Alternatived Products of [ 223788-08-7 ]
Product Details of [ 223788-08-7 ]
CAS No. : 223788-08-7
MDL No. : MFCD18803546
Formula :
C8 H9 NO3
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 ]
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 ]
1
[ 67-56-1 ]
[ 66909-37-3 ]
[ 223788-08-7 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
81%
With triethylamine In dichloromethane at -78 - 25℃; for 96h;
3
[ 223788-08-7 ]
[ 66416-48-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 81 percent / Et3 N / CH2 Cl2 / 96 h / -78 - 25 °C
2: 71 percent / Pd(PPh3 )4, Bu4 NBr, K2 CO3 / toluene; H2 O / 24 h / Heating
4
[ 922-67-8 ]
[ 14205-39-1 ]
[ 223788-08-7 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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