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[ CAS No. 885522-07-6 ] {[proInfo.proName]}

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Chemical Structure| 885522-07-6
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Product Details of [ 885522-07-6 ]

CAS No. :885522-07-6 MDL No. :MFCD07781604
Formula : C7H4FIN2 Boiling Point : -
Linear Structure Formula :- InChI Key :GSBQTDGAUHVRGU-UHFFFAOYSA-N
M.W : 262.02 Pubchem ID :24728217
Synonyms :

Calculated chemistry of [ 885522-07-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.77
TPSA : 28.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.19
Log Po/w (XLOGP3) : 2.34
Log Po/w (WLOGP) : 2.73
Log Po/w (MLOGP) : 2.73
Log Po/w (SILICOS-IT) : 3.42
Consensus Log Po/w : 2.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.54
Solubility : 0.0748 mg/ml ; 0.000286 mol/l
Class : Soluble
Log S (Ali) : -2.58
Solubility : 0.687 mg/ml ; 0.00262 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.14
Solubility : 0.0189 mg/ml ; 0.0000719 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.28

Safety of [ 885522-07-6 ]

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

Application In Synthesis of [ 885522-07-6 ]

* 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 [ 885522-07-6 ]

[ 885522-07-6 ] Synthesis Path-Downstream   1~85

  • 2
  • [ 348-25-4 ]
  • [ 885522-07-6 ]
YieldReaction ConditionsOperation in experiment
95% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; Intermediate 19: 6-Fluoro-3-iodoindazole; Powdered potassium hydroxide (3.75 eq, 3.93 g, 69 mmol) was added to a solution of 6- fluoroindazole (2.5 g, 18.4 mmol) and iodine (2 eq, 9.35 g, 36.8 mmol) in DMF (45 ml) and the mixture was stirred overnight. The reaction mixture was poured into aqueous sodium thiosulfate solution (10%, 400 ml) and extracted with toluene (x 2). The combined organic phases were washed with water and brine, dried (magnesium sulfate) and concentrated in vacuo to give the title compound as an off-white solid (4.57 g, 95%). HPLC-MS (Method B): MH+ requires m/z=263; Found m/z=263, Rt 1.89 min (99%). 1H NMR (500 MHz, CDC13) delta 6.95 (td, J= 8.9, 2.1 Hz, 1H), 7.12 (d, J = 8.7 Hz, 1H) and 7.41 (dd, J= 8.9, 5.0 Hz, 1 H).
81% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 8h; Example 102.2-(6-Fluoro- 1 -oxetan-3 -yl- 1 H-indazol-3 -yl)-5H-pyrrolo [2,3 -b]pyrazine-7-carboxylic acid isopropylamideStep 16 -Fluoro -3 -iodo - 1 H-indazo leTo a solution of 6-fluoro-l H-indazo le (5.50 g, 40.4 mmol) in DMF (150 ml) at room temperature was added potassium hydroxide ( 6.8 g, 121 mmol) and iodine (15.4 g, 60.6 mmol). The maroon reaction mixture was stirred at room temperature for 8 h then quenched with 10% aqueous Na2S2C"3 and diluted with water. The mixture was extracted with EtOAc (2x). The combined organics were washed with water, sat LiCl, and sat NaCl, then dried over MgS04 andconcentrated to afford 8.6 g (81 >) of 6-fluoro-3 -iodo- 1 H-indazo le as a light yellow solid. 1H NMR (CDCI3, 300 MHz): ? (ppm) 7.48 (dd, J=8.9, 5.1 Hz, 1H), 7.20 (dd, J=8.9, 2.1 Hz, 1H), 7.02 (td, J=9.1 , 2.1 Hz, 1H)
80.34% With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 11h; At room temperature,To a solution of 6-fluoro-lH-indazole (97 mg, 0.71 mmol) in DMF (5 mL)Potassium hydroxide (130 mg, 2.32 mmol)And iodine elemental (280 mg, 1.10 mmol)Stirred at room temperature for 11 h,Saturated sodium thiosulfate solution(10 mL), extracted with ethyl acetate (15 mL x 3), dried over anhydrous sodium sulfate and concentrated column chromatography (petroleum ether / ethyl acetate (v /v = 6/1)Obtain 150 mg of a brown solid in 80.34% yield.
  • 3
  • [ 885522-07-6 ]
  • [ 100-53-8 ]
  • [ 1346560-02-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; ethylene glycol In isopropyl alcohol at 90℃; for 18h; Sealed tube; Intermediate 20: 3-Benzylthio-6-fluoroindazole; A mixture of 6-fluoro-3-iodoindazole (Intermediate 19, 1.88 g, 7.18 mmol), copper(I)iodide (0.13 eq, 0.18 g, 0.93 mmol), ethylene glycol (2 eq, 0.80 ml, 14.4 mmol), benzyl mercaptan (2 eq, 1.70 ml, 14.4 mmol), potassium carbonate (2 eq, 1.99 g, 14.4 mmol) and isopropanol (10 ml) was heated to 90 C in a sealed tube and stirred for 18 hr. After cooling, the mixture was diluted with ethyl acetate and filtered through a pad of celite. The filtrate was concentrated in vacuo to give the title compound, which was used without further purification (4.2 g, »100%). HPLC-MS (Method B): MH+ requires m/z=259; Found m/z=259, Rt 2.13 min (40%).
