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[ CAS No. 79326-88-8 ] {[proInfo.proName]}

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Product Details of [ 79326-88-8 ]

CAS No. :79326-88-8 MDL No. :MFCD09027273
Formula : C5H5BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :ZFUTWKQTEYLBKA-UHFFFAOYSA-N
M.W : 189.01 Pubchem ID :12742276
Synonyms :

Safety of [ 79326-88-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 79326-88-8 ]

* 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 [ 79326-88-8 ]

[ 79326-88-8 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 79326-88-8 ]
  • [ 1578484-83-9 ]
YieldReaction ConditionsOperation in experiment
94% With hydroxylamine hydrochloride; potassium carbonate In ethanol at 120℃; for 1h; Microwave irradiation; 155 Preparation 155: (£)-5-Bromo-1 -methyl-1 H-imidazole-2-carbaldehyde oxime Preparation 155: (£)-5-Bromo-1 -methyl-1 H-imidazole-2-carbaldehyde oxime A mixture of K2C03 (360 mg, 2.61 mmol), 5-bromo-1 -methyl-1 H-imidazole-2- carbaldehyde (98.5 mg, 0.521 mmol) and hydroxylamine hydrochloride (109 mg, 1 .563 mmol) in EtOH (4 mL) was stirred at ~ 20°C under microwave irradiation for 60 minutes. The resulting suspension was filtered, washing through with EtOAc and MeOH. The filtrate was concentrated in vacuo to afford the title compound as a white solid (100 mg, 94%). 1 H NMR (500 MHz, CDCI3): δ 8.17 (s, 1 H), 7.14 (s, 1 H), 3.86 (s, 3H).
  • 2
  • [ 79326-88-8 ]
  • [ 1099-45-2 ]
  • ethyl (E)-3-(5-bromo-1-methyl-1H-imidazol-2-yl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% In toluene for 16h; Inert atmosphere; Heating; Ethyl (E)-3-(5-bromo-1-methyl-1H-imidazol-2-yl)acrylate (164A) To a stirred solution of 5-bromo-l-methyl-1H-imidazole-2-carbaldehyde (2.5 g, 13.23 mmol) in toluene (50 mL) was added (carbethoxymethylene)triphenylphosphorane (6.91 g, 19.84 mmol) under nitrogen atmosphere. The resulting clear solution was heated to 110°C and stirred for 16h. After completion of the reaction, the reaction mixture was concentrated and the crude product was purified by combiflash chromatography (40 g Redisep Si02 column, eluting with 30% ethylacetate in n-hexanes) to afford the title compound 1 64A (2 g, 60%) as an off white solid. 1H NMR (400 MHz, DMSO-d6) ppm 7.56 (d, J=15.56 Hz, 1H), 7.23 (s, 1H), 6.60 (d, J=15.56 Hz, 1H), 4.21 (q,J=7.03 Hz, 2H), 3.72 (s, 3H), 1.27 (t,J=7.03 Hz, 3H).
  • 3
  • [ 79326-88-8 ]
  • ethyl 3-(5-bromo-1-methyl-1H-imidazol-2-yl)-3-(6-methoxypyridin-3-yl)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 16 h / Inert atmosphere; Heating 2: chloro(1,5-cyclooctadiene)rhodium(I) dimer; triethylamine / water; 1,4-dioxane / 16 h / Inert atmosphere; Heating
  • 4
  • [ 79326-88-8 ]
  • ethyl (E)-3-(5-(4-(1,8-naphthyridin-2-yl)but-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-3-(6-methoxy-pyridin-3-yl)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: toluene / 16 h / Inert atmosphere; Heating 2: chloro(1,5-cyclooctadiene)rhodium(I) dimer; triethylamine / water; 1,4-dioxane / 16 h / Inert atmosphere; Heating 3: triethylamine; tris-(o-tolyl)phosphine; palladium diacetate / acetonitrile / 16 h / 90 °C / Inert atmosphere
  • 5
  • [ 79326-88-8 ]
  • ethyl 3-(6-methoxypyridin-3-yl)-3-(1-methyl-5-(4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl)-1H-imidazol-2-yl)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: toluene / 16 h / Inert atmosphere; Heating 2: chloro(1,5-cyclooctadiene)rhodium(I) dimer; triethylamine / water; 1,4-dioxane / 16 h / Inert atmosphere; Heating 3: triethylamine; tris-(o-tolyl)phosphine; palladium diacetate / acetonitrile / 16 h / 90 °C / Inert atmosphere 4: platinum(IV) oxide; hydrogen / ethanol / 16 h / 20 °C
  • 6
  • [ 79326-88-8 ]
  • 4-chloro-2-(4-(1-methyl-2-(pyrrolidin-1-ylmethyl)-1H-imidazol-5-yl)phenoxy)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: dichloromethane / 0.42 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere 3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 80 °C
Multi-step reaction with 3 steps 1.1: dichloromethane / 0.25 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere 3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 80 °C
Multi-step reaction with 3 steps 1.1: dichloromethane / 0.42 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere 3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 80 °C
  • 7
  • [ 79326-88-8 ]
  • 4-(1-methyl-2-(pyrrolidin-1-ylmethyl)-1H-imidazol-5-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dichloromethane / 0.42 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: dichloromethane / 0.25 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: dichloromethane / 0.42 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere
  • 8
  • [ 79326-88-8 ]
  • 4-chloro-2-fluoro-6-(4-(1-methyl-2-(pyrrolidin-1-ylmethyl)-1H-imidazol-5-yl)phenoxy)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: dichloromethane / 0.42 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere 3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 23.5 h / 20 - 60 °C
  • 9
  • [ 79326-88-8 ]
  • methyl (S)-4-((R)-3-((S)-3-((4-chloro-2-(4-(1-methyl-2-(pyrrolidin-1-ylmethyl)-1H-imidazol-5-yl)phenoxy)benzyl)-L-alanyl)-2,2-dimethyloxazolidine-4-carboxamido)-3-(4-chlorobenzyl)piperidin-1-yl)-3-((R)-2,3-dihydro-1H-inden-1-yl)-4-oxobutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: dichloromethane / 0.42 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere 3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 80 °C 4.1: acetic acid / dichloromethane / 1 h / 20 °C 4.2: 16 h / 20 °C
  • 10
  • [ 123-75-1 ]
  • [ 79326-88-8 ]
  • 5-bromo-1-methyl-2-(pyrrolidin-1-ylmethyl)-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: pyrrolidine; 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde In dichloromethane at 20℃; for 0.416667h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1.75h; 7.7.1.1 Step 1.
