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[ CAS No. 1801841-62-2 ] {[proInfo.proName]}

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Chemical Structure| 1801841-62-2
Chemical Structure| 1801841-62-2
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Quality Control of [ 1801841-62-2 ]

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Product Details of [ 1801841-62-2 ]

CAS No. :1801841-62-2 MDL No. :MFCD31672865
Formula : C5H3ClFIN2 Boiling Point : -
Linear Structure Formula :- InChI Key :MLXSRTXYRGAHOE-UHFFFAOYSA-N
M.W : 272.45 Pubchem ID :118246115
Synonyms :

Calculated chemistry of [ 1801841-62-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.33
TPSA : 38.91 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.59
Log Po/w (XLOGP3) : 1.88
Log Po/w (WLOGP) : 2.49
Log Po/w (MLOGP) : 1.78
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.16
Solubility : 0.19 mg/ml ; 0.000696 mol/l
Class : Soluble
Log S (Ali) : -2.32
Solubility : 1.31 mg/ml ; 0.0048 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.51
Solubility : 0.084 mg/ml ; 0.000308 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.32

Safety of [ 1801841-62-2 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1801841-62-2 ]

* 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 [ 1801841-62-2 ]

[ 1801841-62-2 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 1354223-71-4 ]
  • [ 1801841-62-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 2: iodine; silver sulphate / ethanol / 16 h / 50 °C
Multi-step reaction with 2 steps 1: hydrogenchloride / acetonitrile; 1,4-dioxane / 2 h / 25 °C 2: toluene-4-sulfonic acid; N-iodo-succinimide / acetonitrile / 16 h / 70 °C
Multi-step reaction with 2 steps 1: hydrogenchloride / 1,4-dioxane; acetonitrile / 2 h / 25 °C 2: N-iodo-succinimide; toluene-4-sulfonic acid / acetonitrile; water monomer / 16 h / 70 °C
Multi-step reaction with 2 steps 1: hydrogenchloride / 1,4-dioxane; acetonitrile / 2 h / 25 °C 2: toluene-4-sulfonic acid; N-iodo-succinimide / acetonitrile / 16 h / 70 °C