  • 4
  • [ 885522-07-6 ]
  • [ 1346559-81-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate; ethylene glycol / copper(l) iodide / isopropyl alcohol / 18 h / 90 °C / Sealed tube 2.1: sodium hydrogencarbonate; Oxone / water; acetone / 2 h / 0 - 20 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 4.1: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C 5.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 20 °C 5.2: 20 °C
  • 5
  • [ 885522-07-6 ]
  • [ 1346560-11-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; ethylene glycol / copper(l) iodide / isopropyl alcohol / 18 h / 90 °C / Sealed tube 2: sodium hydrogencarbonate; Oxone / water; acetone / 2 h / 0 - 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 60 °C 4: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C
  • 6
  • [ 885522-07-6 ]
  • [ 1346559-90-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium carbonate; ethylene glycol / copper(l) iodide / isopropyl alcohol / 18 h / 90 °C / Sealed tube 2.1: sodium hydrogencarbonate; Oxone / water; acetone / 2 h / 0 - 20 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 4.1: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C 5.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 20 °C 5.2: 20 °C 6.1: sodium hydride / N,N-dimethyl-formamide; oil / 2 h / 0 - 20 °C 6.2: 24 h
  • 7
  • [ 885522-07-6 ]
  • [ 1346560-05-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; ethylene glycol / copper(l) iodide / isopropyl alcohol / 18 h / 90 °C / Sealed tube 2: sodium hydrogencarbonate; Oxone / water; acetone / 2 h / 0 - 20 °C
  • 8
  • [ 885522-07-6 ]
  • [ 1346560-08-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; ethylene glycol / copper(l) iodide / isopropyl alcohol / 18 h / 90 °C / Sealed tube 2: sodium hydrogencarbonate; Oxone / water; acetone / 2 h / 0 - 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 60 °C
YieldReaction ConditionsOperation in experiment
93% With iodine; sodium hydroxide In methanol at 20℃; for 48h; 47 PREPARATION 30 General procedure: 3-lodo-1H-indazole Iodine (5.8 g, 22.9 mmol) was added in portions over approximately 20 min to a solution of indazole (2.5 g, 21.7 mmol) in methanol (63 ml) and 2N sodium hydroxide solution (65 ml). The mixture remained colourless and a white precipitate slowly formed. The mixture was stirred at room temperature 48 h. The mixture was cooled in an ice-bath and 7.5 ml of concentrated hydrochloric acid was slowly added. The mixture was further acidified with 2N hydrochloric acid. 20% w/v Sodium thiosulfate pentahydrate solution was added until the iodine colour disappeared. The precipitate was filtered, washed with water and dried in the oven at 50 ºC to constant weight. The solid was taken up in methanol, filtered and the filtrated was evaporated under reduced pressure to give 5.0 g (20.6 mmol, 95%) of the title compound as a white solid. Purity 100%.1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.43-7.59 (m, 3H), 7.21-7.26 (m, 1H).UPLC/MS (3 min) retention time 1.56 min.LRMS: m/z 245 (M+1).
93% With iodine; sodium hydroxide In methanol at 20℃; for 48h; 47 PREPARATION 30 3-lodo-1 H-indazole General procedure: Iodine (5.8 g, 22.9 mmol) was added in portions over approximately 20 min to a solution of indazole (2.5 g, 21 .7 mmol) in methanol (63 ml) and 2N sodium hydroxide solution (65 ml). The mixture remained colourless and a white precipitate slowly formed. The mixture was stirred at room temperature 48 h. The mixture was cooled in an ice-bath and 7.5 ml of concentrated hydrochloric acid was slowly added. The mixture was further acidified with 2N hydrochloric acid. 20% w/v Sodium thiosulfate pentahydrate solution was added until the iodine colour disappeared. The precipitate was filtered, washed with water and dried in the oven at 50 °C to constant weight. The solid was taken up in methanol, filtered and the filtrated was evaporated under reduced pressure to give 5.0 g (20.6 mmol, 95%) of the title compound as a white solid. Purity 100%. 1 H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.43-7.59 (m, 3H), 7.21 -7.26 (m, 1 H). UPLC/MS (3 min) retention time 1 .56 min. LRMS: m/z 245 (M+1 ).