5-Bromo-1-methyl-2-(pyrrolidin-1-ylmethyl)-1H-imidazole (E2-1) To a solution of 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (1.890 g, 10.0 mmol) in DCM (70 mL) was added pyrrolidine (1.643 mL, 20.0 mmol). After stirring for 25 min at rt NaBH(OAc)3 (8.48 g, 40.0 mmol) was added. The reaction mixture was stirred for 105 min at rt, and then concentrated to dryness in vacuo. The resulting residue was partitioned between EtOAc (250 mL) and 1 M aq. NaOH (50 mL). The organic phase was washed with 1 M NaOH (2*40 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated to dryness in vacuo to afford E2-1 (assumed to be 10.0 mmol) as a yellow solid. The crude product was used in the next step without purification. Analytical method 11; tR=0.66 min; [M+H]+=244.1.
Stage #1: pyrrolidine; 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde In dichloromethane at 20℃; for 0.25h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1.75h; 11.3.1 Step 1.5-Bromo-1-methyl-2-(pyrrolidin-1-ylmethyl)-1H-imidazole (F2-1) To a solution of 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (1.890 g, 10.0 mmol) in DCM (70 mL) was added pyrrolidine (1.643 mL, 20.0 mmol). After stirring for 25 min at rt NaBH(OAc)3(8.48 g, 40.0 mmol) was added. The resulting mixture was stirred for 105 min at rt, then concentrated to dryness in vacuo, and partitioned between EtOAc (250 mL) and 1 M aq. NaOH (50 mL). The organic layer was washed with 1 M NaOH (2 x 40 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated to dryness in vacuo to afford F2-1 (assumed to be 10.0 mmol) as a yellow solid. The crude product was used in the next step without purification. Analytical method 11; tR= 0.66 min; [M+H]+= 244.1.
Stage #1: pyrrolidine; 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde In dichloromethane at 20℃; for 0.416667h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1.75h; 1-3.1 Synthesis of 4-chloro-2-(4-( 1 -methyl-2-(pyrrolidin- 1 -ylmethyl)- 1 H-imidazol-5- yl)phenoxy)benzaldehyde (lnt-F2) Step 1. To a solution of 5-bromo-1 -methyl-1 H-imidazole-2-carbaldehyde (1.890 g, 10.0 mmol) in DCM (70 mL) was added pyrrolidine (1.643 mL, 20.0 mmol). After stirring for 25 min at rt NaBH(OAc)3(8.48 g, 40.0 mmol) was added. The resulting mixture was stirred for 105 min at rt, then concentrated to dryness in vacuo, and partitioned between EtOAc (250 mL) and 1 M aq. NaOH (50 mL). The organic layer was washed with 1 M NaOH (2 x 40 mL) and brine (20 mL), dried over Na2SO4filtered, and concentrated to dryness in vacuo to afford 5-bromo-1- methyl-2-(pyrrolidin-1 -ylmethyl)-1 H-imidazole (int-F2-1). The crude product was used in the next step without purification. Analytical method 11 ; tR= 0.66 min; [M+H]+= 244.1.
  • 11
  • [ 79326-88-8 ]
  • [ 71597-85-8 ]
  • 5-(4-hydroxyphenyl)-1-methyl-1H-imidazole-2-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 130℃; for 0.166667h; Inert atmosphere; Microwave irradiation; 11.2.1 Step 1.5-(4-Hydroxyphenyl)-1-methyl-1H-imidazole-2-carbaldehyde (F63-1) To a solution of 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (500 mg, 2.65 mmol), (4-hydroxyphenyl)boronic acid (547 mg, 3.97 mmol) and tetrakis(triphenylphosphine) palladium(0) (153 mg, 0.132 mmol) in DMF (7 mL) was added Na2CO3(1 M, 5.29 mL). The resulting mixture was purged with nitrogen gas before being irradiated in the microwave at 130 °C for 10 min. The reaction mixture was then poured into water and pH was adjusted to pH 6 with acetic acid. The reaction mixture was extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The resulting solid was triturated with a small amount of EtOAc to provide F63-1 as an orange solid (425 mg, 79%). Analytical method 5; tR= 0.47 min; [M+H]+= 203.1.
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 90℃; for 5h; Inert atmosphere; 7.7.2.1 Step 1.
5-(4-Hydroxyphenyl)-1-methyl-1H-imidazole-2-carbaldehyde (E3-1) A mixture of 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (1.890 g, 10 mmol), (4-hydroxyphenyl)boronic acid (2.76 g, 20.00 mmol) and Pd(PPh3)4(0.578 g, 0.500 mmol) in DMF (40 mL) and 1 M aq. Na2CO3 (30 mL, 30.0 mmol) was stirred for 5 h at 90° C. under an N2-atmosphere. The mixture was filtered through HyFlo and the filtrate was partitioned between EtOAc (100 mL) and H2O (50 mL). The aqueous phase was extracted with EtOAc (3*50 mL). The combined organic phases were washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated to dryness in vacuo to afford E3-1 (assumed to be 10 mmol) as an olive-colored solid.
