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[ CAS No. 223788-08-7 ] {[proInfo.proName]}

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Chemical Structure| 223788-08-7
Chemical Structure| 223788-08-7
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Product Details of [ 223788-08-7 ]

CAS No. :223788-08-7 MDL No. :MFCD18803546
Formula : C8H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :NYZKFYQERYBEAB-UHFFFAOYSA-N
M.W :167.16 Pubchem ID :11788501
Synonyms :

Calculated chemistry of [ 223788-08-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.31
TPSA : 59.16 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 0.15
Log Po/w (WLOGP) : 0.47
Log Po/w (MLOGP) : 0.54
Log Po/w (SILICOS-IT) : 1.79
Consensus Log Po/w : 0.94

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.21
Solubility : 10.3 mg/ml ; 0.0618 mol/l
Class : Very soluble
Log S (Ali) : -0.95
Solubility : 18.8 mg/ml ; 0.112 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.39
Solubility : 0.684 mg/ml ; 0.00409 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 223788-08-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 223788-08-7 ]

* 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 [ 223788-08-7 ]

[ 223788-08-7 ] Synthesis Path-Downstream   1~45

  • 1
  • [ 67-56-1 ]
  • [ 66909-37-3 ]
  • [ 223788-08-7 ]
YieldReaction ConditionsOperation in experiment
39% With acetyl chloride at 0 - 25℃; for 24h;
  • 2
  • [ 358-23-6 ]
  • [ 223788-08-7 ]
  • 2-Methyl-6-trifluoromethanesulfonyloxy-nicotinic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With triethylamine In dichloromethane at -78 - 25℃; for 96h;
  • 3
  • [ 223788-08-7 ]
  • [ 66416-48-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / Et3N / CH2Cl2 / 96 h / -78 - 25 °C 2: 71 percent / Pd(PPh3)4, Bu4NBr, K2CO3 / toluene; H2O / 24 h / Heating
  • 4
  • [ 922-67-8 ]
  • [ 14205-39-1 ]
  • [ 223788-08-7 ]
YieldReaction ConditionsOperation in experiment
75.7% Stage #1: propynoic acid methyl ester; methyl 3-aminocrotonate In dimethyl sulfoxide at 100℃; for 8h; Stage #2: With sodium hydroxide In dimethyl sulfoxide at 100℃; for 4h; 2 Step 2: Preparation of methyl 2-methyl-6-hydroxynicotinate In a 1000mL reaction flask,Add methyl 3-aminocrotonate (127.5g, 1.11mol),Methyl propionate (97.8g, 1.17mol),300mL of dimethyl sulfoxide,The reaction was heated to 100 ° C for 8 hours.Sodium hydroxide (44.3 g, 1.11 mol) was added to the reaction solution, and the reaction was continued at 100 ° C for 4 hours.Cool down,Slowly pour the reaction solution into 1000mL of 1N hydrochloric acid.Precipitation of a large amount of yellow solid,Adjust to neutral with sodium carbonate,Stir for 1 hour,Suction filtration,The obtained solid was dried under vacuum and constant weight,140 g of methyl 6-hydroxy-2-methylnicotinate was obtained, 75.7%.
In methanol at 70℃; 129.a Example 129Methyl 6-{4-[(benzylsulfonyl)carbamoyl]piperidin-l-yl}-5-chIoro-2-[(2-oxopiperidin- l-yl)methyl]nicotinate 0(a) Methyl 6-hydroxy-2-methylnicotinateMethyl 3-aminocrotonate (12.6 g, 110 mmol) and methyl propiolate (9.8 g, 100 mmol) were added to MeOH (100 niL), the reaction mixture was stirred at 70 0C over night. s Added seed material and cooled to 5 0C, the precipitation was filtered and washed withIPA to give methyl 6-hydroxy-2-methylnicotinate as a colorless solid.1HNMR (400 MHz, DMSO-J6) δ 2.52 (3H, s), 3.74 (3H, s), 6.20 (IH, d), 7.81 (IH, d),12.05 (IH, bs).MSm/z: 182 (M-I) o
  • 5
  • [ 223788-08-7 ]
  • 2-((2-(3-chlorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 3 h / 80 °C 6: potassium carbonate / dimethyl sulfoxide / 2 h / 110 °C
  • 6
  • [ 223788-08-7 ]
  • 2-((2-(3-chlorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C 5: N-Bromosuccinimide / acetonitrile / 2.5 h / 80 °C 6: potassium carbonate / dimethyl sulfoxide / 2 h / 110 °C
  • 7
  • [ 223788-08-7 ]
  • 2-((2-(4-chlorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 3 h / 80 °C 6: potassium carbonate / dimethyl sulfoxide / 3 h / 110 °C
  • 8
  • [ 223788-08-7 ]