  • 10
  • [ 885522-07-6 ]
  • [ 1422772-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 2 h / 90 °C / Inert atmosphere
  • 11
  • [ 885522-07-6 ]
  • [ 1422772-58-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 80 °C / Inert atmosphere
  • 12
  • [ 885522-07-6 ]
  • [ 1422772-12-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 80 °C / Inert atmosphere 4.1: aminosulfonic acid / 1,4-dioxane; water / 0.17 h / 20 °C / Cooling with ice 4.2: 20 h 5.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 13
  • [ 885522-07-6 ]
  • 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-methyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 80 °C / Inert atmosphere 4.1: aminosulfonic acid / 1,4-dioxane; water / 0.17 h / 20 °C / Cooling with ice 4.2: 20 h
  • 14
  • [ 885522-07-6 ]
  • [ 1422772-61-9 ]
  • [ 1422772-60-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 80 °C / Inert atmosphere 4.1: aminosulfonic acid / 1,4-dioxane; water / 0.17 h / 20 °C / Cooling with ice 4.2: 20 h 5.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C
  • 15
  • [ 885522-07-6 ]
  • [ 1422772-81-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere
  • 16
  • [ 885522-07-6 ]
  • [ 1422772-82-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 4.1: potassium hydroxide / 1,4-dioxane; water / 5 h / 100 °C
  • 17
  • [ 885522-07-6 ]
  • [ 1426424-98-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 4.1: potassium hydroxide / 1,4-dioxane; water / 5 h / 100 °C 5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 16 h / 20 °C
  • 18
  • [ 885522-07-6 ]
  • [ 1426425-16-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 4.1: potassium hydroxide / 1,4-dioxane; water / 5 h / 100 °C 5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 16 h / 20 °C
  • 19
  • [ 885522-07-6 ]
  • [ 1422772-86-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 4.1: potassium hydroxide / 1,4-dioxane; water / 5 h / 100 °C 5.1: dmap; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 6 h / 20 °C
  • 20
  • [ 885522-07-6 ]
  • [ 1422772-18-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 4.1: potassium hydroxide / 1,4-dioxane; water / 5 h / 100 °C 5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 16 h / 20 °C 6.1: hydrogenchloride / 1,4-dioxane; water / 16 h / 20 °C
  • 21
  • [ 885522-07-6 ]
  • [ 1426420-07-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 4.1: potassium hydroxide / 1,4-dioxane; water / 5 h / 100 °C 5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 16 h / 20 °C 6.1: hydrogenchloride / 1,4-dioxane; water / 2 h / 20 °C
  • 22
  • [ 885522-07-6 ]
  • [ 1422772-20-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 4.1: potassium hydroxide / 1,4-dioxane; water / 5 h / 100 °C 5.1: dmap; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 6 h / 20 °C 6.1: hydrogenchloride / 1,4-dioxane; water / 3 h
  • 23
  • [ 885522-07-6 ]
  • [ 1426425-39-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 4.1: potassium hydroxide / 1,4-dioxane; water / 5 h / 100 °C 5.1: dmap; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / 20 °C
  • 25
  • [ 885522-07-6 ]
  • [ 1426425-83-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 85 °C / Inert atmosphere; Sonication 3.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 65 °C
  • 27
  • [ 885522-07-6 ]
  • [ 1426425-94-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 85 °C / Sonication 3.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 65 °C
  • 28
  • [ 885522-07-6 ]
  • [ 1426425-95-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 85 °C / Sonication 3.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 65 °C 4.1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C
  • 29
  • [ 885522-07-6 ]
  • [ 1422772-26-6 ]
  • [ 1422772-24-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 4.1: potassium hydroxide / 1,4-dioxane; water / 5 h / 100 °C 5.1: dmap; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 20 °C
  • 30
  • [ 885522-07-6 ]
  • [ 1426425-82-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 85 °C / Inert atmosphere; Sonication 3.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 65 °C
  • 31
  • [ 885522-07-6 ]
  • [ 1426425-97-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 85 °C / Sonication 3.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 40 °C
  • 32
  • [ 885522-07-6 ]
  • [ 1422773-10-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C 1.2: 0.5 h / -10 °C 1.3: 3.33 h / -10 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere
  • 33
  • [ 885522-07-6 ]
  • [ 1422773-11-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere; Microwave irradiation
  • 34
  • [ 885522-07-6 ]
  • [ 1422773-12-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere; Microwave irradiation 4.1: sodium hydrogencarbonate; aminosulfonic acid; sodium chlorite / water; tetrahydrofuran / 1.5 h / 20 °C
  • 35
  • [ 885522-07-6 ]
  • [ 1422773-13-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere; Microwave irradiation 4.1: sodium hydrogencarbonate; aminosulfonic acid; sodium chlorite / water; tetrahydrofuran / 1.5 h / 20 °C 5.1: HATU / N,N-dimethyl-formamide / 20 °C
