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[ CAS No. 1029438-36-5 ]

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Chemical Structure| 1029438-36-5
Chemical Structure| 1029438-36-5
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Product Details of [ 1029438-36-5 ]

CAS No. :1029438-36-5 MDL No. :MFCD14636485
Formula : C12H10BFO3 Boiling Point : 373.7±52.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :232.02 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1029438-36-5 ]

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
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Application In Synthesis of [ 1029438-36-5 ]

  • Downstream synthetic route of [ 1029438-36-5 ]

[ 1029438-36-5 ] Synthesis Path-Downstream   1~12

  • 2
  • [ 1029438-36-5 ]
  • [ 1272668-50-4 ]
  • [ 1610698-01-5 ]
YieldReaction ConditionsOperation in experiment
66% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water; acetonitrile at 90℃; Inert atmosphere; 22 General procedure: A mixture of (R)-tert-butyl 3-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate (1) (2.0 g, 4.66 mmol), 4-phenoxyphenylboronic acid (1.3 g, 6.06 mmol), Pd(dppf)Cl2 (190 mg, 0.23 mmol) and Na2CO3 (1.9 g, 14.0 mmol) in DME (35.0 mL) and H2O (15.0 mL) was heated at 90° C. under N2 atmosphere overnight. After cooled down to r. t., the reaction mixture was diluted with water (50.0 mL) and DCM (50.0 mL). The layers were separated and the aqueous phase was extracted with DCM (25 mL*1). Combined organic phases were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to obtain the crude product which was purified by column chromatographic (silica gel, 0-80% ethyl acetate in petroleum ether ("PE") with DCM (1:1)) to afford (R)-tert-butyl-3-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate (2) (1.3 g, 60% yield) as a yellow solid. 11174] In a similar manner as described in Example 1, (R)-tert-butyl 3-(4-amino-5-(4-(3-fluorophenoxy)phenyl)- 7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine- 1 -carboxylate (50) (604 mg, 66%) was obtained as a light yellow solid from (R)-tert-butyl 3-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimi- din-7-yl)pyrrolidine-1 -carboxylate (1) (800 mg, 1.9 mmol) and 4-(3-fluorophenoxy)phenylboronic acid (400 mg, 1.7 mmol). LC-MS (ESI): mlz (M+1) 490.2.
  • 3
  • [ 3934-20-1 ]
  • [ 1029438-36-5 ]
  • C16H10ClFN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In acetonitrile at 90℃; for 4h;
  • 4
  • [ 1029438-36-5 ]
  • 4-((4-(4-(3-fluorophenoxy)phenyl)pyrimidin-2-yl)amino)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / acetonitrile / 4 h / 90 °C 2: hydrogenchloride / ethanol / 2 h / 160 °C / Microwave irradiation
  • 6
  • [ 5419-55-6 ]
  • 1-(4-bromophenoxy)-3-fluorobenzene [ No CAS ]
  • [ 1029438-36-5 ]
YieldReaction ConditionsOperation in experiment
50% With n-butyllithium In tetrahydrofuran; diethyl ether at -70℃; for 5h; 15.4 Step 4: (4-(3-fluorophenoxy)phenyl)boric acid To a dried 25 mL three-necked-flask was added 100 mL ultra dry THF and 1-(4-bromophenoxy)-3-fluorobenzene(2.00 g, 7.49 mmol). The flask was then cooled to - 70°C in dry ice-ethanol bath. N-butyl lithium ether solution (1.6 M,9.73 mmol) was slowly added into the mixture, and the resulting solution was continued to react at the same temperature.The reacting solution was added with triisopropyl boron oxide (1.69 g, 8.99 mmol) and continued to react for 5h. TLCshowed that almost all raw material turned into product. 100 mL 1 N HCl was added into the system, and extracted withDCM(100 mL33).The combined organic phase was washed with brine (50 mL31) and then dried with anhydrous sodiumsulfate. After filtration and concentration, the residue was purified with silica gel column (petroleum ether: ethyl acetate= 3:1) to afford 700 mg product, yield 50%.1H NMR (400 MHz, CDCl3): δ 8.21(d, J = 8.6 Hz, 2H), 7.33(td, J = 8.3, 6.7 Hz, 1H), 7.13 (d, J = 8.6 Hz, 2H), 6.87(dtd,J = 7.6, 5.0, 2.5 Hz, 2H), 6.80(dt, J = 10.0, 2.3 Hz, 1H).