  • 2-((2-(4-chlorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridin-6-yl)formylamino)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C 5: N-Bromosuccinimide / acetonitrile / 2 h / 80 °C 6: potassium carbonate / dimethyl sulfoxide / 3 h / 110 °C
  • 9
  • [ 223788-08-7 ]
  • 2-((2-(4-fluorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 3 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 3 h / 80 °C 6: potassium carbonate / dimethyl sulfoxide / 3 h / 110 °C
  • 10
  • [ 223788-08-7 ]
  • 2-((2-(4-fluorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 3 h / 110 °C 5: N-Bromosuccinimide / acetonitrile / 2 h / 80 °C 6: potassium carbonate / dimethyl sulfoxide / 3 h / 110 °C
  • 11
  • [ 223788-08-7 ]
  • 2-((2-(4-hydroxyphenoxy)-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 4 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 4 h / 80 °C 6: boron tribromide / dichloromethane / 2.33 h / -5 - 20 °C / Inert atmosphere 7: potassium carbonate / dimethyl sulfoxide / 4 h / 110 °C
  • 12
  • [ 223788-08-7 ]
  • 2-((2-ethoxy-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: sodium ethanolate / 6 h / 90 °C 5: N-chloro-succinimide / acetonitrile / 4 h / 80 °C 6: potassium carbonate / dimethyl sulfoxide / 3 h / 110 °C
  • 13
  • [ 223788-08-7 ]
  • (2-((2-phenoxy-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formylamino)acetoxy)methyl pivalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 4 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 4 h / 80 °C 6: potassium carbonate / dimethyl sulfoxide / 1.5 h / 120 °C 7: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 50 °C
  • 14
  • [ 223788-08-7 ]
  • [ 851759-19-8 ]
YieldReaction ConditionsOperation in experiment
98.7% With trichlorophosphate; at 100℃; for 4h; Add 500mL reaction flasks one by one6-hydroxy-2-methylnicotinic acid methyl ester (140g, 0.84mol),300 mL of phosphorus oxychloride,The reaction was heated to 100 C for 4 hours.Concentrated under reduced pressure,The residue was slowly poured into 1000 mL of ice water,A large amount of gray-black solid precipitated,Stir for 1 hour,Suction filtration,The cake was air-dried at room temperature.153 g of methyl 6-chloro-2-methylnicotinate was obtained, 98.7%.
  • 15
  • [ 223788-08-7 ]
  • 2-((2-phenoxy-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 4 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 4 h / 80 °C 6: potassium carbonate / dimethyl sulfoxide / 1.5 h / 120 °C
  • 16
  • [ 223788-08-7 ]
  • 2-bromomethyl-6-chloro-nicotinic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C
Multi-step reaction with 2 steps 1: trichlorophosphate / N,N-dimethyl-formamide / 2 h / 120 °C / Inert atmosphere 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 4 h / Reflux
  • 17
  • [ 223788-08-7 ]
  • ethyl 2-chloro-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C
  • 18
  • [ 223788-08-7 ]
  • ethyl 2-phenoxy-5-hydroxy-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 4 h / 110 °C
  • 19
  • [ 223788-08-7 ]
  • 2-((2-(4-methoxyphenoxy)-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 4 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 4 h / 80 °C 6: potassium carbonate / dimethyl sulfoxide / 1.5 h / 120 °C
  • 20
  • [ 223788-08-7 ]
  • ethyl 2-phenoxy-5-hydroxy-8-chloro-1,7-naphthyridine-6carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 4 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 4 h / 80 °C
  • 21
  • [ 223788-08-7 ]
  • ethyl 2-(4-methoxyphenoxy)-5-hydroxy-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 4 h / 110 °C
  • 22
  • [ 223788-08-7 ]
  • ethyl 2-(4-methoxyphenoxy)-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 4 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 4 h / 80 °C
  • 23
  • [ 223788-08-7 ]
  • ethyl 2-phenoxy-5-hydroxy-8-bromo-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 4 h / 110 °C 5: N-Bromosuccinimide / acetonitrile / 4 h / 80 °C
  • 24
  • [ 223788-08-7 ]
  • ethyl 2,8-dichloro-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: N-chloro-succinimide / acetonitrile / 2 h / 80 °C
  • 25
  • [ 223788-08-7 ]
  • ethyl 2-(2-chlorophenoxy)-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C