  • 12
  • [ 79326-88-8 ]
  • C56H67Cl2N7O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: dichloromethane / 0.42 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere 3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 80 °C 4.1: acetic acid / dichloromethane / 1.5 h / 20 °C 4.2: 19.25 h / 20 °C 5.1: 1-hydroxy-7-aza-benzotriazole; HATU; 2,6-dimethylpyridine / dichloromethane / 25 h / 20 - 40 °C 5.2: 4 h / 40 °C
  • 13
  • [ 79326-88-8 ]
  • C56H65Cl2N7O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: dichloromethane / 0.42 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere 3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 80 °C 4.1: acetic acid / dichloromethane / 1 h / 20 °C 4.2: 16 h / 20 °C 5.1: water; sodium hydroxide / 1,4-dioxane / 5.5 h / 20 °C
  • 14
  • [ 79326-88-8 ]
  • C56H63Cl2N7O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: dichloromethane / 0.42 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere 3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 80 °C 4.1: acetic acid / dichloromethane / 1 h / 20 °C 4.2: 16 h / 20 °C 5.1: water; sodium hydroxide / 1,4-dioxane / 5.5 h / 20 °C 6.1: 1-hydroxy-7-aza-benzotriazole; HATU / dichloromethane / 0.08 h / 20 °C 6.2: 19.5 h / 40 °C
  • 15
  • [ 79326-88-8 ]
  • C53H60Cl2N8O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: dichloromethane / 0.42 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere 3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 80 °C 4.1: acetic acid / dichloromethane / 1 h / 20 °C 4.2: 2 h / 20 °C 5.1: water; sodium hydroxide / 1,4-dioxane / 0 - 20 °C 6.1: 1-hydroxy-7-aza-benzotriazole; HATU; 2,6-dimethylpyridine / dichloromethane / 19 h / Reflux
  • 16
  • [ 79326-88-8 ]
  • 4-chloro-2-(4-(1-methyl-2-(morpholinomethyl)-1H-imidazol-5-yl)phenoxy)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 5 h / 90 °C / Inert atmosphere 2.1: dichloromethane / 2.33 h / 20 °C 2.2: 2.5 h / 20 °C 3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 21 h / 80 °C
  • 17
  • [ 79326-88-8 ]
  • 4-(1-methyl-2-(morpholinomethyl)-1H-imidazol-5-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 5 h / 90 °C / Inert atmosphere 2.1: dichloromethane / 2.33 h / 20 °C 2.2: 2.5 h / 20 °C
  • 18
  • [ 79326-88-8 ]
  • (R)-N-((R)-1-(5-bromo-1-methyl-1H-imidazol-2-yl)ethyl)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(II) sulfate / dichloromethane / 20 °C 2: dichloromethane; diethyl ether / 1 h / -50 °C
  • 19
  • [ 79326-88-8 ]
  • (R)-1-(5-bromo-1-methyl-1H-imidazol-2-yl)ethanamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper(II) sulfate / dichloromethane / 20 °C 2: dichloromethane; diethyl ether / 1 h / -50 °C 3: hydrogenchloride / methanol; 1,4-dioxane / 1 h / 20 °C
  • 20
  • [ 79326-88-8 ]
  • 4-chloro-2-(4-(1-methyl-2-(pyrrolidin-1-ylmethyl)-1H-imidazol-5-yl)phenoxy)-6-(2,2,2-trifluoroethoxy)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: dichloromethane / 0.42 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere 3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 23.5 h / 20 - 60 °C 4.1: 43 h / 80 °C
  • 21
  • [ 79326-88-8 ]
  • 2-(4-(2-(azetidin-1-ylmethyl)-1-methyl-1H-imidazol-5-yl)phenoxy)-4-chlorobenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 5 h / 90 °C / Inert atmosphere 2.1: acetic acid / tetrahydrofuran / 1 h / 20 °C 2.2: 20 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.2: 2.5 h / 90 °C
  • 22
  • [ 79326-88-8 ]
  • 4-(2-(azetidin-1-ylmethyl)-1-methyl-1H-imidazol-5-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 5 h / 90 °C / Inert atmosphere 2.1: acetic acid / tetrahydrofuran / 1 h / 20 °C 2.2: 20 °C
  • 23
  • [ 79326-88-8 ]
  • 4-chloro-2-((5-(2-((dimethylamino)methyl)-1-methyl-1H-imidazol-5-yl)pyridin-2-yl)oxy)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol / 1 h / Cooling with ice 2.1: potassium carbonate; palladium diacetate; (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine / water; 1,4-dioxane / 16 h / 120 °C / Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / dichloromethane / 1 h / 20 °C 3.2: 20 °C
  • 24
  • [ 79326-88-8 ]
  • [ 861362-06-3 ]
YieldReaction ConditionsOperation in experiment
100% With methanol; sodium tetrahydroborate for 1h; Cooling with ice; 7.7.18 (5-Bromo-1-methyl-H-imidazol-2-yl)methanol E34-3 To a solution of 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (2 g, 10.58 mmol) in MeOH (30 mL) cooled in an ice bath, was added sodium borohydride (0.801 g, 21.16 mmol) in several portions. The resulting mixture was stirred in an ice bath for 60 min and then quenched with water and MeOH at 0° C. and concentrated in vacuo to dryness. The resulting residue was purified by flash chromatography (eluting with 0-40% DCM/MeOH) to afford E34-3 after concentrating the pure fractions under reduced pressure (2 g, quantitative yield).
  • 25
  • [ 79326-88-8 ]
  • 4-chloro-2-((5-(2-(hydroxymethyl)-1-methyl-1H-imidazol-5-yl)pyridin-2-yl)oxy)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol / 1 h / Cooling with ice 2: potassium carbonate; palladium diacetate; (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine / water; 1,4-dioxane / 16 h / 120 °C / Inert atmosphere
  • 26
  • [ 79326-88-8 ]
  • 4-(1-methyl-2-(((1-methylcyclopropyl)amino)methyl)-1H-imidazol-5-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 5 h / 90 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine / methanol / 2 h / 20 °C 2.2: 1 h / 0 °C / Cooling with ice
  • 27
  • [ 79326-88-8 ]
  • 4-(2-((ethyl(1-methylcyclopropyl)amino)methyl)-1-methyl-1H-imidazol-5-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 5 h / 90 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine / methanol / 2 h / 20 °C 2.2: 1 h / 0 °C / Cooling with ice 3.1: methanol / 1 h / 20 °C 3.2: 1 h / 20 °C
  • 28
  • [ 79326-88-8 ]
  • (3S,6S,9R,13S)-6-(tert-butoxymethyl)-1-(4-chloro-2-(4-(1-methyl-2-(pyrrolidin-1-ylmethyl)-1H-imidazol-5-yl)phenoxy)phenyl)-9-(4-chlorobenzyl)-13-((R)-2,3-dihydro-1H-inden-1-yl)-3,8,11-trimethyl-4,7,12-trioxo-2,5,8,11-tetraazapentadecan-15-oic acid trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: dichloromethane / 0.42 h / 20 °C 1.2: 1.75 h / 20 °C 2.1: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; 1,4-dioxane / 25 h / 100 °C / Inert atmosphere 3.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 18 h / 80 °C 4.1: acetic acid / dichloromethane / 1.5 h / 20 °C 4.2: 19.25 h / 20 °C
  • 29
  • [ 79326-88-8 ]
  • [ 196929-78-9 ]
  • (R,E)-N-((5-bromo-1-methyl-1H-imidazol-2-yl)methylene)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With copper(II) sulfate In dichloromethane at 20℃; 7.7.4.1 Step 1.
