize, then purify by SCX-2 chromatography washing with methanol then eluting with 2 M ammonia in methanol and concentrate. Further purify by low pH reverse phase HPLC. Form the free base by passing through an SCX-2 ion exchange cartridge washing with methanol then eluting with 2 M ammonia in methanol and concentrate. Dissolve the solid in acetonitrile and convert to the hydrochloride salt by adding 2 M aq HCl solution. Add water and lyophilize to give the title compound as yellow solid (274 mg, 58%). MS (ES): m/z = 435 [M+H]+
  • 2
  • [ 1024017-53-5 ]
  • [ 1186482-08-5 ]
  • [ 1186483-29-3 ]
YieldReaction ConditionsOperation in experiment
22 5-[6-(4-tert-Butoxymethyl-phenyl)-pyridazin-3-ylmethyl]-2-(2,3-difluoro-phenyl)-5H-imidazo[4,5-d]pyridazine (Compound 214) Example 22 5-[6-(4-tert-Butoxymethyl-phenyl)-pyridazin-3-ylmethyl]-2-(2,3-difluoro-phenyl)-5H-imidazo[4,5-d]pyridazine (Compound 214) From 5-(6-chloro-pyridazin-3-ylmethyl)-2-(2,3-difluoro-phenyl)-5H-imidazo[4,5-d]pyridazine and 4-(t-butoxymethyl-)-phenylboronic acid following general procedure A. MS 487.2 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 10.14 (s, 1H), 9.42 (s, 1H), 8.25-8.28 (m, 1H), 8.06-8.18 (m, 3H), 7.92-9.78 (m, 1H), 7.45-7.55 (m, 3H), 7.33-7.37 (m, 1H), 6.24 (s, 2H), 4.47 (s, 2H), 1.24 (s, 9H).
  • 3
  • [ 1024017-53-5 ]
  • [ 290368-00-2 ]
  • [ 1204772-87-1 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;palladium diacetate; tricyclohexylphosphine tetrafluoroborate; In 1,4-dioxane; at 100℃; for 3h; Reference Example 11; t-butyl-3-{4-(hydroxymethyl)phenyl}-1H-indazole-1-carboxylateTo a solution of the compound of Reference Example 7 (41.7 mg) in 1,4-dioxane (500 muL, manufactured by Kanto Chemical Co., Inc.), potassium phosphate (49 mg, manufactured by Wako Pure Chemical Industries, Ltd.), tricyclohexylphosphine-tetrafluoroborate (16.9 mg, manufactured by Sigma-Aldrich Corp.), palladium acetate (5.2 mg, manufactured by Kanto Chemical Co., Inc.), and 4-t-butoxymethylphenylboronic acid (29.5 mg, manufactured by Frontier Scientific, Inc.) were added, and the mixture was heated for 3 hours at 100 C. The reaction solution was cooled to room temperature, and then water (20 mL) was added thereto. The mixture was extracted with ethyl acetate (3×20 mL), washed with brine (20 mL), and dried (MgSO4). The solvent was then evaporated, to give 34.5 mg of the title compound. LC-MS: HPLC retention time 2.34 minutes, m/z 325 (M+H), condition C-2.
  • 4
  • [ 1024017-53-5 ]
  • [ 1309781-60-9 ]
  • (+/-)-cis-1-(4-(tert-butoxymethyl)phenyl)-2-tosyl-3-vinylisoindoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium phosphate; C44H44Cl2O2P2Pd2; barium(II) oxide In toluene at 80℃; for 12h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;
  • 5
  • [ 1024017-53-5 ]
  • [ 1353384-15-2 ]
  • [ 1353384-27-6 ]
YieldReaction ConditionsOperation in experiment
55% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 70 - 80℃; Inert atmosphere;
  • 6
  • [ 1024017-53-5 ]
  • (S)-ethyl 2-(5-bromo-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate [ No CAS ]
  • (S)-ethyl 2-(tert-butoxy)-2-(5-(4-(tert-butoxymethyl)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
37.4% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 110℃; for 2h; 48 (S)-Ethyl 2-(tert-butoxy)-2-(5-(4-(tert-butoxymethyl)phenyl)-4-(4, 4-dimethylpiperidin-]-yl)-2, 6-dimethylpyridin-3-yl)acetate: A mixture of(S)-ethyl 2-(5-bromo-4-(4,4-dimethylpiperidin- 1 -yl)-2, 6-dimethylpyridin-3 -yl)-2-(tert-butoxy)acetate (0.0475 g, 0.104 mmol), (4-(tert-butoxymethyl)phenyl)boronic acid (0.033 g, 0.156 mmol) and 2M Na2CO3 (0.130 ml, 0.261 mmol) in DMF (2 mL) was degassed for 10 mm. Then, Pd(Ph3P)4 (0.0 12 g, 10.43 tmol) was added, degassed for 5 mm and placed in a preheated oil bath at 110 °C. After 2 h, cooled and purified by prep-HPLC to afford (S)-64-ethyl 2-(tert-butoxy)-2-(5 -(4-(tert-butoxymethyl)phenyl)-4-(4,4-dimethylpiperidin- 1 -yl)2,6-dimethylpyridin-3-yl)acetate (0.021 g, 0.039 mmol, 37.4 % yield) as white solid. ‘H NMR (500 MFIz, CDC13) ö 7.40-7.45 (m, 2H), 7.23 (dd, J1.6, 7.9 Hz, 1H), 7.11-7.15 (dd, J1.6, 7.9 Hz, 1H), 6.08 (s, 1H), 4.56 (s, 2H), 4.26 (qd, J=7.1, 10.7 Hz, 1H), 4.18(qd, J7.1, 10.7 Hz, 1H), 3.20 (d, J=12.0 Hz, 1H), 2.88 (t, J=12.0 Hz, 1H), 2.61 (s, 3H),2.26 (d, J=11.8 Hz, 1H), 2.19 (s, 3H), 2.00 (t, J=11.6 Hz, 1H), 1.55 (dt, J=4.0, 12.5 Hz,1H), 1.32-1.39 (m, 1H), 1.34 (s, 9H), 1.26 (t, J=7.1 Hz, 3H), 1.21 (s, 9H), 1.16-1.20 (m,1H), 1.05 (d, J=12.5 Hz, 1H), 0.89 (s, 3H), 0.62 (s, 3H). LCMS (M+H) = 539.5.
