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[ CAS No. 916587-44-5 ]

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Chemical Structure| 916587-44-5
Chemical Structure| 916587-44-5
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CAS No. :916587-44-5 MDL No. :MFCD03490498
Formula : C18H28BNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :333.23 g/mol Pubchem ID :-
Synonyms :

Safety of [ 916587-44-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P272-P273-P280-P302+P352-P333+P313-P363-P501 UN#:
Hazard Statements:H317-H413 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 916587-44-5 ]

  • Downstream synthetic route of [ 916587-44-5 ]

[ 916587-44-5 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 916587-44-5 ]
  • [ 1014613-05-8 ]
  • [ 1014613-23-0 ]
YieldReaction ConditionsOperation in experiment
97% With sodium carbonate In 1,4-dioxane; water at 150℃; for 0.5h; Microwave irradiation; 4-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-6]pyridine (0.100g, 0.284mmol) 1,1- dimethylethyl methyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (0.144g, 0.427mmol), bis(diphenylphosphino)ferrocene palladium (II) chloride (0.023g, 0.0284mmol) and sodium carbonate (0.09Og, 0.852mmol) in dioxan (3.5ml) and water (0.7ml) were heated in the Biotage Initiator mw at 150°C for 30 min. The reaction mixture was partitioned between DCM (10ml) and saturated citric acid : water (1:2, 15ml). The aqueous phase was extracted with DCM (10ml). The combined organic extracts were concentrated and the dark residue purified by FlashMaster on silica using EtOAc - cyclohexane (0-100%). The desired fractions were combined and concentrated in vacuo to give the title compound as a white solid (0.132g, 97%). MH+478, rt= 1.41 min
  • 2
  • [ 73183-34-3 ]
  • [ 306768-12-7 ]
  • [ 916587-44-5 ]
YieldReaction ConditionsOperation in experiment
63% With potassium acetate In dimethyl sulfoxide at 80℃; for 3.5h;
63% With CH3COOK; PdCl2(Fe(C5H4P(C6H5)2)2)*CH2Cl2 In dimethyl sulfoxide (N2); addn. of soln. of carbamic acid deriv. in DMSO to mixture of boroncompd., palladium compd. and potassium acetate, stirring at 80°C for 3.5 h; cooling to room temp., addn. of ethyl acetate, washing with water, drying with MgSO4, concn., chromy. (silica gel, hexanes/ethyl acetate (8:1)),NMR;
  • 3
  • [ 916587-44-5 ]
  • [ 926622-39-1 ]
  • 3-{3-[4'-(tert-butoxycarbonylmethylamino)biphenyl-3-ylsulfanyl]benzyl}-3H-imidazole-4-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With potassium carbonate In 1,2-dimethoxyethane at 80℃; for 24h;
  • 4
  • [ 916587-44-5 ]
  • 3-{3-[4'-(tert-butoxycarbonylmethylamino)biphenyl-3-ylsulfanyl]benzyl}-3H-imidazole-4-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 63 percent / K2CO3 / PdCl2(dppf)*CH2Cl2 / 1,2-dimethoxy-ethane / 24 h / 80 °C 2: 93 percent / NaOH / methanol; H2O / 24 h / 20 °C
  • 5
  • [ 916587-44-5 ]
  • 3-[3-(4'-methylaminobiphenyl-3-ylsulfanyl)benzyl]-3H-imidazole-4-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 63 percent / K2CO3 / PdCl2(dppf)*CH2Cl2 / 1,2-dimethoxy-ethane / 24 h / 80 °C 2: 99 percent / CF3COOH / CH2Cl2 / 2 h / 20 °C
  • 6
  • [ 916587-44-5 ]
  • C29H28ClN3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 63 percent / K2CO3 / PdCl2(dppf)*CH2Cl2 / 1,2-dimethoxy-ethane / 24 h / 80 °C 2: 93 percent / NaOH / methanol; H2O / 24 h / 20 °C 3: DMF / CH2Cl2; toluene / 1 h / 0 °C