  • 2
  • [ 628691-93-0 ]
  • 2-chloro-3-fluoro-5-iodo-4-aminopyridine [ No CAS ]
  • 3
  • [ 1227577-03-8 ]
  • 2-chloro-3-fluoro-5-iodo-4-aminopyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iodine; silver sulfate; In ethanol; at 50℃; for 16h; 3.72.3. Step iii): 2-chloro-3-fluoro-5-iodine-4-aminopyridine To a solution of iodine (5.13 g, 20.2 mmol, 1.0 eq) in EtOH (50 mL) is added silver sulphate (6.30 g, 20.2 mmol, 1.0 eq) and <strong>[1227577-03-8]2-chloro-3-fluoro-4-aminopyridine</strong> (2.95 g, 20.2 mmol, 1.0 eq). The reaction stirred at 50C for 16 h. The reaction mixture is filtered and the solvent is evaporated. The residue is diluted in DCM, washed with aqueous Na2S203 solution, dried over Na2S04, and the solvent is removed under vacuum to afford the desired compound as a pale brown solid.
  • 4
  • [ 97-94-9 ]
  • [ 1801841-62-2 ]
  • [ 2071268-93-2 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In hexane at 55℃; for 20h; Inert atmosphere; 3.72.4.iv 3.72.4. Step iv): 2-chloro-5-ethyl-3-fluoro-4-aminopyridine 3.72.4. Step iv): 2-chloro-5-ethyl-3-fluoro-4-aminopyridine The PdCl2dppf complex with DCM (2.48 g, 3.04 mmol, 0.2 eq) and Cs2C03 (14.89 g, 45.69 mmol, 3.0 eq) are added in a round bottom flask and degassed under nitrogen. 2-Chloro-3-fluoro-5- iodine-4-aminopyridine (4.14 g, 15.23 mmol, 1.0 eq) and triethylborane (1M in hexane) (20.0 mL, 20.0 mmol, 1.3 eq) are added and the reaction is stirred at 55°C for 20h. The reaction is filtered through celite and washed the solid pad with ethyl acetate. The organic layer is washed with water. The organic layer is dried over Na2S04, filtered and removed under vacuum. The residue is purified by silica chromatography (ethyl acetate/pet. ether 40-60, from 10-50%) to afford the desired compound.
  • 5
  • [ 64-17-5 ]
  • [ CAS Unavailable ]
  • [ 1801841-62-2 ]
  • [ 2454397-74-9 ]
YieldReaction ConditionsOperation in experiment
81% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine at 90℃; for 40h; Step B: 4-Amino-6-chloro-5-fluoronicotinic acid ethyl ester Compound 2-chloro-3-fluoro-5-iodopyridin-4-amine (5.4 g, 19.82 mmol), Pd(dppf)Cl (695 mg, 0.991 mmol) and triethylamine (555 mg, 49.6 mmol) were dispersed in In absolute ethanol, heated to 90 under carbon monoxide atmosphere for 40h.After the reaction was completed, the reaction solution was filtered through celite, and the filtrate was concentrated and purified by FCC (SiO 2 , EA/DCM=0-100%) to obtain ethyl 4-amino-6-chloro-5-fluoronicotinic acid as a yellow solid. Ester (3.5 g, 81% yield).
74% With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 80℃; for 15h; Inert atmosphere; 15.2 Step 2 Under nitrogen protection stirring at 25 degrees CelsiusTo a solution of compound 78-1 (1 g, 3.67 mmol, 1.0 equiv) in ethanol (10 mL) was added triethylamine (1.38 g, 12.96 mmol,3.6 equiv) and dichlorobis(triphenylphosphine)palladium (266 mg, 0.36 mmol, 0.1 equiv).The mixture was reacted at 80 degrees Celsius for 15 hours in a carbon monoxide atmosphere (3 atmospheres), and the reaction process was monitored by liquid quality. After the reaction, the reaction solution was cooled to 25 degrees Celsius, filtered through celite, and the filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography, the mobile phase was eluted with a gradient of 0%→31% ethyl acetate/petroleum ether, and the obtained fractions were evaporated under reduced pressure to remove the solvent to obtain compound 78-2 (yellow solid, 660 mg) , yield 74%).
With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 80℃; for 15h; Inert atmosphere; E [0319] Step E: To a solution of 2-chloro-3-fluoro-5-iodo-pyridin-4-amine (78.4 g, 288 mmol, 1.0 eq) in EtOH (1500 mL) was added Pd(PPh3)2Cl2 (20.2 g, 28.8 mmol, 0.1 eq) and Et3N (105 g, 1.04 mol, 144 mL, 3.61 eq) under nitrogen. The suspension was degassed under vacuum and purged with nitrogen several times. The mixture was stirred under CO (15.0 psi) at 80 °C for 15 hours. Upon completion, the mixture was filtered and the filtrate was concentrated under vacuum to remove 70% of MeOH and the residue was filtered. The combined filter cakes were concentrated under vacuum ethyl 4-amino-6-chloro-5-fluoro- pyridine-3 -carboxylate (142 g, crude) was obtained as a yellow solid. LCMS [ESI, M+l]: 219. [0320] 'H NMR (400 MHz, dmso-d6) d = 8.36 (s, 1H), 7.49 - 7.42 (m, 2H), 4.31 (q, J= 7.2 Hz, 2H), 1.31 (t, J= 7.2 Hz, 3H).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine at 65℃; for 4h; 22.1 Step 1: A mixture of 50-1 (15 g, 55.2 mmol) , TEA (23 mL, 165.3 mmol) and Pd (dppf) Cl2(4 g, 5.52 mmol) in EtOH (150 mL) was stirred at 65 C for 4 hours under 1 atm of CO atmosphere. After being cooled to room temperature, the mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 10/1) to afford 67-1.
81 % With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine at 80℃; Step 4: 4-Amino-6-chloro-5-fluoronicotinic acid ethyl ester 4-Amino-2-chloro-3-fluoro-5-iodopyridine (30g, 110.3mmol, 1.0eq), triethylamine (33.4g, 330.9mmol, 3.0eq), [1,1'-bis(di(di)) Phenylphosphino)ferrocene]palladium dichloride (8.07g, 11.03mmol, 0.1eq) was dissolved in ethanol (750mL), replaced by carbon monoxide gas twice, and reacted at 80 degrees overnight under the protection of carbon monoxide, and the reaction solution was cooled to room temperature, Concentrated, the concentrated residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate/dichloromethane=5/1/1, volume ratio) to obtain 4-amino-6-chloro-5-fluoronicotinic acid ethyl ester (19.6 g, yield 81%), off-white solid.
68 g With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 80℃; Step 2 To a solution of 2-chloro-3-fluoro-5-iodopyridin-4-amine (90 g, 330.33 mmol, 1 equiv) in ethanol (1700 mL) was added Pd(PPh3)2Cl2 (23 g, 33.03 mmol, 0.1 equiv) and TEA (120 g, 1189.21 mmol, 3.6 equiv) and was stirred for 15 h at 80oC under CO (15 Psi) atmosphere. The resulting mixture was filtered, the filtrate was concentrated under reduced pressure to remove 70% of ethanol and the residue was filtered. The filter cake was concentrated under reduced pressure to afford 134-h (68 g, 94.16%) as a yellow solid m/z: [M+H]+Calcd for C8H9ClFN2O2219.0;Found 219.0.