  • 36
  • [ 885522-07-6 ]
  • [ 1422772-34-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 85 °C / Inert atmosphere; Sonication 3.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 65 °C 4.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 37
  • [ 885522-07-6 ]
  • [ 1422772-35-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 85 °C / Sonication 3.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 65 °C 4.1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C 5.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 38
  • [ 885522-07-6 ]
  • [ 1422772-36-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 16 h / 85 °C / Inert atmosphere; Sonication 3.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 65 °C 4.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 39
  • [ 885522-07-6 ]
  • [ 1422772-37-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4 h / 85 °C / Sonication 3.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 40 °C 4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 40
  • [ 885522-07-6 ]
  • [ 1422772-39-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 20 °C 1.2: 1 h / -10 °C 1.3: 3.33 h / -10 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere; Microwave irradiation 4.1: sodium hydrogencarbonate; aminosulfonic acid; sodium chlorite / water; tetrahydrofuran / 1.5 h / 20 °C 5.1: HATU / N,N-dimethyl-formamide / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 41
  • [ 885522-07-6 ]
  • [ 1422772-09-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 2 h / 90 °C / Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 3 h
  • 42
  • [ 885522-07-6 ]
  • [ 1426427-09-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 5 h / 0 - 20 °C 2.1: sodium chloride; isopropylmagnesium chloride / tetrahydrofuran / -16 °C 2.2: 2.5 h / -16 - 20 °C / Enzymatic reaction
Multi-step reaction with 3 steps 1: potassium <i>tert</i>-butylate / 0 - 20 °C 2: isopropyl magnesium chloride / tetrahydrofuran / -10 °C 3: tetrahydrofuran / -10 - 20 °C
Multi-step reaction with 2 steps 1.1: caesium carbonate / dimethyl sulfoxide / 1.5 h / 20 °C 2.1: isopropylmagnesium bromide / tetrahydrofuran / 0.33 h / -16 °C 2.2: 5 h / 20 °C
  • 43
  • [ 885522-07-6 ]
  • [ 74-88-4 ]
  • [ 1257535-15-1 ]
YieldReaction ConditionsOperation in experiment
99% With caesium carbonate In dimethyl sulfoxide at 20℃; for 1.5h; 49.2 Step 2: Synthesis of compound 6-fluoro-3-iodo-1-methyl-1H-indazole At room temperature,To a solution of 6-fluoro-3-iodo-lH-indazole (97 mg, 0.37 mmol)In DMSO (5 mL)Cesium carbonate (60 mg, 0.18 mmol)And methyl iodide (70 [mu] L, 0.76 mmol)Stirred at room temperature for 1.5 hours,Add water (10mL) quenching, B(15 mL x3), dried over anhydrous sodium sulfate, and concentrated column chromatography (petroleum ether / ethyl acetate (v / v) = 6/1)100 mg of a yellow solid was obtained in a yield of 99%.
68% Stage #1: 6-fluoro-3-iodo-1H-indazole With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 5h;
With potassium <i>tert</i>-butylate at 0 - 20℃;
  • 44
  • [ 885522-07-6 ]
  • [ 1461-22-9 ]
  • [ 1422773-02-1 ]
YieldReaction ConditionsOperation in experiment
47% Stage #1: 6-fluoro-3-iodo-1H-indazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.166667h; Stage #2: With isopropylmagnesium chloride In tetrahydrofuran; mineral oil at -10℃; for 1h; Stage #3: tributyltin chloride In tetrahydrofuran at -10℃; for 3.33333h;
47% Stage #1: 6-fluoro-3-iodo-1H-indazole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Stage #2: With isopropylmagnesium chloride In tetrahydrofuran; mineral oil at -10℃; for 0.5h; Stage #3: tributyltin chloride In tetrahydrofuran; mineral oil at -10 - 20℃; for 3.33333h; 102.2 Step 26-Fluoro-3 -tributylstannanyl- 1 H-indazole Step 26-Fluoro-3 -tributylstannanyl- 1 H-indazoleTo a solution of 6-fluoro-3-iodo-l H-indazole (8.6 g, 32.8 mmol) in THF (200 mL) at 0°C was slowly added portionwise sodium hydride (60% in mineral oil, 1.58 g, 39.4 mmol). The reaction mixture was stirred at room temperature for 10 min then cooled to -10°C andisopropylmagnesium chloride (2.0 M in THF, 19.7 mL, 39.4 mmol) was added. The reaction mixture was stirred at -10°C for 30 min then additional isopropylmagnesium chloride (2.0 M in THF, 8.2 mL, 16.4 mmol) was added. The reaction mixture was stirred at -10°C for 30 min then tributylchlorostannane (11.6 mL, 42.7 mmol) was slowly added. Stirring was continued at -10°C for 20 min then at room temperature for 3 h. The reaction mixture was quenched with saturated aqueous NH4CI then diluted with water and extracted with EtOAc (2x). The combined organics were washed with brine then dried over MgSC^ and concentrated. The residue was purified by silica gel chromatography with 10% to 20% EtO Ac/heptane (0.5% Et3N) to afford 6.53 g (47%) of 6-fluoro-3 -tributylstannanyl- 1 H-indazole as a light brown viscous oil. 'H NMR (CDC13, 300 MHz): ? (ppm) 7.65 (dd, J=8.7, 5.3 Hz, 1H), 7.20 (dd, J=9.3, 2.1 Hz, 1H), 6.92 (td, J=9.0, 2.1 Hz, 1H), 1.53 - 1.67 (m, 6H), 1.28 - 1.43 (m, 6H), 1.20 - 1.28 (m, 6H), 0.89 (t, J=7.4 Hz, 9H).