50% With n-butyllithium In tetrahydrofuran; diethyl ether at -70℃; for 5h; 15.4 Step 4: (4-(3-fluorophenoxy)phenyl)boric acid To a dried 25 mL three-necked-flask was added 100 mL ultra dry THF and 1-(4-bromophenoxy)-3-fluorobenzene(2.00 g, 7.49 mmol). The flask was then cooled to - 70°C in dry ice-ethanol bath. N-butyl lithium ether solution (1.6 M,9.73 mmol) was slowly added into the mixture, and the resulting solution was continued to react at the same temperature.The reacting solution was added with triisopropyl boron oxide (1.69 g, 8.99 mmol) and continued to react for 5h. TLCshowed that almost all raw material turned into product. 100 mL 1 N HCl was added into the system, and extracted withDCM(100 mL33).The combined organic phase was washed with brine (50 mL31) and then dried with anhydrous sodiumsulfate. After filtration and concentration, the residue was purified with silica gel column (petroleum ether: ethyl acetate= 3:1) to afford 700 mg product, yield 50%.1H NMR (400 MHz, CDCl3): δ 8.21(d, J = 8.6 Hz, 2H), 7.33(td, J = 8.3, 6.7 Hz, 1H), 7.13 (d, J = 8.6 Hz, 2H), 6.87(dtd,J = 7.6, 5.0, 2.5 Hz, 2H), 6.80(dt, J = 10.0, 2.3 Hz, 1H).
  • 7
  • [ 1029438-36-5 ]
  • (1R,3R)-3-{4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl}cyclohexyl acetate [ No CAS ]
  • (1R,3R)-3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With tripotassium phosphate tribasic In 1,4-dioxane; water monomer Reflux; Inert atmosphere; 15.5 Step 5: (1R, 3R)-3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl) cyclohexyl acetate To a dried 25 mL two-necked-flask was added successively (1R, 3R)-3-(4-amino-3-iodo-1h-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl acetate (0.10 g, 0.25 mmol), (4-(3-fluorophenoxy) phenyl)boric acid (0.12 g, 0.50 mmol), potassiumphosphate (0.16 g, 0.75 mmol), 10 mL of 1,4-dioxane and 5 mL of water. The mixture was exchanged 3 times withAr and then heated to reflux. The resulting solution was added rapidly with tetratriphenylphosphine palladium (0.10 g,0.05 mmol) and then reacted for 2h. LCMS showed that the reaction was completed. The reaction system was cooledand then mixed with 10 mL H2O, and extracted with DCM (8 mL33).The combined organic phase waswashed with brine(8 mL33) and dried with anhydrous sodium sulfate. After filtration and concentration, the residue was purified with silicagel column (DCM: MeOH = 100: 1-100: 2) to afford 50 mg product, yield 40%.MS ESI: m/z =462, [M+H]+.
40% With tripotassium phosphate tribasic In 1,4-dioxane; water monomer Reflux; Inert atmosphere; 15.5 Step 5: (1R, 3R)-3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl) cyclohexyl acetate To a dried 25 mL two-necked-flask was added successively (1R, 3R)-3-(4-amino-3-iodo-1h-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl acetate (0.10 g, 0.25 mmol), (4-(3-fluorophenoxy) phenyl)boric acid (0.12 g, 0.50 mmol), potassiumphosphate (0.16 g, 0.75 mmol), 10 mL of 1,4-dioxane and 5 mL of water. The mixture was exchanged 3 times withAr and then heated to reflux. The resulting solution was added rapidly with tetratriphenylphosphine palladium (0.10 g,0.05 mmol) and then reacted for 2h. LCMS showed that the reaction was completed. The reaction system was cooledand then mixed with 10 mL H2O, and extracted with DCM (8 mL33).The combined organic phase waswashed with brine(8 mL33) and dried with anhydrous sodium sulfate. After filtration and concentration, the residue was purified with silicagel column (DCM: MeOH = 100: 1-100: 2) to afford 50 mg product, yield 40%.MS ESI: m/z =462, [M+H]+.
