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[ CAS No. 199609-62-6 ] {[proInfo.proName]}

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Chemical Structure| 199609-62-6
Chemical Structure| 199609-62-6
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Product Details of [ 199609-62-6 ]

CAS No. :199609-62-6 MDL No. :MFCD06246052
Formula : C12H18BNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :YHAQUGOSDQZIMA-UHFFFAOYSA-N
M.W : 251.09 Pubchem ID :3684686
Synonyms :

Safety of [ 199609-62-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280 UN#:N/A
Hazard Statements:H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 199609-62-6 ]

* 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 [ 199609-62-6 ]

[ 199609-62-6 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 199609-45-5 ]
  • [ 199609-62-6 ]
  • [3-(4,5,6-Trimethoxy-7-oxo-cyclohepta-1,3,5-trienyl)-benzyl]-carbamic acid tert-butyl ester [ No CAS ]
  • 2
  • [ 52415-29-9 ]
  • [ 199609-62-6 ]
  • [3-(1H-Indol-6-yl)-benzyl]-carbamic acid tert-butyl ester [ No CAS ]
  • 3
  • [ 10075-50-0 ]
  • [ 199609-62-6 ]
  • [3-(1H-Indol-5-yl)-benzyl]-carbamic acid tert-butyl ester [ No CAS ]
  • 4
  • [ 199609-62-6 ]
  • [ 210889-34-2 ]
  • 3-{7-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-1H-indol-3-yl}-propionic acid ethyl ester [ No CAS ]
  • 5
  • [ 199609-62-6 ]
  • [ 210889-33-1 ]
  • 3-{6-[3-(tert-Butoxycarbonylamino-methyl)-phenyl]-1H-indol-3-yl}-propionic acid ethyl ester [ No CAS ]
  • 6
  • [ 909036-40-4 ]
  • [ 199609-62-6 ]
  • [ 909036-41-5 ]
  • 7
  • [ 1003933-74-1 ]
  • [ 199609-62-6 ]
  • [ 1003933-78-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; at 100℃; for 0.5h;microwave irradiation; EXAMPLE 227; 5-[3'-(aminomethyI)biphenyl-3-yl]-l,4-dihydroxy-l,8-naphthyridin-2-(l H)-one; Step 1 : ter/-butyl ({3'-[8-benzyloxy)-5-hydroxy-7-oxo-7,8-dihydro-l ,8-naphthyridin-4- yl]biphenyl-3-yl}methyl) carbamate; The Ethyl l-(benzyloxy)-5-( 3-bromophenyl)-4-hyroxy-2-oxo-l,2-dihydro-l,8- naphthyridine-3-carboxylate (Example 225, Step 4, 0.100 g3 0.202 mmol) was dissolved in DMF (5.0 mL) and H2O (1.0 mL). To this was added 3-(N-BOC-aminomethyl)phenylboronic acid (0.101 g, 0.404 mmol), potassium carbonate (0.084 g, 0.606 mmol), and the Pd dppf (DCM adduct) catalyst (0.008 g, 0.010 mmol) while N2 was bubbled through the solution. The reaction vessel was sealed and the reaction heated in a microwave at 1000C for 0.5 hour. The solution was cooled to room temperature, diluted with H2O ( 6 mL), and extracted into EtOAc (3x 10 mL). The organic layers were combined, dried, filtered, and concentrated. The residue was purified by SGC (0-50% EtOAc/hexane) to afford the title compound. ES MS: m/z = 622 (M +
  • 8
  • [ 1003933-82-1 ]
  • [ 199609-62-6 ]
  • [ 1003933-86-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; at 100℃; for 0.166667h;microwave irradiation; Step 2: tert-butyl [(3'-[l-(benzyloxy)-2-oxo-l,2-dihyrdo-l,8-naphmvridm-4- yl]methyl}biphenyl-3-yl)methyl]carbamate; The l-(benzyloxy)-4-(3-bromobenzyl)-l,8-naphthyridin-2(l H)-one (0.150 g, 0.356 mmol) was dissolved in DMF (5.0 mLs) and H2O (1.0 mL). To this was added 3-(N-BOC- aminomethyl)phenylboronic acid (0.179 g, 0.712 mmol), potassium carbonate (0.148 g, 1.068 mmol), and the Pd dppf (DCM adduct) catalyst (0.015 g, 0.018 mmol) while N2 was bubbled through the solution. The reaction vessel was sealed and the reaction heated in a microwave at 100 0C for 10 minutes. The solution was cooled to room temperature, diluted with aqueous HCl (IN, 6 mL), and extracted into EtOAc (10 mL). The organic layer was dried, filtered, and concentrated. ES MS: m/z - 548 (M + 1).
  • 9
  • [ 1003934-37-9 ]
  • [ 199609-62-6 ]
  • [ 1003934-41-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; N,N-dimethyl-formamide; at 100℃; for 0.5h;microwave irradiation; Step 2: ethyl 1 -(benzyloxy)-5-[(3'-[(tert-butoxycarbonyl)amino]methyl}biphenyl-3- yl)methyl]-4-hydroxy-2-oxo-l ,2-dihydro-l, S-naphthyridine-S-carboxylate.; Ethyl l-(benzyloxy)-5-(3-bromoben2yl)-4-hydroxy-2-oxo-l,2-dihydro-l,8- naphthyridine-3-carboxylate: from step 1 (0.200 g, 0.41 mmol) was dissolved in DMF (5.0 mL) and H2O (1.0 mL). To this was added 3-(N-BOC-aminomethyl)phenylboronic acid (0.101 g, 0.404 mmol), K2CO3 (0.084 g, 0.606 mmol), and the Pd dppf (DCM adduct) catalyst (0.008 g,0.010 mmol) while N2 was bubbled through the solution. The reaction vessel was sealed and the reaction heated in a microwave at 1000C for 0.5 hour. The solution was cooled to room temperature, diluted with H2O (6 mL), and extracted into EtOAc (3x 10 mL). The organic layers were combined, dried, filtered, and concentrated. The residue was purified by SGC (0-100% EtOAc/hexane) to afford the title compound (150 mgs). ES MS: m/z = 636.1 (M + 1).