  • 45
  • [ 885522-07-6 ]
  • [ 1426417-12-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C 1.2: 0.5 h / -10 °C 1.3: 3.33 h / -10 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Microwave irradiation; Sealed tube 4.1: aminosulfonic acid; sodium chlorite; potassium dihydrogenphosphate / 1,4-dioxane; water / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C 6.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
  • 46
  • [ 885522-07-6 ]
  • [ 1426422-27-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C 1.2: 0.5 h / -10 °C 1.3: 3.33 h / -10 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Microwave irradiation; Sealed tube
  • 47
  • [ 885522-07-6 ]
  • [ 1426422-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C 1.2: 0.5 h / -10 °C 1.3: 3.33 h / -10 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Microwave irradiation; Sealed tube 4.1: aminosulfonic acid; sodium chlorite; potassium dihydrogenphosphate / 1,4-dioxane; water / 0 - 20 °C
  • 48
  • [ 885522-07-6 ]
  • [ 1426422-29-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C 1.2: 0.5 h / -10 °C 1.3: 3.33 h / -10 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Microwave irradiation; Sealed tube 4.1: aminosulfonic acid; sodium chlorite; potassium dihydrogenphosphate / 1,4-dioxane; water / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C
  • 49
  • [ 885522-07-6 ]
  • [ 1426417-14-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C 1.2: 0.5 h / -10 °C 1.3: 3.33 h / -10 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 3 h / 100 °C / Microwave irradiation; Sealed tube 4.1: aminosulfonic acid; sodium chlorite; potassium dihydrogenphosphate / 1,4-dioxane; water / 0 - 20 °C 5.1: HATU / N,N-dimethyl-formamide / 20 °C 6.1: palladium 10% on activated carbon; ammonium formate / tetrahydrofuran; methanol / 20 - 50 °C / Sealed tube 7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 7.2: 1 h / 20 °C
  • 50
  • [ 885522-07-6 ]
  • [ 1426422-30-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C 1.2: 0.5 h / -10 °C 1.3: 3.33 h / -10 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 3 h / 100 °C / Microwave irradiation; Sealed tube
  • 51
  • [ 885522-07-6 ]
  • [ 1426422-31-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C 1.2: 0.5 h / -10 °C 1.3: 3.33 h / -10 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 3 h / 100 °C / Microwave irradiation; Sealed tube 4.1: aminosulfonic acid; sodium chlorite; potassium dihydrogenphosphate / 1,4-dioxane; water / 0 - 20 °C
  • 52
  • [ 885522-07-6 ]
  • [ 1426422-32-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C 1.2: 0.5 h / -10 °C 1.3: 3.33 h / -10 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 3 h / 100 °C / Microwave irradiation; Sealed tube 4.1: aminosulfonic acid; sodium chlorite; potassium dihydrogenphosphate / 1,4-dioxane; water / 0 - 20 °C 5.1: HATU / N,N-dimethyl-formamide / 20 °C
  • 53
  • [ 885522-07-6 ]
  • [ 1426422-33-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C 1.2: 0.5 h / -10 °C 1.3: 3.33 h / -10 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 3 h / 100 °C / Microwave irradiation; Sealed tube 4.1: aminosulfonic acid; sodium chlorite; potassium dihydrogenphosphate / 1,4-dioxane; water / 0 - 20 °C 5.1: HATU / N,N-dimethyl-formamide / 20 °C 6.1: palladium 10% on activated carbon; ammonium formate / tetrahydrofuran; methanol / 20 - 50 °C / Sealed tube
  • 54
  • [ 885522-07-6 ]
  • C29H34FN7O3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium <i>tert</i>-butylate / 0 - 20 °C 2: isopropyl magnesium chloride / tetrahydrofuran / -10 °C 3: tetrahydrofuran / -10 - 20 °C 4: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 2 h / 85 °C
  • 55
  • [ 885522-07-6 ]
  • C23H20FN7O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium <i>tert</i>-butylate / 0 - 20 °C 2: isopropyl magnesium chloride / tetrahydrofuran / -10 °C 3: tetrahydrofuran / -10 - 20 °C 4: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 2 h / 85 °C 5: trifluoroacetic acid / dichloromethane
  • 56
  • [ 885522-07-6 ]
  • C8H6FMgN2(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / 0 - 20 °C 2: isopropyl magnesium chloride / tetrahydrofuran / -10 °C
  • 57
  • [ 885522-07-6 ]
  • [ 501938-98-3 ]
  • methyl [3-(6-fluoro-3-iodo-1H-indazol-1-yl)propyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
836 mg With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 72h; 102.1 (1) To a solution of 6-fluoro-3-iodo-1H-indazole (1.5 g) and methyl (3-bromopropyl)carbamate (1.68 g) in N,N-dimethylformamide (5 mE) was addedpotassium carbonate (1.58 g), and the mixture was stirred at room temperature for 3 days. To the reaction solution was added ethyl acetate, and the mixture was washed with aqueous saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/20-3/2) to give methyl [3-(6-fluoro-3-iodo-1H- indazol-1-yl)propyl]carbamate [REx(102-1)] (836 mg) as a red oil.10398] APCI-MS mlz: 378 [M+H].