(R,E)-N-((5-Bromo-1-methyl-1H-imidazol-2-yl)methylene)-2-methylpropane-2-sulfinamide (E9-1) To 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (3 g, 15.87 mmol) in anhydrous DCM (40 mL) was added (R)-2-methylpropane-2-sulfinamide (2.116 g, 17.46 mmol) and anhydrous copper sulfate (5.07 g, 31.7 mmol). The resulting mixture was stirred at rt overnight, and then filtered through a pad of Celite, flushing with DCM. The filtrate was concentrated in vacuo and the crude product was purified by flash silica gel chromatography (eluting with 0→100% EtOAc in heptane) to afford E9-1 (4 g, 13.69 mmol, 86% yield) as a white solid. Analytical method 5; tR=0.83 min; [M+H]+=294.2.
86% With copper(II) sulfate In dichloromethane at 20℃; 11.13.1 Step 1. (R,E)-N-((5-Bromo-1-methyl-1H-imidazol-2-yl)methylene)-2-methylpropane-2- sulfinamide (F50-1) To 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (3 g, 15.87 mmol) in anhydrous DCM (40 mL) was added (R)-2-methylpropane-2-sulfinamide (2.116 g, 17.46 mmol) and copper sulfate anhydrous (5.07 g, 31.7 mmol). The resulting mixture was stirred at rt overnight and then filtered through a pad of celite, flushing with DCM. The filtrate was concentrated via rotary evaporation and purified by normal phase flash chromatography, using a silica gel column, eluting with 0-100% EtOAc in heptane to afford F50-1 (4 g, 13.69 mmol, 86% yield) as a white solid. Analytical method 5; tR= 0.83 min; [M+H]+= 294.2.
  • 30
  • [ 79326-88-8 ]
  • [ 124-40-3 ]
  • [(5-bromo-1-methyl-1H-imidazol-2-yl)methyl]dimethylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde; dimethyl amine In tetrahydrofuran; dichloromethane at 20℃; for 0.5h; Inert atmosphere; Molecular sieve; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran; dichloromethane at 0 - 20℃; for 16h; 11.1.1 Step 1. [(5-Bromo-1-methyl-1H-imidazol-2-yl)methyl]dimethylamine (F1-1) Into a 5-L 3-necked round-bottom flask, purged and maintained under aninert atmosphereof nitrogen, were placed 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (216 g, 1.14 mol, 1.00 equiv) and 4 Å molecular sieves in dichloromethane (3 L) and THF (1 L),followed by dimethylamine (862.5 mL, 1.50 equiv). The resulting mixture was stirred for 30 min at rt and NaBH(OAc)3(292.6 g, 1.38 mol, 1.20 equiv) was added batchwise at 0 ^C. The reaction mixture was stirred overnight at rt and then quenched with water (1 L). The organic phase was separated and washed with H2O (2 x 2 L). The aqueous phase was then extracted with DCM (2 x 1 L). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via silica gel column chromatography eluting with dichloromethane/ethyl acetate (2:1) to afford F1-1 (214.7 g, 86%) as a light yellow oil. Analytical method 5; tR= 0.60 min; [M+H]+= 220.1.
Stage #1: 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde; dimethyl amine In tetrahydrofuran; dichloromethane at 20℃; for 0.5h; Inert atmosphere; Molecular sieve; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran; dichloromethane at 0 - 20℃; Inert atmosphere; 1-3.1 Synthesis of 4-chloro-2-(4-(2-((dimethylamino)methyl)- 1 -methyl- 1 H-imidazol-5- yl)phenoxy)benzaldehyde (lnt-F1) Step 1 . Into a 5-L 3-necked round-bottom flask, purged and maintained under aninert atmosphereof nitrogen, were placed 5-bromo-1 -methyl-1 H-imidazole-2-carbaldehyde (216 g, 1 .14 mol, 1 .00 equiv) and 4 A molecular sieves in dichloromethane (3 L) and THF (1 L), followed by dimethylamine (862.5 mL, 1.50 equiv). The resulting mixture was stirred for 30 min at rt and NaBH(OAc)3(292.6 g, 1 .38 mol, 1.20 equiv) was added batchwise at 0 °C. The reaction mixture was stirred overnight at rt and then quenched with water (1 L). The organic phase was separated and washed with H2O (2 x 2 L). The aqueous phase was then extracted with DCM (2 x 1 L). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via silica gel column chromatography eluting with dichloromethane/ethyl acetate (2:1) to afford [(5-bromo-1 - methyl-1 H-imidazol-2-yl)methyl]dimethylamine (int-F1-1). Analytical method 5; tR= 0.60 min; [M+H]+= 220.1.