  • 7
  • [ 1024017-53-5 ]
  • (S)-ethyl 2-(5-bromo-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate [ No CAS ]
  • (S)-2-(tert-butoxy)-2-(5-(4-(tert-butoxymethyl)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 2 h / 110 °C 2: lithium hydroxide; water / ethanol / 3 h / Reflux
  • 8
  • [ 1024017-53-5 ]
  • 3-bromo-5-(methylsulfonyl)-4H-1,2,4-triazole [ No CAS ]
  • C14H19N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In water; N,N-dimethyl-formamide at 100℃;
  • 9
  • [ 1024017-53-5 ]
  • [ 91-56-5 ]
  • (E)-2-(1-(4-(tert-butoxymethyl)phenyl)-2-oxoindolin-3-ylidene)hydrazine-1-carboximidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper diacetate; triethylamine / dichloromethane / Molecular sieve 2: acetic acid / 20 °C
  • 10
  • [ 1024017-53-5 ]
  • [ 91-56-5 ]
  • C19H19NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper diacetate; triethylamine In dichloromethane Molecular sieve; General procedures for the synthesis of compound 5a - 5p: General procedure: To amixture of phenylboronic acid (0.30 mmol), isatin (0.33 mmol), copper(II) acetate (0.30 mmol) and triethylamine (125 μL) in dichloromethane(10 mL), dried molecular sieve (4) was added. The mixture was thenallowed to react with stirring for 60 h at room temperature. Excessiveisatin was removed by silica gel chromatography using a mobile phaseof ethyl acetate: petroleum ether = 1:4. Some vacuum dried product(0.15 mmol) was further reacted with aminoguanidine HCl salt(0.27 mmol) with acetic acid (20 mL) as the solvent. The reactionmixture was allowed to stir for 2 h at room temperature. The crudeproducts were precipitated by the addition of diethyl ether (200 mL)into the reaction mixture and were collected by filtration. The pureproduct was isolated as a yellowish solid after the purification with silica gel chromatography using a mobile phase of methanol: dichloromethane= 1: 4.
  • 11
  • [ 1024017-53-5 ]
  • C26H32IN5O4S [ No CAS ]
  • C37H47N5O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With dicyclohexyl({2’,6’-dimethoxy-[1,1‘-biphenyl]-2-yl})phosphane; palladium diacetate; Cs2CO3 In tetrahydrofuran at 120℃; for 1h; Microwave irradiation; Inert atmosphere; 3-(3-HO-Me-Ph)-Phs-Phe(3-CN)-Pip-4-Urea-tBu (S18) General procedure: The halide S9 (100 mg, 0.16 mmol, 1.0 eq.), 3-(hydroxymethyl)-phenylboronic acid (33 mg, 0.22 mmol, 1.4 eq.), Pd(OAc)2 (1.1 mg, 4.7 μmol, 3 mol%), and SPhos (3.9 mg, 9.4 μmol, 6 mol%) were dissolved in 1 mL THF and 0.31 mL 2 M aq. Cs2CO3 solution (2 mL/mmol halide) in a microwave vial. After passing Ar into the solution for 5 min, the vial was sealed and the mixture stirred in a microwave at 120 °C for 80 min. The reaction mixture was cooled to room temperature and diluted with EtOAc. The organic phase was submitted to a series of washing steps (2 x Aq.demin → 1 x brine), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Lastly, the obtained crude was purified via column chromatography (silica gel, EtOAc/MeOH 100:1) to obtain the pure product S18 as a colorless solid (56 mg, 91 μmol).
58% With dicyclohexyl({2’,6’-dimethoxy-[1,1‘-biphenyl]-2-yl})phosphane; palladium diacetate; Cs2CO3 In tetrahydrofuran at 120℃; for 1h; Microwave irradiation; Inert atmosphere; 3-(3-HO-Me-Ph)-Phs-Phe(3-CN)-Pip-4-Urea-tBu (S18) General procedure: The halide S9 (100 mg, 0.16 mmol, 1.0 eq.), 3-(hydroxymethyl)-phenylboronic acid (33 mg, 0.22 mmol, 1.4 eq.), Pd(OAc)2 (1.1 mg, 4.7 μmol, 3 mol%), and SPhos (3.9 mg, 9.4 μmol, 6 mol%) were dissolved in 1 mL THF and 0.31 mL 2 M aq. Cs2CO3 solution (2 mL/mmol halide) in a microwave vial. After passing Ar into the solution for 5 min, the vial was sealed and the mixture stirred in a microwave at 120 °C for 80 min. The reaction mixture was cooled to room temperature and diluted with EtOAc. The organic phase was submitted to a series of washing steps (2 x Aq.demin → 1 x brine), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Lastly, the obtained crude was purified via column chromatography (silica gel, EtOAc/MeOH 100:1) to obtain the pure product S18 as a colorless solid (56 mg, 91 μmol).
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