  • 6
  • [ 770697-94-4 ]
  • [ 1801841-62-2 ]
  • [ 2454397-76-1 ]
YieldReaction ConditionsOperation in experiment
100% With tetrakis-(triphenylphosphine)-palladium In N,N-dimethyl-formamide at 100℃; for 3h; Molecular sieve; Inert atmosphere; 1.2 Step 2: Synthesis of 4-amino-6-chloro-5-fluoronicotinonitrile Compound 2-chloro-3-fluoro-5-iodopyridin-4-amine (7.7 g, 28.26 mmol) and Zn(CN)2 (4.32 g, 36.74 mmol) were dissolved in dry DMF (150 mL), then added Pd(PPh 3 ) 4 (1.63 g, 1.41 mmol) and 4A molecular sieve (2.5 g) were replaced with nitrogen, heated to 100° C. under nitrogen atmosphere and stirred for 3 hours. After the reaction was completed, the solid was removed by filtration, the solution was cooled to room temperature, 300 mL of water was added to dilute the reaction solution, the solid was precipitated, filtered, the solid was washed with water, and dried in vacuo to obtain a crude product that was directly used in the next step. (4.85 g, yield: 100%).
88.6% With tetrakis-(triphenylphosphine)-palladium In N,N-dimethyl-formamide at 100℃; for 3h; Molecular sieve; [0512] To a mixture of 2-chIoro-3-fluoro-5-iodopyridin-4-amine (10.0 g, 36.7 mmol, 1.0 equiv), 4A molecular sieve (3.00 g) and Zn(CN)2 (5.60 g, 47.7 mmol, 3.03 mL, 1.3 equiv) in DMF (200 mL) was added Pd(PPh3)4 (2.12 g, 1.84 mmol, 0.05 equiv). The mixture was stirred at 100 °C for 3 h prior to being diluted with H2O (30 mL) and extracted with ethyl acetate (3 c 30 L). The combined organic layer was dried over anh Na2SC>4, filtered and the filtrated was concentrated under reduced pressure to afford 4-amino-6-chloro-5-fluoronicotinonitrile (6.00 g, 32.5 mmol, 88.6 % yield) as a yellow solid. LCMS [ESI, M+l]: 172.
83% With tetrakis-(triphenylphosphine)-palladium In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere; D Step D. 4-amino-6-chloro-5-fluoro-pyridine-3-carbonitrile. To a mixture of 2-chloro-3- fluoro-5-iodopyridin-4-amine (440 g, 1.61 mol, 1.0 eq) and 4A MS (150 g) in DMF (3.5 L) was added Pd(PPh3)4 (93.31 g, 80.75 mmol, 0.05 eq) and Zn(CN)2 (246.54 g, 2.10 mol, 133.27 mL, 1.3 eq) in one portion at 25°C under N2.Then the mixture was heated to 100 °C and stirred for 2 hours. The mixture was cooled to 20 °C, then poured into brine (2000 mL) and stirred for 5 min. The aqueous phase was extracted with ethyl acetate (2000 mL × 6). The combined organic phase was washed with brine (2000 mL*3), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The crude product1100gwas triturated with ethyl acetate (100 mL) at 25oC for 30 min, filtered and concentrated in vacuum. 4-amino-6-chloro-5-fluoro-pyridine-3-carbonitrile (230 g, 83% yield) was obtained as a yellow solid.1H NMR (400 MHz, DMSO-d6) d = 8.20 (s, 1H), 7.65 (br s, 2H).
  • 7
  • [ 1801841-62-2 ]
  • [ 2454396-92-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2: sulfuric acid / 1 h / 60 °C
Multi-step reaction with 2 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: ammonia / methanol / 12 h / 35 °C
  • 8
  • [ 1801841-62-2 ]
  • [ 2454491-15-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran / 16 h / 25 °C
Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve; Inert atmosphere 2: sulfuric acid / 6 h / 120 °C
  • 9
  • [ 1801841-62-2 ]
  • [ 2454491-18-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2.1: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran / 16 h / 25 °C 3.1: trichlorophosphate / 2 h / 90 °C 3.2: 16 h / 25 °C 4.1: sodium methoxide / N,N-dimethyl-formamide / 0.17 h 4.2: 2 h / 25 °C
Multi-step reaction with 4 steps 1.1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve; Inert atmosphere 2.1: sulfuric acid / 6 h / 120 °C 3.1: trichlorophosphate / 4 h / 90 °C 3.2: 24 h / 20 °C 4.1: sodium methoxide / N,N-dimethyl-formamide / 0.17 h / 20 °C 4.2: 2 h / 20 °C
  • 10
  • [ 1801841-62-2 ]
  • [ 2454491-14-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2.1: sodium hydroxide; lithium hydroxide monohydrate / tetrahydrofuran / 16 h / 25 °C 3.1: trichlorophosphate / 2 h / 90 °C 3.2: 16 h / 25 °C 4.1: sodium methoxide / N,N-dimethyl-formamide / 0.17 h 4.2: 2 h / 25 °C 5.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 6 h / 90 °C
Multi-step reaction with 5 steps 1.1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve; Inert atmosphere 2.1: sulfuric acid / 6 h / 120 °C 3.1: trichlorophosphate / 4 h / 90 °C 3.2: 24 h / 20 °C 4.1: sodium methoxide / N,N-dimethyl-formamide / 0.17 h / 20 °C 4.2: 2 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 3 h / 90 °C
  • 11
  • [ 1801841-62-2 ]
  • [ 2454396-93-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: ammonia / methanol / 12 h / 35 °C 3: acetic acid / 4 h / 135 °C
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2: sulfuric acid / 1 h / 60 °C 3: acetic acid / 4 h / 135 °C
  • 12
  • [ 1801841-62-2 ]
  • [ 2454396-94-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2: sulfuric acid / 1 h / 60 °C 3: 3 h / 150 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 120 °C
Multi-step reaction with 4 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: ammonia / methanol / 12 h / 35 °C 3: 3 h / 150 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 120 °C
Multi-step reaction with 4 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: ammonia / methanol / 12 h / 35 °C 3: acetic acid / 4 h / 135 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 3 h / 110 °C
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2: sulfuric acid / 1 h / 60 °C 3: acetic acid / 4 h / 135 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 3 h / 110 °C