  • 31
  • [ 79326-88-8 ]
  • 4-chloro-2-(4-(2-((dimethylamino)methyl)-1-methyl-1H-imidazol-5-yl)phenoxy)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: dichloromethane; tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 1.2: 16 h / 0 - 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere 3.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.2: 4 h / 90 °C
Multi-step reaction with 3 steps 1.1: tetrahydrofuran; dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 1.2: 0 - 20 °C / Inert atmosphere 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere 3.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.2: 4 h / 90 °C
  • 32
  • [ 79326-88-8 ]
  • 4-[2-[(dimethylamino)methyl]-1-methyl-1H-imidazol-5-yl]phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dichloromethane; tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 1.2: 16 h / 0 - 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: tetrahydrofuran; dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve 1.2: 0 - 20 °C / Inert atmosphere 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere
  • 33
  • [ 79326-88-8 ]
  • [ 925-90-6 ]
  • 1-(5-bromo-1-methyl-1H-imidazol-2-yl)propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% In tetrahydrofuran at 0 - 20℃; Inert atmosphere; 11.7.1 Step 1.1-(5-Bromo-1-methyl-1H-imidazol-2-yl)propan-1-ol (F68-1) EtMgBr (1 M in THF, 2.08 mL, 2.08 mmol) was added dropwise over 1 minute to a solution of 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (375 mg, 1.984 mmol) in THF (9.9 mL) in a round bottom flask charged with a magnetic stir bar under an atmosphere of N2at 0 °C. The resulting mixture was allowed to warm to rt and stirred overnight. The reaction mixture was then diluted with sat. NH4Cl (25 mL), DCM (100 mL), and H2O (25 mL). The organic phase was separated, and the aqueous layer was washed with DCM (2 x 50 mL). The combined organic phases were dried with Na2SO4, filtered, and concentrated in vacuo to provide a crude yellow oil. The crude oil was purified by silica gel flash chromatography (24 g column, liquid loading (in DCM), eluting with 0-5% MeOH:DCM), but the product-containing fractions contained significant impurities. The fractions were concentrated in vacuo, and the resulting oil was repurified via silica gel flash chromatography (24 g column, liquid loading (in DCM), eluting with 0-50-100% EtOAc:heptane) to provide F68-1 (105 mg, 24% yield) as a colorless oil. Analytical method 5; tR= 0.62 min, [M-H]- = 217.0.
  • 34
  • [ 79326-88-8 ]
  • [ 75-16-1 ]
  • 1-(5-bromo-1-methyl-1H-imidazol-2-yl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
50.7% In tetrahydrofuran; diethyl ether at -78℃; Inert atmosphere; 11.16 Example 11.16: Synthesis of 1-(5-bromo-1-methyl-1H-imidazol-2-yl)ethan-1-ol (F70-1) To a solution of 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (1 g, 5.29 mmol) in anhydrous THF (20 mL) at -78 °C under the presence an atmosphere of nitrogen was added 3 M methylmagnesium bromide in diethyl ether (2.65 mL, 7.94 mmol) dropwise via a syringe. The reaction mixture was stirred at -78 °C for 2 h and then quenched with methanol and sat. NH4Cl. The resulting mixture was extracted with 3 x 40 mL of DCM. The combined organic phases were dried over MgSO4, filtered, and concentrated via rotary evaporation. The formed precipitate was diluted with 2 mL of DCM and filtered to afford the racemic F70-1 (550 mg, 2.68 mmol, 50.7% yield) as a white solid. This racemate was purified by chiral HPLC and F70-1 (260 mg, 1.268 mmol, 24% yield) was obtained (the first peak from chiral separation). Analytical method 5; tR= 0.50 min; [M+H]+= 205.1.
  • 35
  • [ 79326-88-8 ]
  • [ 2065-66-9 ]
  • 5-bromo-1-methyl-2-vinyl-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
28.3% Stage #1: methyl-triphenylphosphonium iodide With potassium hexamethylsilazane In tetrahydrofuran; toluene at 0℃; for 0.5h; Inert atmosphere; Stage #2: 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde In tetrahydrofuran; toluene at 0 - 23℃; 11.15 Example 11.15: Synthesis of 5-bromo-1-methyl-2-vinyl-1H-imidazole (F54-1) To Ph3PCH3I (3.21 g, 7.94 mmol) in anhydrous THF (30 mL) at 0 °C under an atmosphere of nitrogen was added 0.5 M KN(TMS)2in toluene (17.99 mL, 8.99 mmol). The resulting yellow mixture was stirred at 0 °C for 30 min and a solution of 5-bromo-1-methyl-1H-imidazole-2- carbaldehyde (1 g, 5.29 mmol) in anhydrous THF (30 mL) was then added dropwise. The resulting mixture was allowed to warm to rt and stirred overnight. The reaction mixture was quenched with sat. NaHCO3solution and extracted with 2 x 100 mL of EtOAc. The combined organic phases were dried over sodium sulfate, concentrated via rotovap, and purified by silica gel flash chromatography (80 g column, eluting with 0 ^ 100% EtOAc in heptane) to afford F54- 1 (280 mg, 1.497 mmol, 28.3% yield). Analytical method 5; tR= 0.68 min; [M+H]+= 187.0. TLC: Rf=0.35, EtOAc/heptane (1:1).
  • 36
  • [ 79326-88-8 ]
  • (S)-2-((3-(1-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)pyrrolidin-1-yl)methyl)-1-methyl-1H-imidazole-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride; methanol / dichloromethane / 1 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0) / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C / Microwave irradiation
Multi-step reaction with 2 steps 1.1: sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 20 °C 1.2: 0.5 h 2.1: tetrakis(triphenylphosphine) palladium(0) / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C / Microwave irradiation
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); zinc(II) cyanide / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C / Microwave irradiation
  • 37
  • [ 79326-88-8 ]
  • (S)-1-methyl-2-((3-(2-oxo-1-(4-(pyridin-4-yl)phenyl)-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)pyrrolidin-1-yl)methyl)-1H-imidazole-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0) / 1-methyl-pyrrolidin-2-one / 1.5 h / 120 °C / Microwave irradiation
Multi-step reaction with 2 steps 1.1: sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 20 °C 1.2: 0.5 h 2.1: tetrakis(triphenylphosphine) palladium(0) / 1-methyl-pyrrolidin-2-one / 1.5 h / 120 °C / Microwave irradiation
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); zinc(II) cyanide / 1-methyl-pyrrolidin-2-one / 1.5 h / 120 °C / Microwave irradiation
  • 38
  • [ 79326-88-8 ]