  • 26
  • [ 223788-08-7 ]
  • ethyl 2-(2-chlorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C 5: N-Bromosuccinimide / acetonitrile / 2 h / 80 °C
  • 27
  • [ 223788-08-7 ]
  • ethyl 2-(2-chlorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 2 h / 80 °C
  • 28
  • [ 223788-08-7 ]
  • 2-((2-phenoxy-5-hydroxy-8-bromo-1,7-naphthyridin-6-yl)formylamino)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 4 h / 110 °C 5: N-Bromosuccinimide / acetonitrile / 4 h / 80 °C 6: potassium carbonate / dimethyl sulfoxide / 1.5 h / 120 °C
  • 29
  • [ 223788-08-7 ]
  • ethyl 2-(4-chlorophenoxy)-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C
  • 30
  • [ 223788-08-7 ]
  • ethyl 2-(3-chlorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 3 h / 80 °C
  • 31
  • [ 223788-08-7 ]
  • ethyl 2-(3-chlorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C 5: N-Bromosuccinimide / acetonitrile / 2.5 h / 80 °C
  • 32
  • [ 223788-08-7 ]
  • ethyl 2-(3-chlorophenoxy)-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C
  • 33
  • [ 223788-08-7 ]
  • ethyl 2-(4-chlorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C 5: N-Bromosuccinimide / acetonitrile / 2 h / 80 °C
  • 34
  • [ 223788-08-7 ]
  • ethyl 2-(4-fluorophenoxy)-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 3 h / 110 °C
  • 35
  • [ 223788-08-7 ]
  • ethyl 2-(4-fluorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 3 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 3 h / 80 °C
  • 36
  • [ 223788-08-7 ]
  • 2-((2,8-dichloro-5-hydroxy-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: N-chloro-succinimide / acetonitrile / 2 h / 80 °C 5: potassium carbonate / dimethyl sulfoxide / 1.5 h / 120 °C
  • 37
  • [ 223788-08-7 ]
  • ethyl 2-(4-fluorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 3 h / 110 °C 5: N-Bromosuccinimide / acetonitrile / 2 h / 80 °C
  • 38
  • [ 223788-08-7 ]
  • ethyl 2-(4-hydroxyphenoxy)-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 4 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 4 h / 80 °C 6: boron tribromide / dichloromethane / 2.33 h / -5 - 20 °C / Inert atmosphere
  • 39
  • [ 223788-08-7 ]
  • ethyl 2-ethoxy-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: sodium ethanolate / 6 h / 90 °C
  • 40
  • [ 223788-08-7 ]
  • ethyl 2-ethoxy-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: sodium ethanolate / 6 h / 90 °C 5: N-chloro-succinimide / acetonitrile / 4 h / 80 °C
  • 41
  • [ 223788-08-7 ]
  • 2-((2-(2-chlorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C 5: N-Bromosuccinimide / acetonitrile / 2 h / 80 °C 6: potassium carbonate / dimethyl sulfoxide / 2 h / 110 °C
  • 42
  • [ 223788-08-7 ]
  • ethyl 2-(4-chlorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C 5: N-chloro-succinimide / acetonitrile / 3 h / 80 °C
  • 43
  • [ 223788-08-7 ]
  • 2-((2-(2-chlorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: trichlorophosphate / 4 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 8 h / 80 °C 3: sodium ethanolate / ethanol / 24 h / 20 °C 4: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C 5: N-Bromosuccinimide / acetonitrile / 2 h / 80 °C 6: potassium carbonate / dimethyl sulfoxide / 2 h / 110 °C
  • 44
  • [ 223788-08-7 ]
  • (S)-2-chloro-6-(1-cyclopropylethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trichlorophosphate / N,N-dimethyl-formamide / 2 h / 120 °C / Inert atmosphere 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 4 h / Reflux 3: potassium carbonate; boric acid / acetonitrile / 20 °C
  • 45
  • [ 223788-08-7 ]
  • (S)-N-(5-(6-(1-cyclopropylethyl)-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-2-yl)-4-methylthiazol-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: trichlorophosphate / N,N-dimethyl-formamide / 2 h / 120 °C / Inert atmosphere 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 4 h / Reflux 3: potassium carbonate; boric acid / acetonitrile / 20 °C 4: palladium diacetate; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate / N,N-dimethyl-formamide / 100 °C
Same Skeleton Products
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