  • 13
  • [ 1801841-62-2 ]
  • [ 2454491-20-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2: sulfuric acid / 1 h / 60 °C 3: acetic anhydride / 36 h / 185 °C
Multi-step reaction with 3 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: ammonia / methanol / 12 h / 35 °C 3: acetic anhydride / 36 h / 185 °C
  • 14
  • [ 1801841-62-2 ]
  • [ 2454397-79-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2: sulfuric acid / 1 h / 60 °C 3: acetic anhydride / 36 h / 185 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 110 °C
Multi-step reaction with 4 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: ammonia / methanol / 12 h / 35 °C 3: acetic anhydride / 36 h / 185 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 110 °C
  • 15
  • [ 1801841-62-2 ]
  • [ 2454397-36-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 6 h / 0 - 110 °C / Inert atmosphere 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / Inert atmosphere 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 5 h / 80 °C / Inert atmosphere
Multi-step reaction with 8 steps 1.1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve; Inert atmosphere 2.1: sulfuric acid / 6 h / 120 °C 3.1: trichlorophosphate / 4 h / 90 °C 3.2: 24 h / 20 °C 4.1: sodium methoxide / N,N-dimethyl-formamide / 0.17 h / 20 °C 4.2: 2 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 3 h / 90 °C 6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / Cooling with ice 6.2: 16 h / 20 °C 7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / Cooling with ice 8.1: sodium tertiary butoxide / toluene / 0.5 h / Cooling with ice
  • 16
  • [ 1801841-62-2 ]
  • [ 2454396-50-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2.1: tetrahydrofuran / 0.17 h / 25 °C 3.1: ammonia / methanol / 1 h / 25 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 6 h / 0 - 110 °C / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C 6.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 80 °C 7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 6 h / 90 °C / Inert atmosphere 8.1: chloro-trimethyl-silane / acetonitrile / 0.5 h / 0 °C / Molecular sieve 8.2: 17.5 h / 0 - 15 °C / Molecular sieve
Multi-step reaction with 8 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 6 h / 0 - 110 °C / Inert atmosphere 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / Inert atmosphere 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 5 h / 80 °C / Inert atmosphere 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 5 h / 90 °C / Inert atmosphere 8: hydrogenchloride / acetonitrile; 1,4-dioxane / 1 h / 25 °C
  • 17
  • [ 1801841-62-2 ]
  • [ 2454488-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2.1: tetrahydrofuran / 0.17 h / 25 °C 3.1: ammonia / methanol / 1 h / 25 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 6 h / 0 - 110 °C / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C 6.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 80 °C 7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 6 h / 90 °C / Inert atmosphere 8.1: chloro-trimethyl-silane / acetonitrile / 0.5 h / 0 °C / Molecular sieve 8.2: 17.5 h / 0 - 15 °C / Molecular sieve 9.1: triethylamine / dichloromethane / 1 h / -40 - 10 °C
Multi-step reaction with 9 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 6 h / 0 - 110 °C / Inert atmosphere 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / Inert atmosphere 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 5 h / 80 °C / Inert atmosphere 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 5 h / 90 °C / Inert atmosphere 8: hydrogenchloride / acetonitrile; 1,4-dioxane / 1 h / 25 °C 9: triethylamine / dichloromethane / 1 h / -40 - 10 °C
  • 18
  • [ 1801841-62-2 ]
  • [ 2454396-93-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2: sulfuric acid / 1 h / 60 °C 3: 3 h / 150 °C
Multi-step reaction with 3 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: ammonia / methanol / 12 h / 35 °C 3: 3 h / 150 °C
  • 19
  • [ 1801841-62-2 ]
  • [ 2454396-95-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2.1: sulfuric acid / 1 h / 60 °C 3.1: 3 h / 150 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 120 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C
Multi-step reaction with 5 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2.1: ammonia / methanol / 12 h / 35 °C 3.1: 3 h / 150 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 120 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C
Multi-step reaction with 5 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2.1: ammonia / methanol / 12 h / 35 °C 3.1: acetic acid / 4 h / 135 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 3 h / 110 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2.1: sulfuric acid / 1 h / 60 °C 3.1: acetic acid / 4 h / 135 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 3 h / 110 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C

  • 20
  • [ 1801841-62-2 ]
  • [ 2454396-96-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2.1: sulfuric acid / 1 h / 60 °C 3.1: 3 h / 150 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 120 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C 6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 5 h / 105 °C / Inert atmosphere
Multi-step reaction with 6 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2.1: ammonia / methanol / 12 h / 35 °C 3.1: 3 h / 150 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 120 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C 6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 5 h / 105 °C / Inert atmosphere
Multi-step reaction with 6 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2.1: ammonia / methanol / 12 h / 35 °C 3.1: acetic acid / 4 h / 135 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 3 h / 110 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C 6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 5 h / 105 °C / Inert atmosphere
Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2.1: sulfuric acid / 1 h / 60 °C 3.1: acetic acid / 4 h / 135 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 3 h / 110 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C 6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 5 h / 105 °C / Inert atmosphere

  • 21
  • [ 1801841-62-2 ]
  • [ 2454396-97-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2.1: ammonia / methanol / 12 h / 35 °C 3.1: 3 h / 150 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 120 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C 6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 5 h / 105 °C / Inert atmosphere 7.1: hydrogenchloride / acetonitrile; 1,4-dioxane / 1 h / 20 °C
Multi-step reaction with 7 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2.1: ammonia / methanol / 12 h / 35 °C 3.1: acetic acid / 4 h / 135 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 3 h / 110 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C 6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 5 h / 105 °C / Inert atmosphere 7.1: hydrogenchloride / acetonitrile; 1,4-dioxane / 1 h / 20 °C
Multi-step reaction with 7 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2.1: sulfuric acid / 1 h / 60 °C 3.1: 3 h / 150 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 120 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C 6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 5 h / 105 °C / Inert atmosphere 7.1: hydrogenchloride / acetonitrile; 1,4-dioxane / 1 h / 20 °C
Multi-step reaction with 7 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2.1: sulfuric acid / 1 h / 60 °C 3.1: acetic acid / 4 h / 135 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 3 h / 110 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C 6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 5 h / 105 °C / Inert atmosphere 7.1: hydrogenchloride / acetonitrile; 1,4-dioxane / 1 h / 20 °C