  • (S)-1-methyl-2-((3-(2-oxo-1-(4-(pyridin-4-yl)phenyl)-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)pyrrolidin-1-yl)methyl)-1H-imidazole-5-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0) / 1-methyl-pyrrolidin-2-one / 1.5 h / 120 °C / Microwave irradiation 3: hydrogenchloride / water / 1 h / 110 °C / Microwave irradiation
Multi-step reaction with 3 steps 1.1: sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 20 °C 1.2: 0.5 h 2.1: tetrakis(triphenylphosphine) palladium(0) / 1-methyl-pyrrolidin-2-one / 1.5 h / 120 °C / Microwave irradiation 3.1: hydrogenchloride / 1 h / 110 °C / Microwave irradiation 3.2: Cooling with ice
Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); zinc(II) cyanide / 1-methyl-pyrrolidin-2-one / 1.5 h / 120 °C / Microwave irradiation 3: hydrogenchloride / 1 h / 110 °C / Microwave irradiation
  • 39
  • [ 79326-88-8 ]
  • (S)-2-((3-(1-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)pyrrolidin-1-yl)methyl)-1-methyl-1H-imidazole-5-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride; methanol / dichloromethane / 1 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0) / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C / Microwave irradiation 3: hydrogenchloride / water / 1 h / 110 °C / Microwave irradiation
Multi-step reaction with 3 steps 1.1: sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 20 °C 1.2: 0.5 h 2.1: tetrakis(triphenylphosphine) palladium(0) / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C / Microwave irradiation 3.1: hydrogenchloride / 1 h / 110 °C / Microwave irradiation
Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); zinc(II) cyanide / 1-methyl-pyrrolidin-2-one / 1 h / 150 °C / Microwave irradiation 3: hydrogenchloride / 1 h / 110 °C / Microwave irradiation
  • 40
  • [ 79326-88-8 ]
  • (S)-1-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-3-(pyrrolidin-3-yl)-1,3-dihydro-2H-imidazole[4,5-b]pyridine-2-one hydrochloride [ No CAS ]
  • (S)-3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-1-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
286 mg With methanol; sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1h; K-5 (S)-3-(1-((5-Bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-1-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one Example K-5 (S)-3-(1-((5-Bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-1-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one To a mixture of Reference Example F-21 (200 mg), 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (139 mg) and dichloromethane (2 mL) was added NaBH(OAc)3 (415 mg). The reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added methanol (2 mL), and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on amino-silica gel (eluent: n-hexane/ethyl acetate=80/20-0/100) to give the title compound (286mg). MS (ESI_APCI, m/z): 545 (M+H)+
286 mg With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 0.5h; K-5 Example K-5(S) -3- (1-((5-Bromo-1-methyl-1H-imidazol-2-yl) methyl) pyrrolidine-3-yl) -1- (4'-hydroxy- [1,1'- Biphenyl] -4-yl) -1,3-dihydro-2H-imidazole [4,5-b]Pyridine-2-on Reference example F-21 (200mg),5-Bromo-1-methyl-1H-imidazol-2-carbaldehyde (139 mg)) And dichloromethane (2 mL)NaBH (OAc) 3 (415 mg) was added to the mixture of. The reaction mixture was stirred at room temperature for 30 minutes. Methanol (2 mL) was added to the reaction mixture, and the mixture was stirred for 30 minutes. Reaction mixtureThe mixture was concentrated under reduced pressure. The obtained residue was purified by amino silica gel column chromatography (eluting solvent: n-hexane / ethyl acetate = 80/20 to 0/100) to obtain the title compound (286 mg).
  • 41
  • [ 79326-88-8 ]
  • (S)-1-(4-(pyridine-4-yl)phenyl)-3-(pyrrolidine-3-yl)-1,3-dihydro-2H-imidazole[4,5-b]pyridine-2-one hydrochloride [ No CAS ]
  • (S)-3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-1-(4-(pyridin-4-yl)phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
363 mg With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 0.5h; 79 (S)-3-(1-((5-Bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-1-(4-(pyridin-4-yl)phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one Example 79 (S)-3-(1-((5-Bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-1-(4-(pyridin-4-yl)phenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one To a mixture of Reference Example F-22 (285mg), 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (250mg) and dichloromethane (2 mL) was added NaBH(OAc)3 (561mg). The reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added methanol (2 mL), and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on amino-silica gel (eluent: n-hexane/ethyl acetate=80/20-0/100) to give the title compound (363mg).
363 mg Stage #1: 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde; (S)-1-(4-(pyridine-4-yl)phenyl)-3-(pyrrolidine-3-yl)-1,3-dihydro-2H-imidazole[4,5-b]pyridine-2-one hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 0.5h; Stage #2: With methanol In dichloromethane for 0.5h; 79 Example 79 (S) -3- (1-((5-Bromo-1-methyl-1H-imidazol-2-yl) methyl) pyrrolidine-3-yl) -1- (4- (pyridin-4-yl) phenyl) -1,3-dihydro-2H-imidazole [4,5-b] pyridin-2-one Reference example F-22 (285mg),5-Bromo-1-methyl-1H-imidazol-2-carbaldehyde (250 mg)And NaBH (OAc) 3 (561 mg) was added to the mixture of dichloromethane (2 mL).The reaction mixture was stirred at room temperature for 30 minutes.Methanol (2 mL) was added to the reaction mixture, and the mixture was stirred for 30 minutes.The reaction mixture was concentrated under reduced pressure.The obtained residue was purified by amino silica gel column chromatography (eluting solvent: n-hexane / ethyl acetate = 80/20 to 0/100) to give the title compound (363 mg).
363 mg With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 0.5h; 79 Example 79(S) -3- (1-((5-Bromo-1-methyl-1H-imidazol-2-yl) methyl) pyrrolidine-3-yl) -1- (4- (pyridin-4-yl) phenyl) -1,3-dihydro-2H-imidazole [4,5-b] pyridin-2-one Reference example F-22 (285mg),5-Bromo-1-methyl-1H-imidazol-2-carbaldehyde (250 mg)) And dichloromethane (2 mL)NaBH (OAc) 3 (561 mg) was added to the mixture of. The reaction mixture was stirred at room temperature for 30 minutes. Methanol (2 mL) was added to the reaction mixture, and the mixture was stirred for 30 minutes. Reaction mixtureThe mixture was concentrated under reduced pressure. The obtained residue was purified by amino silica gel column chromatography (eluting solvent: n-hexane / ethyl acetate = 80/20 to 0/100) to obtain the title compound (363 mg).