  • 7
  • [ 916587-44-5 ]
  • 3-(3-{4'-[(3-{3-[4'-(tert-butoxycarbonylmethylamino)biphenyl-3-ylsulfanyl]benzyl}-3H-imidazole-4-carbonyl)methylamino]biphenyl-3-ylsulfanyl}benzyl)-3H-imidazole-4-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 63 percent / K2CO3 / PdCl2(dppf)*CH2Cl2 / 1,2-dimethoxy-ethane / 24 h / 80 °C 2: 93 percent / NaOH / methanol; H2O / 24 h / 20 °C 3: DMF / CH2Cl2; toluene / 1 h / 0 °C 4: 0.94 g / pyridine; CH2Cl2 / 20 °C
Multi-step reaction with 3 steps 1: 63 percent / K2CO3 / PdCl2(dppf)*CH2Cl2 / 1,2-dimethoxy-ethane / 24 h / 80 °C 2: 99 percent / CF3COOH / CH2Cl2 / 2 h / 20 °C 3: 0.94 g / pyridine; CH2Cl2 / 20 °C
  • 8
  • [ 24424-99-5 ]
  • [ 916587-44-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 83 percent / Et3N; DMAP / CH2Cl2 / Heating 2: 63 percent / KOAc / PdCl2(dppf)*CH2Cl2 / dimethylsulfoxide / 3.5 h / 80 °C
Multi-step reaction with 3 steps 1.1: <i>tert</i>-butyl alcohol / 24 h / 40 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 2.2: 12 h / 0 - 20 °C / Inert atmosphere 3.1: tricyclohexylphosphine; [Rh(OH)(cod)]2 / hexane / 1 h / 80 °C / Glovebox; Inert atmosphere 3.2: 12 h / 80 °C / Glovebox; Inert atmosphere
  • 9
  • [ 60577-34-6 ]
  • [ 916587-44-5 ]
  • 10
  • [ 916587-44-5 ]
  • [ 894772-82-8 ]
  • tert-butyl N-methyl-N-[4-(4,4-dioxo-4-thia-2,5,9-triaza-1(2,4)-pyrimidina-3(1,3)-benzenacyclononaphan-15-yl)phenyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 2h; 1 (Typical Scale: 0.25 mmol) A solution of the respective macrocyclic halide in DMF (8 mL per mmol halide) was treated with the respective organoboron compound (1.25 eq.), K2CO3 (2.5 eq., either as a solid or as 2 M aqueous solution), and POPd (2.5-5 mol-%) at room temperature. The stirred resulting mixture was placed into an oil bath preheated to 100° C. The reaction progress was monitored by TLC, and in case of incomplete turnover of the macrocyclic halide after 2 h additional portions of POPd and the organoboron compound were added followed by additional stirring at 100° C. After cooling to room temperature, water was added and the resulting suspension was stirred for 30 min. The crude product was isolated by vacuum filtration, dried in vacuo, and purified by column chromatography, followed optionally by trituration with methanol and/or preparative HPLC (e.g. YMC Pro C18RS 5μ, 150×20 mm, 0.2% NH3 in water/acetonitrile) to yield the analylically pure products. Alternatively, after full conversion the reaction mixture was diluted with ethyl acetate, quenched with water. Layers were separated, the organic layer was extracted with ethyl acetate twice and the combined organic layers dried and concentrated in vacuo followed by the above mentioned further purification steps.; Intermediate 10 was prepared according to GP 1 from 15-iodo-4-thia-2,5,9-triaza-1(2,4)-pyrimidina-3(1,3)-benzenacyclononaphan-4,4-dioxide and tert-butyl N-methyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate. 1H-NMR (DMSO, 400 MHz): 9.58 (s, 1H); 9.42 (s, 1H); 7.77 (s, 1H); 7.73 (t br, 1H); 7.31-7.38 (m, 5H); 7.26 (t br, 2H); 6.95 (t br, 1H); 3.32-3.44 (m, 2H); 3.20-3.28 (m, 2H); 3.18 (s, 3H); 1.74-1.87 (m, 2H); 1.38 (s, 9H). MS (ESI): [M+H]+=511.