  • 22
  • [ 1801841-62-2 ]
  • [ 2454488-33-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2.1: ammonia / methanol / 12 h / 35 °C 3.1: 3 h / 150 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 120 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C 6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 5 h / 105 °C / Inert atmosphere 7.1: hydrogenchloride / acetonitrile; 1,4-dioxane / 1 h / 20 °C 8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C
Multi-step reaction with 8 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2.1: ammonia / methanol / 12 h / 35 °C 3.1: acetic acid / 4 h / 135 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 3 h / 110 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C 6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 5 h / 105 °C / Inert atmosphere 7.1: hydrogenchloride / acetonitrile; 1,4-dioxane / 1 h / 20 °C 8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C
Multi-step reaction with 8 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2.1: sulfuric acid / 1 h / 60 °C 3.1: 3 h / 150 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 120 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C 6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 5 h / 105 °C / Inert atmosphere 7.1: hydrogenchloride / acetonitrile; 1,4-dioxane / 1 h / 20 °C 8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C
Multi-step reaction with 8 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 3 h / 100 °C / Molecular sieve 2.1: sulfuric acid / 1 h / 60 °C 3.1: acetic acid / 4 h / 135 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 3 h / 110 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / pH 10 5.2: 0.5 h / -40 °C 6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 5 h / 105 °C / Inert atmosphere 7.1: hydrogenchloride / acetonitrile; 1,4-dioxane / 1 h / 20 °C 8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C

  • 23
  • [ 1801841-62-2 ]
  • [ 2454488-46-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2.1: tetrahydrofuran / 0.17 h / 25 °C 3.1: ammonia / methanol / 1 h / 25 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 6 h / 0 - 110 °C / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C 6.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 80 °C 7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 6 h / 90 °C / Inert atmosphere 8.1: chloro-trimethyl-silane / acetonitrile / 0.5 h / 0 °C / Molecular sieve 8.2: 17.5 h / 0 - 15 °C / Molecular sieve 9.1: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 0.5 h / 0 °C
Multi-step reaction with 9 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 6 h / 0 - 110 °C / Inert atmosphere 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -40 °C / Inert atmosphere 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 5 h / 80 °C / Inert atmosphere 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 5 h / 90 °C / Inert atmosphere 8: hydrogenchloride / acetonitrile; 1,4-dioxane / 1 h / 25 °C 9: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 0.5 h / 0 °C
  • 24
  • [ 1801841-62-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C
Multi-step reaction with 2 steps 1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C
Multi-step reaction with 2 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C
Multi-step reaction with 2 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: tetrahydrofuran / 0.33 h / 25 °C / Inert atmosphere

  • 25
  • [ 1801841-62-2 ]
  • [ 2454397-75-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C
Multi-step reaction with 3 steps 1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C
Multi-step reaction with 3 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C
Multi-step reaction with 2 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: ammonia / methanol; tetrahydrofuran / 16 h / 0 - 20 °C

  • 26
  • [ 1801841-62-2 ]
  • [ 2454396-80-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / 775.74 Torr / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 6 h / 0 - 110 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C
Multi-step reaction with 4 steps 1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C
Multi-step reaction with 4 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 110 °C
Multi-step reaction with 4 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: tetrahydrofuran / 0.33 h / 25 °C / Inert atmosphere 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 0 - 90 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: ammonia / methanol; tetrahydrofuran / 16 h / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 100 °C

  • 27
  • [ 1801841-62-2 ]
  • [ 2621928-58-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / water; tetrahydrofuran / 2 h / 60 °C / Inert atmosphere 7.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C
Multi-step reaction with 8 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / water; tetrahydrofuran / 2 h / 60 °C / Inert atmosphere 8: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C
  • 28
  • [ 1801841-62-2 ]
  • [ 2621936-00-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 1 h / 90 °C / Inert atmosphere
Multi-step reaction with 6 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 2 h / 60 °C / Inert atmosphere
Multi-step reaction with 7 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 1 h / 90 °C / Inert atmosphere
Multi-step reaction with 7 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 2 h / 60 °C / Inert atmosphere

  • 29
  • [ 1801841-62-2 ]
  • [ 2621928-90-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 1 h / 90 °C / Inert atmosphere 7.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C
Multi-step reaction with 7 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 2 h / 60 °C / Inert atmosphere 7.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C
Multi-step reaction with 8 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 2 h / 60 °C / Inert atmosphere 8: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C
Multi-step reaction with 8 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 1 h / 90 °C / Inert atmosphere 8: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C

  • 30
  • [ 1801841-62-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere 7.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C 8.1: deuteromethanol; cesium fluoride / N,N-dimethyl acetamide / 12 h / 40 °C
Multi-step reaction with 8 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere 7.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C 8.1: deuteromethanol; cesium fluoride / N,N-dimethyl acetamide / 12 h / 40 °C
Multi-step reaction with 9 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere 8: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C 9: deuteromethanol; cesium fluoride / N,N-dimethyl acetamide / 12 h / 40 °C
Multi-step reaction with 9 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere 8: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C 9: deuteromethanol; cesium fluoride / N,N-dimethyl acetamide / 12 h / 40 °C