  • 42
  • [ 79326-88-8 ]
  • methyl (S)-4'-(2-oxo-3-(pyrrolidin-3-yl)-2,3-dihydro-1H-imidazole[4,5-b]pyridin-1-yl)-[1,1'-biphenyl]-4-carboxylate hydrochloride [ No CAS ]
  • methyl (S)-4'-(3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidine-3-yl)-2-oxo-2,3-dihydro-1H-imidazole[4,5-b]pyridin-1-yl)-[1,1'-biphenyl]-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
218 mg With methanol; sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1h; K-7 Methyl (S)-4'-(3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)-[1,1'-biphenyl]-4-carboxylate Example K-7 Methyl (S)-4'-(3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)-[1,1'-biphenyl]-4-carboxylate To a mixture of Reference Example F-23 (200 mg), 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (168mg) and dichloromethane (2 mL) was added NaBH(OAc)3 (376mg). The reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added methanol (2 mL), and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on amino-silica gel (eluent: n-hexane/ethyl acetate=80/20-0/100) to give the title compound (218mg). MS (ESI_APCI, m/z): 587 (M+H)+
218 mg With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 0.5h; K-7 Example K-7(S) -4'-(3-(1-((5-Bromo-1-methyl-1H-imidazol-2-yl) methyl) pyrrolidine-3-yl) -2-oxo-2,3-dihydro- 1H-imidazole [4,5-b] pyridin-1-yl)-[1,1'-biphenyl] -4-methyl carboxylate Reference example F-23 (200mg),5-Bromo-1-methyl-1H-imidazol-2-carbaldehyde (168 mg)) And dichloromethane (2 mL)NaBH (OAc) 3 (376 mg) was added to the mixture of.The reaction mixture was stirred at room temperature for 30 minutes. Methanol (2 mL) was added to the reaction mixture, and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by amino silica gel column chromatography (eluting solvent: n-hexane / ethyl acetate = 80/20 to 0/100) to give the title compound (218 mg).
  • 43
  • [ 79326-88-8 ]
  • methyl (S)-2'-hydroxy-4'-(2-oxo-3-(pyrrolidin-3-yl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)-[1,1'-biphenyl]-4-carboxylate hydrochloride [ No CAS ]
  • methyl (S)-4'-(3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)-2'-hydroxy-[1,1'-biphenyl]-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
297 mg With methanol; sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1h; K-9 Methyl (S)-4'-(3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)-2'-hydroxy-[1,1'-biphenyl]-4-carboxylate Example K-9 Methyl (S)-4'-(3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)-2'-hydroxy-[1,1'-biphenyl]-4-carboxylate To a mixture of Reference Example F-26 (200 mg), 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (162mg) and dichloromethane (3 mL) was added NaBH(OAc)3 (363mg). The reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added methanol (3 mL), and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on amino-silica gel (eluent: n-hexane/ethyl acetate/methanol=80/20/0-0/100/0-0/80/20) to give the title compound (297mg). MS (ESI_APCI, m/z): 603 (M+H)+
  • 44
  • [ 79326-88-8 ]
  • methyl (S)-4-(5-(2-oxo-3-(pyrrolidin-3-yl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)pyridin-2-yl)benzoate hydrochloride [ No CAS ]
  • methyl (S)-4-(5-(3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)pyridin-2-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
214 mg With methanol; sodium tris(acetoxy)borohydride In 1-methyl-pyrrolidin-2-one at 20℃; for 1h; K-11 Methyl (S)-4-(5-(3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)pyridin-2-yl)benzoate Example K-11 Methyl (S)-4-(5-(3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)pyridin-2-yl)benzoate To a mixture of Reference Example F-27 (200 mg), 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde (167mg) and dichloromethane (2 mL) was added NaBH(OAc)3 (375 mg). The reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added methanol (2 mL), and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on amino-silica gel (eluent: n-hexane/ethyl acetate=80/20-0/100) to give the title compound (214mg). MS (ESI_APCI, m/z): 588 (M+H)+
  • 45
  • [ 53473-85-1 ]
  • [ 79326-88-8 ]
  • N-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)benzo[d]-isothiazol-5-amine [ No CAS ]
  • 46
  • [ 79326-88-8 ]
  • (S)-1-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-3-(pyrrolidin-3-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one hydrochloride [ No CAS ]
  • (S)-3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidin-3-yl)-1-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
286 mg Stage #1: 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde; (S)-1-(4'-hydroxy-[1,1'-biphenyl]-4-yl)-3-(pyrrolidin-3-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 0.5h; Stage #2: With methanol In dichloromethane for 0.5h; K-5 Example K-5 (S) -3- (1-((5-Bromo-1-methyl-1H-imidazol-2-yl) methyl) pyrrolidine-3-yl) -1- (4'-hydroxy- [1,1'- Biphenyl]-4-yl) -1,3-dihydro-2H-imidazole [4,5-b] pyridin-2-one Reference Example NaBH (OAc) 3 (415 mg) was added to a mixture of F-21 (200 mg), 5-bromo-1-methyl-1H-imidazol-2-carbaldehyde (139 mg) and dichloromethane (2 mL).The reaction mixture was stirred at room temperature for 30 minutes.Methanol (2 mL) was added to the reaction mixture, and the mixture was stirred for 30 minutes.The reaction mixture was concentrated under reduced pressure.The obtained residue was purified by amino silica gel column chromatography (eluting solvent: n-hexane / ethyl acetate = 80/20 to 0/100) to give the title compound (286 mg).
  • 47
  • [ 79326-88-8 ]
  • C24H22N4O3*ClH [ No CAS ]
  • methyl (S)-4'-(3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidine-3-yl)-2-oxo-2,3-dihydro-1H-imidazole[4,5-b]pyridin-1-yl)-[1,1'-biphenyl]-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
218 mg Stage #1: 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde; C24H22N4O3*ClH With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 0.5h; Stage #2: With methanol In dichloromethane for 0.5h; K-7 Example K-7 (S) -4'-(3- (1-((5-Bromo-1-methyl-1H-imidazol-2-yl))Methyl) pyrrolidine-3-yl) -2-oxo-2,3-dihydro-1H-imidazole [4,5-b] pyridin-1-yl)-[1,1'-biphenyl] -4-methyl carboxylate Reference example F-23 (200mg),NaBH (OAc) 3 (376 mg) was added to a mixture of 5-bromo-1-methyl-1H-imidazol-2-carbaldehyde (168 mg) and dichloromethane (2 mL).The reaction mixture was stirred at room temperature for 30 minutes.Methanol (2 mL) was added to the reaction mixture, and the mixture was stirred for 30 minutes.The reaction mixture was concentrated under reduced pressure.The obtained residue was purified by amino silica gel column chromatography (eluting solvent: n-hexane / ethyl acetate = 80/20 to 0/100) to give the title compound (218 mg).