  • 58
  • [ 885522-07-6 ]
  • [ 501938-98-3 ]
  • methyl [3-(3-acetyl-6-fluoro-1H-indazol-1-yl)propyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 72 h / 20 °C 2.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 17 h / Reflux 2.2: 0.25 h / 20 °C 2.3: 1 h / 20 °C
  • 59
  • [ 885522-07-6 ]
  • [ 5122-95-2 ]
  • C19H13FN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate In 1,4-dioxane; water at 100℃; for 16h; 1 (1114) To the iodo compound 110 (78 mg, 0.30 mmol), in dioxanewater (31 ml), 3-biphenylboronic acid (71 mg, 0.36 mmol), sodium acetate (117 mg, 1.42 mmol) and PdCl2(dppf) (44 mg, 0.06 mmol) were added. Then the reaction mixture was heated to 100° C. for 16 h. Then reaction mixture was cooled and diluted with ethyl acetate. Organic layer was separated and washed with water, brine and dried. Crude residue was column chromatographed to yield 113 in 65% yield. (1115) 1H NMR (CDCl3): 10.87 (br s, 1H), 8.17 (s, 1H), 8.00-7.91 (m, 2H), 7.68-7.46 (m, 4H), 7.49-7.25 (m, 3H), 7.02-6.97 (m, 2H). (1116) Mass spectrum (ESI+): m/z=289 [M+1].
  • 60
  • [ 885522-07-6 ]
  • [ 13922-41-3 ]
  • C17H11FN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate In 1,4-dioxane; water at 100℃; for 16h; 1 (1111) To the iodo compound 110 (78 mg, 0.30 mmol), in dioxanewater (31 ml), naphthylboronic acid (62 mg, 0.36 mmol), sodium acetate (117 mg, 1.42 mmol) and PdCl2(dppf) (44 mg, 0.06 mmol) were added. Then the reaction mixture was heated to 100° C. for 16 h. Then reaction mixture was cooled and diluted with ethyl acetate. Organic layer was separated and washed with water, brine and dried. Crude residue was column chromatographed to yield 112 in 64% yield. (1112) 1H NMR (CDCl3): 8.38 (s, 1H), 8.10-7.89 (m, 5H), 7.54-7.52 (d, 2H, J=6 Hz), 7.21-7.18 (d, 1H, j=6 Hz), 7.04-7.01 (t, 2H, j=6 Hz). (1113) Mass spectrum (ESI+): m/z=263 [M+1].
  • 61
  • [ 885522-07-6 ]
  • [ 1423-26-3 ]
  • C14H8F4N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate In 1,4-dioxane; water at 100℃; for 16h; 1 (1108) To the iodo compound 110 (78 mg, 0.30 mmol), in dioxanewater (31 ml), 3(trifluoromethyl)phenylboronic acid (68 mg, 0.36 mmol), sodium acetate (117 mg, 1.42 mmol) and PdCl2(dppf) (44 mg, 0.06 mmol) were added. Then the reaction mixture was heated to 100° C. for 16 h. Then reaction mixture was cooled and diluted with ethyl acetate. Organic layer was separated and washed with water, brine and dried. Crude residue was column chromatographed to yield 111 in 72% yield. (1109) 1H NMR (CDCl3): 10.41 (br s, 1H), 8.1 (s, 1H), 8.14-8.12 (d, 1H, J=6 Hz), 7.96-7.92 (m, 1H), 7.70-7.61 (m, 2H), 7.16-7.13 (d, 1H, J=6 Hz), 7.05-7.02 (t, 1H, j=6 Hz). (1110) Mass spectrum (ESI+): m/z=281 [M+1].
  • 62
  • [ 885522-07-6 ]
  • [ 89598-96-9 ]
  • C13H8BrFN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate In 1,4-dioxane; water at 100℃; for 16h; 1 (1129) To the iodo compound 110 (400 mg, 1.53 mmol), in dioxanewater (103 ml), 3-bromophenylboronic acid (369 mg, 1.83 mmol), sodium acetate (591 mg, 7.20 mmol) and PdCl2(dppf) (224 mg, 0.31 mmol) were added. Then the reaction mixture was heated to 100° C. for 16 h. Then reaction mixture was cooled and diluted with ethyl acetate. Organic layer was separated and washed with water, brine and dried. Crude residue was column chromatographed to yield 119 in 15% yield. (1130) Mass spectrum (ESI+): m/z=291 [M+1].
  • 63
  • [ 885522-07-6 ]
  • [ 89598-96-9 ]
  • C19H12ClFN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 16 h / 100 °C 2: sodium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 16 h / 100 °C
  • 64
  • [ 885522-07-6 ]
  • 3-((3-(2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)phenyl)amino)propanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / dimethyl sulfoxide / 1.5 h / 20 °C 2.1: isopropylmagnesium bromide / tetrahydrofuran / 0.33 h / -16 °C 2.2: 5 h / 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 4.5 h / 90 °C / Inert atmosphere
  • 65
  • [ 446-48-0 ]
  • [ 885522-07-6 ]
  • 6-fluoro-1-(2-fluorobenzyl)-3-iodo-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.706 g With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; 5.3 Step 3: 6-fluoro-1-(2-fluorobenzyl)-3-iodo-1H-indazole 6-Fluoro-3-iodo-1H-indazole (500 mg, 1.91 mmol) was added into a 50 mL flask, thenN,N-dimethylformamide (1 0 mL ), 1-(bromomethyl)-2-fluorobenzene (399 mg, 2.11 mmol) andcesium carbonate (688 mg, 2.11 mmol) were added. The mixture was stirred for 2 h at roomtemperature. The reaction mixture was extracted with ethyl acetate (60 mL x 3). The combinedorganic layers were washed with water (100 mL x 3) and saturated brine (100 mL x 2), driedover anhydrous sodium sulfate, filtered, and the filtrate was concentrated in vacuo to give thetitle compound as brownish black oil (0.706 g, 99.9%).MS (ESI, pos. ion) m/z: 371.0 (M+ 1).