  • 31
  • [ 1801841-62-2 ]
  • [ 2454397-75-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C
Multi-step reaction with 3 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: tetrahydrofuran / 0.33 h / 25 °C / Inert atmosphere 3: ammonia / methanol / 1 h / 25 °C
  • 32
  • [ 1801841-62-2 ]
  • [ 2621932-53-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: sodium tertiary butoxide / toluene / 0.5 h / 0 - 10 °C 4.2: 46 h / -10 - 25 °C 5.1: N-ethyl-N,N-diisopropylamine / 2-methyltetrahydrofuran / 2 h / 0 - 25 °C / Molecular sieve 6.1: tripotassium phosphate tribasic; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate / toluene / 4 h / 65 °C / Inert atmosphere
Multi-step reaction with 7 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.17 h / 25 °C 3.1: ammonia / methanol / 1 h / 25 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5.1: sodium tertiary butoxide / toluene / 0.5 h / 0 - 10 °C 5.2: 46 h / -10 - 25 °C 6.1: N-ethyl-N,N-diisopropylamine / 2-methyltetrahydrofuran / 2 h / 0 - 25 °C / Molecular sieve 7.1: tripotassium phosphate tribasic; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate / toluene / 4 h / 65 °C / Inert atmosphere
Multi-step reaction with 7 steps 1.1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2.1: tetrahydrofuran / 0.17 h / 25 °C 3.1: ammonia / methanol / 1 h / 25 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 110 °C 5.1: sodium tertiary butoxide / toluene / 1 h / 25 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine / 2-methyltetrahydrofuran / 1 h / 25 °C / Molecular sieve 6.2: 2 h / 25 °C / Molecular sieve 7.1: tripotassium phosphate tribasic; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate / toluene / 4 h / 65 °C / Inert atmosphere
  • 33
  • [ 1801841-62-2 ]
  • [ 2621932-61-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 7 h / 60 °C / Molecular sieve; Inert atmosphere
Multi-step reaction with 5 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 110 °C 5: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 7 h / 60 °C / Molecular sieve; Inert atmosphere
  • 34
  • [ 1801841-62-2 ]
  • [ 2621932-62-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 7 h / 60 °C / Molecular sieve; Inert atmosphere 5.1: Cs2CO3 / 1,4-dioxane / 18 h / 20 - 80 °C / Inert atmosphere
Multi-step reaction with 6 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 110 °C 5: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 7 h / 60 °C / Molecular sieve; Inert atmosphere 6: Cs2CO3 / 1,4-dioxane / 18 h / 20 - 80 °C / Inert atmosphere
  • 35
  • [ 1801841-62-2 ]
  • [ 2621932-63-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 7 h / 60 °C / Molecular sieve; Inert atmosphere 5.1: Cs2CO3 / 1,4-dioxane / 18 h / 20 - 80 °C / Inert atmosphere 6.1: anhydrous sodium carbonate; tetrakis-(triphenylphosphine)-palladium / 1,4-dioxane / 7 h / 80 °C / Inert atmosphere
Multi-step reaction with 7 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 110 °C 5: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 7 h / 60 °C / Molecular sieve; Inert atmosphere 6: Cs2CO3 / 1,4-dioxane / 18 h / 20 - 80 °C / Inert atmosphere 7: tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate / 1,4-dioxane / 7 h / 80 °C / Inert atmosphere
  • 36
  • [ 1801841-62-2 ]
  • [ 2621932-64-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 7 h / 60 °C / Molecular sieve; Inert atmosphere 5.1: Cs2CO3 / 1,4-dioxane / 18 h / 20 - 80 °C / Inert atmosphere 6.1: anhydrous sodium carbonate; tetrakis-(triphenylphosphine)-palladium / 1,4-dioxane / 7 h / 80 °C / Inert atmosphere 7.1: hydrogen; palladium on activated charcoal / ethyl acetate / 15 h / 20 °C
Multi-step reaction with 8 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 110 °C 5: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 7 h / 60 °C / Molecular sieve; Inert atmosphere 6: Cs2CO3 / 1,4-dioxane / 18 h / 20 - 80 °C / Inert atmosphere 7: tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate / 1,4-dioxane / 7 h / 80 °C / Inert atmosphere 8: hydrogen / ethyl acetate / 15 h / 20 °C
Multi-step reaction with 8 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 110 °C 5: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 7 h / 60 °C / Molecular sieve; Inert atmosphere 6: Cs2CO3 / 1,4-dioxane / 18 h / 20 - 80 °C / Inert atmosphere 7: potassium carbonate; tetrakis-(triphenylphosphine)-palladium / water monomer / 29 h / 85 °C / Inert atmosphere 8: hydrogen; palladium on activated charcoal / dichloromethane; methanol / 16 h
  • 37
  • [ 1801841-62-2 ]
  • [ 2621932-23-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: sodium tertiary butoxide / toluene / 0.5 h / 0 - 10 °C 4.2: 46 h / -10 - 25 °C
Multi-step reaction with 5 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.17 h / 25 °C 3.1: ammonia / methanol / 1 h / 25 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5.1: sodium tertiary butoxide / toluene / 0.5 h / 0 - 10 °C 5.2: 46 h / -10 - 25 °C
Multi-step reaction with 5 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 110 °C 5: sodium tertiary butoxide / toluene / 1 h / 25 °C / Inert atmosphere
  • 38
  • [ 1801841-62-2 ]
  • [ 2621932-24-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: sodium tertiary butoxide / toluene / 0.5 h / 0 - 10 °C 4.2: 46 h / -10 - 25 °C 5.1: N-ethyl-N,N-diisopropylamine / 2-methyltetrahydrofuran / 2 h / 0 - 25 °C / Molecular sieve
Multi-step reaction with 6 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.17 h / 25 °C 3.1: ammonia / methanol / 1 h / 25 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5.1: sodium tertiary butoxide / toluene / 0.5 h / 0 - 10 °C 5.2: 46 h / -10 - 25 °C 6.1: N-ethyl-N,N-diisopropylamine / 2-methyltetrahydrofuran / 2 h / 0 - 25 °C / Molecular sieve
Multi-step reaction with 6 steps 1.1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2.1: tetrahydrofuran / 0.17 h / 25 °C 3.1: ammonia / methanol / 1 h / 25 °C 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 110 °C 5.1: sodium tertiary butoxide / toluene / 1 h / 25 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine / 2-methyltetrahydrofuran / 1 h / 25 °C / Molecular sieve 6.2: 2 h / 25 °C / Molecular sieve
  • 39
  • [ 1801841-62-2 ]
  • [ 2621933-91-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere
Multi-step reaction with 6 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere
Multi-step reaction with 7 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere
Multi-step reaction with 7 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere

  • 40
  • [ 1801841-62-2 ]
  • [ 2621933-92-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere 7.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C
Multi-step reaction with 7 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere 7.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C
Multi-step reaction with 8 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere 8: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C
Multi-step reaction with 8 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere 8: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C

  • 41
  • [ 1801841-62-2 ]
  • [ 2621927-50-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere 7.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C 8.1: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C
Multi-step reaction with 8 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere 7.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C 8.1: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C
Multi-step reaction with 9 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere 8: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C 9: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C
Multi-step reaction with 9 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere 8: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 0 °C 9: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C

  • 42
  • [ 1801841-62-2 ]
  • [ 2621933-93-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere 7.1: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C
Multi-step reaction with 7 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere 7.1: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C
Multi-step reaction with 8 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere 8: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C
Multi-step reaction with 8 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere 8: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C

  • 43
  • [ 1801841-62-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere 7.1: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C 8.1: tetrakis(actonitrile)copper(I) hexafluorophosphate / chloroform / 2 h / 50 °C
Multi-step reaction with 8 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere 7.1: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C 8.1: tetrakis(actonitrile)copper(I) hexafluorophosphate / chloroform / 2 h / 50 °C
Multi-step reaction with 9 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere 8: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C 9: tetrakis(actonitrile)copper(I) hexafluorophosphate / chloroform / 2 h / 50 °C
Multi-step reaction with 9 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere 8: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C 9: tetrakis(actonitrile)copper(I) hexafluorophosphate / chloroform / 2 h / 50 °C

  • 44
  • [ 1801841-62-2 ]
  • [ 2621927-51-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere 8: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C 9: tetrakis(actonitrile)copper(I) hexafluorophosphate / chloroform / 2 h / 50 °C 10: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 10 °C
Multi-step reaction with 10 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: tetrahydrofuran / 0.17 h / 25 °C 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 3 h / 0 - 110 °C 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 6: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 7: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere 8: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C 9: tetrakis(actonitrile)copper(I) hexafluorophosphate / chloroform / 2 h / 50 °C 10: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 10 °C
Multi-step reaction with 9 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 8 h / 90 °C / Inert atmosphere 7.1: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C 8.1: tetrakis(actonitrile)copper(I) hexafluorophosphate / chloroform / 2 h / 50 °C 9.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 10 °C
Multi-step reaction with 9 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2.1: tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 16 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / toluene / 5 h / 0 - 110 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 6 h / 80 °C 6.1: [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; potassium phosphate / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere 7.1: cesium fluoride / N,N-dimethyl-formamide / 3 h / 15 °C 8.1: tetrakis(actonitrile)copper(I) hexafluorophosphate / chloroform / 2 h / 50 °C 9.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 0.5 h / 10 °C

  • 45
  • [ 64-17-5 ]
  • [ 124-38-9 ]
  • [ 1801841-62-2 ]
  • [ 2454397-74-9 ]
YieldReaction ConditionsOperation in experiment
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine at 80℃; for 15h; D Step D. 4-amino-6-chloro-5-fluoro- pyridine-3-carboxylate. To a solution of 2-chloro-3- fluoro-5-iodo-pyridin-4-amine (78.4 g, 288 mmol, 1.0 eq) in EtOH (1500 mL) was added Pd(PPh3)2Cl2 (20.2 g, 28.8 mmol, 0.1 eq) and Et3N (105 g, 1.04 mol, 144 mL, 3.61 eq) under nitrogen. The suspension was degassed under vacuum and purged with nitrogen several times. The mixture was stirred under CO2 (15.0 psi) at 80 °C for 15 hours. Upon completion, the mixture was filtered, and the filtrate was concentrated under vacuum to remove 70% of MeOH and the residue was filtered. The combined filter cakes were concentrated under vacuum. ethyl 4-amino- 6-chloro-5-fluoro- pyridine-3-carboxylate (142 g, crude) was obtained as a yellow solid. LCMS [ESI, M+1]: 219.1H NMR (400 MHz, dmso-d6) d = 8.36 (s, 1H), 7.49 - 7.42 (m, 2H), 4.31 (q, J = 7.2 Hz, 2H), 1.31 (t, J = 7.2 Hz, 3H).
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine at 80℃; for 15h; Inert atmosphere; Step D. ethyl 4-amino-6-chloro-5-fluoro- pyridine-3 -carboxylate. To a solution of 2- chloro-3-fhioro-5-iodo-pyridin-4-amine (78.4 g, 288 mmol, 1.0 eq) in EtOH (1500 mL) was added Pd(PPh3)2Ch (20.2 g, 28.8 mmol, 0.1 eq) and EtsN (105 g, 1.04 mol, 144 mL, 3.61 eq) under nitrogen. The suspension was degassed under vacuum and purged with nitrogen several times. The mixture was stirred under CO2 (15.0 psi) at 80 °C for 15 hours. Upon completion, the mixture was filtered, and the filtrate was concentrated under vacuum to remove 70% of MeOH and the residue was filtered. The combined filter cakes were concentrated under vacuum, ethyl 4- amino-6-chl oro-5 -fluoro- pyridine-3 -carboxylate (142 g, crude) was obtained as a yellow solid. LCMS [ESI, M+l]: 219. ’H NMR (400 MHz, dmso-d6) 6 = 8.36 (s, 1H), 7.49 - 7.42 (m, 2H), 4.31 (q, J = 7.2 Hz, 2H), 1.31 (t, J = 7.2 Hz, 3H).
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine at 80℃; for 15h; Inert atmosphere; Step D. ethyl 4-amino-6-chloro-5-fluoro- pyridine-3 -carboxylate. To a solution of 2- chloro-3-fhioro-5-iodo-pyridin-4-amine (78.4 g, 288 mmol, 1.0 eq) in EtOH (1500 mL) was added Pd(PPh3)2Ch (20.2 g, 28.8 mmol, 0.1 eq) and EtsN (105 g, 1.04 mol, 144 mL, 3.61 eq) under nitrogen. The suspension was degassed under vacuum and purged with nitrogen several times. The mixture was stirred under CO2 (15.0 psi) at 80 °C for 15 hours. Upon completion, the mixture was filtered, and the filtrate was concentrated under vacuum to remove 70% of MeOH and the residue was filtered. The combined filter cakes were concentrated under vacuum, ethyl 4- amino-6-chl oro-5 -fluoro- pyridine-3 -carboxylate (142 g, crude) was obtained as a yellow solid. LCMS [ESI, M+l]: 219. ’H NMR (400 MHz, dmso-d6) 6 = 8.36 (s, 1H), 7.49 - 7.42 (m, 2H), 4.31 (q, J = 7.2 Hz, 2H), 1.31 (t, J = 7.2 Hz, 3H).
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine at 80℃; for 15h; Inert atmosphere; Preparation of 4-amino-6-chloro-5-fluoronicotinic acid ethyl ester Under nitrogen atmosphere, to a solution of 2-chloro-3-fluoro-5-iodopyridin-4-amine (8.2 g, 30 mmol, 1.0 eq) in EtOH (150 mL) was added Pd(PPh3)2Cl2(2.1 g, 3 mmol ), 0.1eq) and TEA (11.1g, 0.11mmol, 3.6eq), the resulting reaction solution was reacted at 80° C. for 15 hours under a CO2atmosphere, and then filtered.The filtrate was concentrated under reduced pressure to 70-80% of the original volume and filtered again.The filter cakes were collected and combined and dried in vacuo to obtain the target product (quantitative yield).It was directly used in the next reaction without purification.