  • 48
  • [ 79326-88-8 ]
  • methyl (S)-2'-hydroxy-4'-(2-oxo-3-(pyrrolidin-3-yl)-2,3-dihydro-1H-imidazole[4,5-b]pyridin-1-yl)-[1,1'-biphenyl]-4-carboxylate hydrochloride [ No CAS ]
  • methyl (S)-4'-(3-(1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidine-3-yl)-2-oxo-2,3-dihydro-1H-imidazole[4,5-b]pyridin-1-yl)-2'-hydroxy-[1,1'-biphenyl]-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
297 mg Stage #1: 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde; methyl (S)-2'-hydroxy-4'-(2-oxo-3-(pyrrolidin-3-yl)-2,3-dihydro-1H-imidazole[4,5-b]pyridin-1-yl)-[1,1'-biphenyl]-4-carboxylate hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 0.5h; Stage #2: With methanol In dichloromethane for 0.5h; K-9 Example K-9 (S) -4'-(3- (1-((5-Bromo-1-methyl-1H-imidazol-2-yl) methyl) pyrrolidine-3-yl) -2-oxo-2,3-dihydro- 1H-imidazole [4,5-b] pyridin-1-yl) -2'-hydroxy- [1,1'-biphenyl] -4-methyl carboxylate Reference example F-26 (200mg),5-Bromo-1-methyl-1H-imidazol-2-carbaldehyde (162 mg)And NaBH (OAc) 3 (363 mg) was added to the mixture of dichloromethane (3 mL).The reaction mixture was stirred at room temperature for 30 minutes.Methanol (3 mL) was added to the reaction mixture, and the mixture was stirred for 30 minutes.The reaction mixture was concentrated under reduced pressure.The obtained residue was purified by amino silica gel column chromatography (eluting solvent: n-hexane / ethyl acetate / methanol = 80/20/0 to 0/100/0 to 0/80/20), and the title compound (297 mg) was purified. ) Was obtained.
297 mg With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 0.5h; K-9 Example K-9(S) -4'-(3-(1-((5-Bromo-1-methyl-1H-imidazol-2-yl) methyl) pyrrolidine-3-yl) -2-oxo-2,3-dihydro- 1H-imidazole [4,5-b] pyridin-1-yl) -2'-hydroxy- [1,1'-biphenyl] -4-methyl carboxylate Reference example F-26 (200 mg), 5-Bromo-1-methyl-1H-imidazol-2-carbaldehyde (162 mg)) And dichloromethane (3 mL) was added with NaBH (OAc) 3 (363 mg). Reaction mixtureThe mixture was stirred at room temperature for 30 minutes. Methanol (3 mL) was added to the reaction mixture, and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by amino silica gel column chromatography (eluting solvent: n-hexane / ethyl acetate / methanol = 80/20/0 to 0/100/0 to 0/80/20)., The title compound (297 mg) was obtained.
  • 49
  • [ 79326-88-8 ]
  • methyl (S)-4-(5-(2-oxo-3-(pyrrolidin-3-yl)-2,3-dihydro-1H-imidazole[4,5-b]pyridin-1-yl)pyridin-2-yl)benzoate hydrochloride [ No CAS ]
  • methyl (S)-4-(5-(3 (1-((5-bromo-1-methyl-1H-imidazol-2-yl)methyl)pyrrolidine-3-yl)-2-oxo-2,3-dihydro-1H-imidazole[4,5-b]pyridin-1-yl)pyridin-2-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
214 mg Stage #1: 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde; methyl (S)-4-(5-(2-oxo-3-(pyrrolidin-3-yl)-2,3-dihydro-1H-imidazole[4,5-b]pyridin-1-yl)pyridin-2-yl)benzoate hydrochloride With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 0.5h; Microwave irradiation; Stage #2: With methanol In dichloromethane for 0.5h; K-11 Example K-11 (S) -4- (5-(3- (1-((5-Bromo-1-methyl-1H-imidazol-2-yl) methyl) pyrrolidine-3-yl) -2-oxo-2,3- Dihydro-1H-imidazole [4,5-b] pyridin-1-yl) pyridin-2-yl) methyl benzoate Reference Example NaBH (OAc) 3 (375 mg) was added to a mixture of F-27 (200 mg), 5-bromo-1-methyl-1H-imidazol-2-carbaldehyde (167 mg) and dichloromethane (2 mL).The reaction mixture was stirred at room temperature for 30 minutes.Methanol (2 mL) was added to the reaction mixture, and the mixture was stirred for 30 minutes.The reaction mixture was concentrated under reduced pressure.The obtained residue was purified by amino silica gel column chromatography (eluting solvent: n-hexane / ethyl acetate = 80/20 to 0/100) to give the title compound (214 mg).
214 mg With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 0.5h; K-11 Example K-11(S) -4- (5-(3- (1-((5-Bromo-1-methyl-1H-imidazol-2-yl) methyl) pyrrolidine-3-yl) -2-oxo-2,3- Dihydro-1H-imidazole [4,5-b] pyridin-1-yl) pyridin-2-yl) methyl benzoate Reference example F-27 (200mg),5-Bromo-1-methyl-1H-imidazol-2-carbaldehyde (167 mg)) And dichloromethane (2 mL)NaBH (OAc) 3 (375 mg) was added to the mixture of.The reaction mixture was stirred at room temperature for 30 minutes. Methanol (2 mL) was added to the reaction mixture, and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by amino silica gel column chromatography (eluting solvent: n-hexane / ethyl acetate = 80/20 to 0/100) to obtain the title compound (214 mg).
  • 50
  • [ 79326-88-8 ]
  • 2-((4-chloro-2-fluorobenzyl)oxy)-6-(piperidin-4-yl)pyridine [ No CAS ]
  • [ 1066-54-2 ]
  • 2-((4-chloro-2-fluorobenzyl)oxy)-6-(1-((1-methyl-5-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)methyl)piperidin-4-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% Stage #1: 5-bromo-1-methyl-1H-imidazole-2-carbaldehyde; trimethylsilylacetylene With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In N,N-dimethyl-formamide at 100℃; Inert atmosphere; Stage #2: 2-((4-chloro-2-fluorobenzyl)oxy)-6-(piperidin-4-yl)pyridine With titanium isopropoxide In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; Stage #3: With sodium tris(acetoxy)borohydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;
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