  • 8
  • [ 1029438-36-5 ]
  • (1R,3R)-3-{4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl}cyclohexyl acetate [ No CAS ]
  • (1R,3R)-3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tripotassium phosphate tribasic / water monomer; 1,4-dioxane / Reflux; Inert atmosphere 2: lithium hydroxide monohydrate; methanol / 20 °C
  • 9
  • [ 589-87-7 ]
  • [ 1029438-36-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tripotassium phosphate tribasic; N,N-bis([1,1’-biphenyl]-2-yl)oxamide; copper (I) iodide / dimethyl sulfoxide / 10 h / 100 °C / Inert atmosphere 2: n-butyllithium / tetrahydrofuran; diethyl ether / 5 h / -70 °C
  • 10
  • [ 1029438-36-5 ]
  • 3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclopentane-1-ol [ No CAS ]
  • 3-(4-amino-3-(4-(3-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclopentane-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With tripotassium phosphate tribasic; tetrakis-(triphenylphosphine)-palladium In 1,4-dioxane; water monomer for 1h; Inert atmosphere; Reflux; 25 3-(4-amino-3-(4 - (3-fluorophenoxy) phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl) cyclopentane-1-ol To a 25 mL two-necked-flask was added successively 3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclopentane-1-ol (0.50 g, 1.45 mmol), (4-(3-fluorophenoxy)phenyl)boric acid (0.40 g, 1.74 mmol), potassium phosphate(0.92 g, 4.35 mmol), tetratriphenylphosphine palladium (72 mg, 0.22 mmol), 10 mL 1,4-dioxane and 5 mL H2O underthe protection of Ar. The mixture was heated to reflux for an hour. LCMS showed that the reaction was completed. Thereaction system was mixed with 10 mL H2O and extracted with DCM(10 mL33). The combined organic phase was driedwith anhydrous sodium sulfate. After filtration and concentration, the residue was purified with silica gel column(DCM:MeOH = 100:1) to afford 360 mg product, yield 62%.1H NMR (400 MHz, CDCl3): δ 8.39(s, 1H), 7.68(d, J = 8.7 Hz, 2H), 7.33(td, J = 8.3, 6.7 Hz, 1H), 7.21 -7.14 (m, 2H),6.87(td, J = 8.4, 2.4 Hz, 2H), 6.79(dt, J = 10.0, 2.4 Hz, 1H), 5.75(d, J = 10.2 Hz, 1H), 5.56(s, 2H), 5.47(ddd, J = 16.4,7.3, 3.1 Hz, 1H), 4.52-4.39(m, 1H), 2.58-2.35(m, 2H), 2.32-2.19(m, 2H), 2.09-2.04(m, 1H), 1.95-1.82(m, 1H).19F NMR (376 MHz, CDCl3): δ -110.43 (s).MS ESI: m/z = 406, [M+H]+.