  • 11
  • [ 916587-44-5 ]
  • [ 10397-13-4 ]
  • [ 1155306-49-2 ]
YieldReaction ConditionsOperation in experiment
Example 13 N-[4-(2>-Amino-2-morpholin-4-vH4,5'lbipyrimidinvI-6-yl)- phenyll-N-methyl-methanesulfonamide (56) Standard Suzuki reaction betwen Intermediate Al and t-butyl-N-methyl-N-[4-(tetramethyldioxaboronyl)phenyl]carbamate yielded [4-(6-chloro-2-morpholm-4-yl- pyrimidin-4-yl)-phenyl]-methyl-carbamic acid tert-butyl ester. Cleavage of the BOC grup using HCl in ether yielded [4-(6-chloro-2-morpholin-4-yl-pyrimidin-4-yl)-phenyl]- methyl-amine.Reaction of [4-(6-chloro-2-morpholin-4-yl-pyrimidin-4-yl)-phenyl]-methyl- amine with methane sulphonyl chloride in dichloromethane using triethylamine as base yielded N-[4-(6-chloro-2-mophiholin-4-yl-pyrimidin-4-yl)-phenyl]-N-methyl- methanesulfonamide. <n="96"/>Reaction of N-[4-(6-chloro-2-mthetaphiholin-4-yl-pyrimidin-4-yl)-phenyl]-N- methyl-methanesulfonamide with 2-aminopyrimidine-5-boronic acid, pinacol ester using standard Suzuki conditions yielded the desired title compound. NMR (CDCB): 2.90 (3H, s), 3.41 (3H, s), 3.84-3.87 (4H, m), 3.99-4.02 (4H, m), 5.29 (2H, br), 7.26 (IH, s), 7.53 (2H, d), 8.12 (2H, d), 9.30 (2H, s) MS (ESI+): MH+ 442.13 (10%), (MH+AcN) 483.2 (100%)
  • 13
  • [ 916587-44-5 ]
  • [ 5332-24-1 ]
  • [ 1246093-99-1 ]
YieldReaction ConditionsOperation in experiment
Preparation of N-Methyl-4-(quinolin-3-yl)aniline (T477) 3-Bromoquinoline (42 mg, 0.2 mmol) and tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (66 mg, 0.2 mmol) were reacted using General Procedure (A) to afford tert-butyl methyl(4-(quinolin-3-yl)phenyl)carbamate a clear wax (44 mg, 66%). 1H NMR (400 MHz, CDCl3): δ 9.18 (d, J=2.4 Hz, 1H), 8.31 (d, J=2.0 Hz, 1H), 8.15 (m, 1H), 7.89 (m, 1H), 7.73 (m, 1H), 7.68 (m, 2H), 7.59 (m, 1H), 7.42 (m, 2H), 3.3 (s, 3H), 1.50 (s, 9H); MS (ESI): 335 (M+H+).
  • 14
  • [ 916587-44-5 ]
  • [ 19493-45-9 ]
  • [ 1246094-00-7 ]
YieldReaction ConditionsOperation in experiment
18% Preparation of 3-Chloroisoquinoline (33 mg, 0.2 mmol) and tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (66 mg, 0.2 mmol) were reacted using general procedure A to afford tert-butyl (4-(isoquinolin-3-yl)phenyl)(methyl)carbamate as a clear oil (12 mg, 18%). 1H NMR (400 MHz, CDCl3): delta 9.33 (s, 1H), 8.09 (m, 2H), 8.05 (s, 1H), 7.99 (m, 1H), 7.87 (m, 1H), 7.69 (m, 1H), 7.58 (m, 1H), 7.38 (m, 2H), 3.32 (s, 3H), 1.48 (s, 9H); MS (ESI): 335 (M+H+).