  • 66
  • [ 885522-07-6 ]
  • 3-(bromomethyl)pyridine hydrobromide [ No CAS ]
  • 6-fluoro-3-iodo-1-(pyridin-3-ylmethyl)-1H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
69.9% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; 7.1 Step 1: 6-fluoro-3-iodo-1-(pyridin-3-ylmethyl)-1H-indazole To a 250 mL two-neck flask were added 6-fluoro-3-iodo-1H-indazole (7.51 g, 28.7mmol), N,N-dimethylformamide (113 mL), cesium carbonate (19.7 g, 60.5 mmol) and3-(bromomethyl)pyridine hydrobromide (7.94 g, 31.4 mmol). The mixture was stirred for 2 h atroom temperature. The reaction mixture was poured into ice-water (500 mL), and the resultingmixture was extracted with ethyl acetate (100 mL x 3). The combined organic layers werewashed with water (200 mL x 2) and saturated brine (100 mL), dried over anhydrous sodiumsulfate and filtered. The filtrate was concentrated on a rotary evaporator to give a yellow solid(7.07 g, 69.9%).MS (ESI, pos. ion) m/z: 354.05 (M+ 1).
  • 67
  • [ 3939-09-1 ]
  • [ 885522-07-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / butan-1-ol / 17 h / 150 °C / Inert atmosphere 2.1: boron trifluoride diethyl etherate; isopentyl nitrite / tetrahydrofuran / 0.5 h / -10 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice
  • 68
  • [ 404827-75-4 ]
  • [ 885522-07-6 ]
YieldReaction ConditionsOperation in experiment
6-Fluoro-1H-indazol-3-amine (4.85 g, 32.1 mmol) was dissolved in tetrahydrofuran(50 mL), then boron trifluoride diethyl etherate (8.0 mL, 64.8 mmol) was added dropwise slowlyunder an ice-bath condition. After the addition, then the reaction flask was placed in acircumstance of -10 C, then a solution of isoamyl nitrite (5.6 mL, 42.0 mmol) in tetrahydrofuran(20 mL) was added dropwise slowly. After the addition, the reaction mixture was stirred for 30min. Ethyl ether (100 mL) was added to precipitate the solid product, and the mixture wasfiltered by suction to give a black brown solid. The solid then was dissolved in acetone (120 mL),and sodium iodide (6.25 g, 41.7 mmol) was added under an ice-bath condition, and the resultingmixture was stirred at rt for 30 minutes. The reaction mixture was extracted with ethyl acetate(100 mL x 3), and the combined organic layers were washed with water (200 mL x 2) andsaturated brine (150 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to remove the solvent to give a brownish black solid, which was used in the next step withoutfurther purification.MS (ESI, pos. ion) m/z: 263.0 (M+ 1).
  • 69
  • [ 885522-07-6 ]
  • 6-fluoro-1-(2-fluorobenzyl)-1H-indazole-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2: dimethyl sulfoxide / 3 h / 150 °C
  • 70
  • [ 885522-07-6 ]
  • 6-fluoro-1-(2-fluorobenzyl)-1H-indazole-3-carboximidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: dimethyl sulfoxide / 3 h / 150 °C 3.1: sodium methylate / methanol / 2 h / 20 °C 3.2: 4 h / 75 °C
  • 71
  • [ 885522-07-6 ]
  • 2-(6-fluoro-1-(2-fluorobenzyl)-1H-indazol-3-yl)-5-(phenyldiazenyl)pyrimidine-4,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: dimethyl sulfoxide / 3 h / 150 °C 3.1: sodium methylate / methanol / 2 h / 20 °C 3.2: 4 h / 75 °C 4.1: triethylamine / N,N-dimethyl-formamide / 85 - 100 °C
  • 72
  • [ 885522-07-6 ]
  • 2-(6-fluoro-1-(2-fluorobenzyl)-1H-indazol-3-yl)pyrimidine-4,5,6-triamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: dimethyl sulfoxide / 3 h / 150 °C 3.1: sodium methylate / methanol / 2 h / 20 °C 3.2: 4 h / 75 °C 4.1: triethylamine / N,N-dimethyl-formamide / 85 - 100 °C 5.1: palladium 10% on activated carbon; hydrogen / 20 °C
  • 73
  • [ 885522-07-6 ]
  • methyl (4,6-diamino-2-(6-fluoro-1-(2-fluorobenzyl)-1H-indazol-3-yl)pyrimidin-5-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: dimethyl sulfoxide / 3 h / 150 °C 3.1: sodium methylate / methanol / 2 h / 20 °C 3.2: 4 h / 75 °C 4.1: triethylamine / N,N-dimethyl-formamide / 85 - 100 °C 5.1: palladium 10% on activated carbon; hydrogen / 20 °C 6.1: pyridine / 10 h / Cooling with ice