62% With tripotassium phosphate tribasic; tetrakis-(triphenylphosphine)-palladium In 1,4-dioxane; water monomer for 1h; Inert atmosphere; Reflux; 25 3-(4-amino-3-(4 - (3-fluorophenoxy) phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl) cyclopentane-1-ol To a 25 mL two-necked-flask was added successively 3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclopentane-1-ol (0.50 g, 1.45 mmol), (4-(3-fluorophenoxy)phenyl)boric acid (0.40 g, 1.74 mmol), potassium phosphate(0.92 g, 4.35 mmol), tetratriphenylphosphine palladium (72 mg, 0.22 mmol), 10 mL 1,4-dioxane and 5 mL H2O underthe protection of Ar. The mixture was heated to reflux for an hour. LCMS showed that the reaction was completed. Thereaction system was mixed with 10 mL H2O and extracted with DCM(10 mL33). The combined organic phase was driedwith anhydrous sodium sulfate. After filtration and concentration, the residue was purified with silica gel column(DCM:MeOH = 100:1) to afford 360 mg product, yield 62%.1H NMR (400 MHz, CDCl3): δ 8.39(s, 1H), 7.68(d, J = 8.7 Hz, 2H), 7.33(td, J = 8.3, 6.7 Hz, 1H), 7.21 -7.14 (m, 2H),6.87(td, J = 8.4, 2.4 Hz, 2H), 6.79(dt, J = 10.0, 2.4 Hz, 1H), 5.75(d, J = 10.2 Hz, 1H), 5.56(s, 2H), 5.47(ddd, J = 16.4,7.3, 3.1 Hz, 1H), 4.52-4.39(m, 1H), 2.58-2.35(m, 2H), 2.32-2.19(m, 2H), 2.09-2.04(m, 1H), 1.95-1.82(m, 1H).19F NMR (376 MHz, CDCl3): δ -110.43 (s).MS ESI: m/z = 406, [M+H]+.
  • 11
  • [ 1029438-36-5 ]
  • (1S,4S)-4-(4-amino-3-(4-(4-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohex-1-ol [ No CAS ]
  • 4-(4-amino-3-[4-(4-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With Dess-Martin periodane In dichloromethane for 4h; Inert atmosphere; Cooling with ethanol-dry ice; 12.1 Step 1: 4-(4-amino-3-(4-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-ylcyclohex-1-one To a dried 50 mL two-necked-flask was added (1s,4S)-4-(4-amino-3-(4-(4-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohex-1-ol (0.60 g, 1.43 mmol) and 15 mL ultra dry DCM under Ar, cooled in cold ethanol bathand then 15 mL Dess-Martin reagent(0.72 g, 1.69 mmol) in DCM was added dropwise. The mixture was continued toreact for 4h. LCMS showed that the reaction was completed. 10 mL saturated ammonium chloride solution was addedinto the reaction system. The resulting solution was extracted with DCM(15 mL 3 3). The combined organic phase andwashed with brine(30 mL 3 1), dried with anhydrous sodium sulfate. After filtration and concentration, the residue waspurified with silica gel column (DCM: MeOH= 100:1.2-100:4) to afford 500 mg, yield 83%.MS ESI: m/z =418, [M+H]+.
83% With Dess-Martin periodane In dichloromethane for 4h; Inert atmosphere; Cooling with ethanol-dry ice; 12.1 Step 1: 4-(4-amino-3-(4-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-ylcyclohex-1-one To a dried 50 mL two-necked-flask was added (1s,4S)-4-(4-amino-3-(4-(4-fluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohex-1-ol (0.60 g, 1.43 mmol) and 15 mL ultra dry DCM under Ar, cooled in cold ethanol bathand then 15 mL Dess-Martin reagent(0.72 g, 1.69 mmol) in DCM was added dropwise. The mixture was continued toreact for 4h. LCMS showed that the reaction was completed. 10 mL saturated ammonium chloride solution was addedinto the reaction system. The resulting solution was extracted with DCM(15 mL 3 3). The combined organic phase andwashed with brine(30 mL 3 1), dried with anhydrous sodium sulfate. After filtration and concentration, the residue waspurified with silica gel column (DCM: MeOH= 100:1.2-100:4) to afford 500 mg, yield 83%.MS ESI: m/z =418, [M+H]+.
  • 12
  • [ 372-20-3 ]
  • [ 1029438-36-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tripotassium phosphate tribasic; N,N-bis([1,1’-biphenyl]-2-yl)oxamide; copper (I) iodide / dimethyl sulfoxide / 10 h / 100 °C / Inert atmosphere 2: n-butyllithium / tetrahydrofuran; diethyl ether / 5 h / -70 °C
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