  • 15
  • [ 916587-44-5 ]
  • [ 20146-63-8 ]
  • [ 1246093-98-0 ]
YieldReaction ConditionsOperation in experiment
68% tert-Butyl methyl(4-(4-nitroquinolin-2-yl)phenyl)carbamate 2-Bromo-4-nitroquinoline (50 mg, 0.2 mmol) and tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (66 mg, 0.2 mmol) were reacted using General Procedure (A) to afford tert-butyl methyl(4-(4-nitroquinolin-2-yl)phenyl)carbamate as a yellow oil (52 mg, 68%). 1H NMR (400 MHz, CDCl3): δ 8.43-8.40 (m, 2H), 8.28 (m, 1H), 8.19 (m, 2H), 7.87 (m, 1H), 7.73 (m, 1H), 7.46 (m, 2H), 3.35 (s, 3H), 1.59 (s, 3H), 1.50 (s, 9H); MS (ESI): 380 (M+H+).
68% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 100℃; for 0.5h; Microwave irradiation; tert-Butyl methyl(4-(4-nitroquinolin-2-yl)phenyl)carbamate General procedure: A mixture of aryl/heterocyclic halide (1.0 equiv.), boronic acid or boronate ester (1.1-1.5 equiv.), K2CO3 (3.0 equiv.) and Pd[PPh3]4 (0.01 -0.05 equiv) in DMF (30 mL) was irradiated in a Biotage Emrys Initiator microwave reactor (250 W) at 100 °C for 30 min. After cooling to room temperature, the solvent was removed in vacuo. The residue was purified on flash column chromatography over silica gel using EtOAc:Hexanes or EtOAc:DCM or MeOH:DCM as the eluent to afford the desired biaryl products. 2-Bromo-4-nitroquinoline (50 mg, 0.2 mmol) and tert-butyl methyl(4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)carbamate (66 mg, 0.2 mmol) were reacted using General Procedure (A) to afford tert-butyl methyl(4-(4-nitroquinolin-2-yl)phenyl)carbamate as a yellow oil (52 mg, 68%).
  • 16
  • [ 916587-44-5 ]
  • [ 1235382-38-3 ]
  • [ 1248555-83-0 ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere; 8a (8a) 2-(Trimethylsilyl)ethyl 4-{4-[(tert-butoxycarbonyl) (methyl)amino]phenyl}isoquinoline-6-carboxylate Into N,N-dimethylformamide (30 mL), 2-(trimethylsilyl)ethyl 4-[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylate (1.50 g, 3.56 mmol), potassium carbonate (2.46 g, 17.8 mmol), tert-butyl methyl--[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (1.78 g, 5.34 mmol), and a [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium-dichloromethane complex (291 mg, 0.356 mmol) were dissolved, followed by stirring at 90°C for one hour under a nitrogen atmosphere. After cooling, the resulting reaction liquid was concentrated under reduced pressure and a solid was filtered off, followed by washing with dichloromethane. The resulting organic layer was concentrated under reduced pressure again. The residue thus obtained was purified by basic silica gel column chromatography (hexane : ethyl acetate, 100 : 0 - 80 : 20, V/V) and by neutral silica gel column chromatography (hexane : ethyl acetate, 100 : 0 - 50 : 50, V/V) to give the desired title compound (1.28 g, yield 75%). 1H-NMR (CDCl3) δ: 0.04 (9H, s), 1.09-1.13 (2H, m), 1.50 (9H, s), 3.35 (3H, s), 4.41-4.46 (2H, m), 7.42 (2H, d, J = 8.6 Hz), 7.47 (2H, d, J = 8.6 Hz), 8.08 (1H, d, J = 8.5 Hz), 8.20 (1H, d, J = 8.5 Hz), 8.54 (1H, s), 8.66 (1H, s), 9.29 (1H, s).
  • 17
  • [ 916587-44-5 ]
  • [ 1248553-88-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 1 h / 90 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / Inert atmosphere 2.2: 4 h / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C 3.2: 0 °C 4.1: acetic acid / 4 h / 0 - 20 °C / Inert atmosphere
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