  • 74
  • [ 885522-07-6 ]
  • methyl (4,6-diamino-2-(6-fluoro-1-(2-fluorobenzyl)-1H-indazol-3-yl)pyrimidin-5-yl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: dimethyl sulfoxide / 3 h / 150 °C 3.1: sodium methylate / methanol / 2 h / 20 °C 3.2: 4 h / 75 °C 4.1: triethylamine / N,N-dimethyl-formamide / 85 - 100 °C 5.1: palladium 10% on activated carbon; hydrogen / 20 °C 6.1: pyridine / 10 h / Cooling with ice 7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 20 °C / Cooling with ice
  • 75
  • [ 885522-07-6 ]
  • 6-fluoro-1-(pyridin-3-ylmethyl)-1H-indazole-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2: dimethyl sulfoxide / 2 h / 150 °C
  • 76
  • [ 885522-07-6 ]
  • 6-fluoro-1-(pyridin-3-ylmethyl)-1H-indazole-3-carboximidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: dimethyl sulfoxide / 2 h / 150 °C 3.1: sodium methylate / methanol / 3 h / 20 °C 3.2: Reflux
  • 77
  • [ 885522-07-6 ]
  • 2-(6-fluoro-1-(pyridin-3-ylmethyl)-1H-indazol-3-yl)-5-(phenyldiazenyl)pyrimidine-4,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: dimethyl sulfoxide / 2 h / 150 °C 3.1: sodium methylate / methanol / 3 h / 20 °C 3.2: Reflux 4.1: triethylamine / 5 h / 85 - 100 °C / Inert atmosphere
  • 78
  • [ 885522-07-6 ]
  • 2-(6-fluoro-1-(pyridin-3-ylmethyl)-1H-indazol-3-yl)pyrimidine-4,5,6-triamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: dimethyl sulfoxide / 2 h / 150 °C 3.1: sodium methylate / methanol / 3 h / 20 °C 3.2: Reflux 4.1: triethylamine / 5 h / 85 - 100 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / N,N-dimethyl-formamide / 20 °C
  • 79
  • [ 885522-07-6 ]
  • methyl (4,6-diamino-2-(6-fluoro-1-(pyridin-3-ylmethyl)-1H-indazol-3-yl)pyrimidin-5-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: dimethyl sulfoxide / 2 h / 150 °C 3.1: sodium methylate / methanol / 3 h / 20 °C 3.2: Reflux 4.1: triethylamine / 5 h / 85 - 100 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / N,N-dimethyl-formamide / 20 °C 6.1: pyridine / dichloromethane / 2 h / 0 °C
  • 80
  • [ 885522-07-6 ]
  • methyl (4,6-diamino-2-(6-fluoro-1-(pyridin-3-ylmethyl)-1H-indazol-3-yl)pyrimidin-5-yl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: dimethyl sulfoxide / 2 h / 150 °C 3.1: sodium methylate / methanol / 3 h / 20 °C 3.2: Reflux 4.1: triethylamine / 5 h / 85 - 100 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C 5.2: 1.5 h / 0 - 20 °C
  • 81
  • [ 885522-07-6 ]
  • 2-(6-fluoro-1-(2-fluorobenzyl)-1H-indazol-3-yl)-N<SUP>5</SUP>-(tetrahydrofuran-3-yl)pyrimidine-4,5,6-triamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: dimethyl sulfoxide / 3 h / 150 °C 3.1: sodium methylate / methanol / 2 h / 20 °C 3.2: 4 h / 75 °C 4.1: triethylamine / N,N-dimethyl-formamide / 85 - 100 °C 5.1: palladium 10% on activated carbon; hydrogen / 20 °C 6.1: acetic acid / methanol / 1 h / 20 °C / Cooling with ice 6.2: 20 °C
  • 82
  • [ 885522-07-6 ]
  • tert-butyl 6-fluoro-3-(4-(methoxycarbonyl)phenyl)-1H-indazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; toluene; ethanol / 16 h / 75 °C / Inert atmosphere
  • 83
  • [ 885522-07-6 ]
  • 3-(2H-1,3-benzodioxol-5-yl)-6-fluoro-2H-indazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; toluene; ethanol / 16 h / 75 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 16 h / 20 °C
  • 84
  • [ 885522-07-6 ]
  • tert-butyl 3-(benzo[d][1,3]dioxol-5-yl)-6-fluoro-1H-indazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; toluene; ethanol / 16 h / 75 °C / Inert atmosphere
  • 85
  • [ 885522-07-6 ]
  • 4-(6-fluoro-2H-indazol-3-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; toluene; ethanol / 16 h / 75 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 16 h / 20 °C 4: water; sodium hydroxide / methanol; tetrahydrofuran / 16 h / 20 °C
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