  • 46
  • [ 1801841-62-2 ]
  • [ 2677884-98-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: anhydrous sodium carbonate; tetrakis-(triphenylphosphine)-palladium / lithium hydroxide monohydrate; 1,2-dichloro-ethane / 3 h / 100 °C / Inert atmosphere 2: sodium thiomethoxide / ethanol; lithium hydroxide monohydrate / 4 h / 60 °C
Multi-step reaction with 2 steps 1: triethylamine; palladium diacetate; triphenylphosphine / 1,4-dioxane / 3 h / 90 °C / Inert atmosphere 2: potassium etoxide; ethanol / 2 h / 80 °C / Inert atmosphere
  • 47
  • [ 1009307-13-4 ]
  • [ 1801841-62-2 ]
  • [ 2677884-97-6 ]
YieldReaction ConditionsOperation in experiment
92.8% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; 1,2-dichloro-ethane at 100℃; for 3h; Inert atmosphere; 1.2 Step 2: Ethyl (E)-3-(4-amino-6-chloro-5-fluoropyridin-3-yl)acrylate To a stirred solution of 2-chloro-3-fluoro-5-iodopyridin-4-amine (6.00 g, 22.022 mmol, 1.00 equiv) and ethyl (2E)-3-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)prop-2-enoate (6.47 g, 28.629 mmol, 1.3 equiv) in DME (90 ml_) and H2O (30 ml_) were added Pd(PPh3)4(2.54 g, 2.202 mmol, 0.1 equiv) and Na2CC>3 (4.67 g, 44.045 mmol, 2 equiv). The resulting mixture was stirred at 100 °C for 3 h under nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluting with PE/EtOAc (5:1) to give the title compound (5.0 g,92.80%) as a light yellow oil.LCMS (ESI) m/z: [M+H]+= 245.
  • 48
  • [ 1801841-62-2 ]
  • [ 2621932-88-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 4 h / 65 °C / 760.05 Torr 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 16 h / 100 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 15 h / 80 °C / 775.74 Torr 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; potassium phosphate trihydrate / toluene / 8 h / 100 °C / Inert atmosphere
  • 49
  • [ 1801841-62-2 ]
  • [ 140-88-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; triethylamine; triphenylphosphine In 1,4-dioxane at 90℃; for 3h; Inert atmosphere; 20.2 Step 2: A mixture of 50-1 (1.0 g, 3.68 mmol) , ethyl acrylate (464 mg, 5.51 mmol) , Pd (OAc)2(66 mg, 0.29 mmol) , PPh3(116 mg, 0.44 mmol) and TEA (740 mg, 7.33 mmol) in 1, 4-dioxane (30 mL) was stirred at 90 C for 3 hours under nitrogen atmosphere. The resulting mixture was cooled, diluted with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by column on silica gel (petroleum ether/ethyl acetate = 10/7) to afford 50-2.
  • 50
  • [ 1801841-62-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: tetrahydrofuran / 0.33 h / 25 °C / Inert atmosphere 3: ammonia / methanol / 1 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 0 - 90 °C / Inert atmosphere 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 25 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / 15 h / 80 °C / Inert atmosphere 2: ammonia / methanol; tetrahydrofuran / 16 h / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 1 h / 100 °C 4: N-ethyl-N,N-diisopropylamine / dichloromethane / -40 - 20 °C
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