  • 10
  • [3-(aminomethyl)phenyl]boronic acid [ No CAS ]
  • [ 199609-62-6 ]
YieldReaction ConditionsOperation in experiment
For compounds (2-6) the commercially available 4-aminomethylphenylboronic acid and 3-aminomethylphenylboronic acid were BOC protected under standard conditions (Wei et al., 2000) and the appropriate boronic acid was used at the Suzuki coupling stage in the synthesis of compounds (2-6). The BOC group was removed with 4 M HCl in dioxane at RT after hydrazone coupling;
  • 11
  • [ 905735-46-8 ]
  • [ 199609-62-6 ]
  • [ 905735-59-3 ]
YieldReaction ConditionsOperation in experiment
83% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In erthanol; water; toluene; at 95℃; for 0.5h; Example A9; 7-[3-(aminomethyl)phenyl]-1-methyl-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-4-amine trifluoroacetate salt; A9.1: 4-Chloro-7-[3-(t-butyloxycarbonylaminomethyl)phenyl]-1-methyl-1H-imidazo[4,5-d]thieno[3,2-b]pyridine; A mixture of A2.8 (620 mg; 2.05 mmol), 3-(N-Bocaminomethyl)phenylboronic acid, [purchased from Frontier Scientific] (652 mg; 2.60 mmol), tetrakis(triphenylphosphine)palladium(0) (60 mg; 0.048 mmol), 2M Na2CO3 (4 ml), ethanol (5 ml) and toluene (8 ml) was vigorously stirred at 95 C. for 0.5 hr. After cooling to rt, the reaction mixture was partitioned between ethyl acetate (100 ml) and water (25 ml). After drying (MgSO4), the organic layer was concentrated to afford a yellow oil, that was chromatographed on a 5×15 cm silica gel column using a stepwise gradient from 100% dichloromethane to 3% methanol in dichloromethane. The purest fractions were concentrated to afford 729 mg (83%) of A9.1 as a light yellow foam. 1H-NMR (CDCl3) δ: 7.97 (1H, s), 7.82 (1H, s), 7.63 (2H, m), 7.44 (2H, t, J=7.5 Hz), 7.33 (1H, d, J=7.5 Hz), 4.95 (1H, m), 4.40 (2H, d, J=5.5 Hz), 4.16 (3H, s), 1.48 (9H, s) HPLC (A): 99%, ret. time 1.86 min., LC/MS (M+H)+=429.12 (431.12).
  • 12
  • [ 887147-33-3 ]
  • [ 199609-62-6 ]
  • [[3-[8-methyl-5-(methylamino)-8H-imidazo[4,5-d]thiazolo[4,5-b]pyridin-2-yl]phenyl]methyl]carbamic acid 1,1-dimethylethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; ethanol; water; at 100℃; for 0.833333h; Example A44; rr3-r8-methyl-5-(methylamino')-8H-imidazor4.5-dlthiazolo[4,5-b]pyridin-2- yllphenyllmethyll carbamic acid 1,1 -dimethyl ethyl ester; A44A3.3 (25 mg, 0.084 mmol), 3-(t-butyloxycarbonylaminomethyl)phenylboronic acid (21 mg, 0.085 mmol) and tetrakis(triphenylphosphine)palladium (0) (9.7mg, 0.008 mmol) was added to a mixture of 2M aqueous sodium carbonate (0.18 mL) dioxane83 EPO <DP n="85"/>(0.40 mL) and ethanol (0.40 mL). The reaction mixture was heated under argon for 50 minutes at 100 0C. The reaction mixture allowed to cool to room temperature and the solvents were removed under reduced pressure. Water (6 mL) was added and placed in an ice bath. The precipitate was collected by filtration, washed with additional water and dried under vacuum. The solid was rinsed with hexane to yield 38.8 mg of a tan solid. The crude product was purified by flash silica gel column chromatography (98:2 ethyl acetate/methanol -^ 50:48:1:1 THF/ethyl acetate/methanol/ammonium hydroxide -> 50:45:3:2 THF/ethyl acetate/methanol/ammonium hydroxide. Fractions for which the desired mass were obtained were combined and the solvent removed under reduced pressure. The solid was suspended in hexane, filtered and rinsed with additional hexane. The solid was then triturated with a mixture of 90:10 ether/ethyl acetate to yield 10.4 mg of the desired product as a pale yellow solid. M+H+ = 425.24. 1H NMR 400 MHz ^6DMSO 5 8.24 s, IH, 8.06-7.90 m, 2H, 7.60-7.48, m, 2H, 7.40 br s, 1 H, 7.10 br s, IH, 4.24 br s, 2H, 4.06, s, 3H, 3.06, br s, 3H, 1.48 s, 9H.
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Technical Information

? Acyl Group Substitution ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Ester Cleavage ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Mannich Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Nomenclature of Ethers ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Preparation of Ethers ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Ethers ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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; ;