[ CAS No. 6433-72-3 ] {[proInfo.proName]}

Name: 6433-72-3|Ethyl 2-amino-1H-indole-3-carboxylate|97%
Brand: Ambeed
SKU: A190527
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Quality Control of [ 6433-72-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6433-72-3 ]

SDS Specification

Alternatived Products of [ 6433-72-3 ]

Product Details of [ 6433-72-3 ]

CAS No. :	6433-72-3	MDL No. :	MFCD01568663
Formula :	C₁₁H₁₂N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KXEKODJGRSIGAU-UHFFFAOYSA-N
M.W :	204.23	Pubchem ID :	1476606
Synonyms :

Calculated chemistry of [ 6433-72-3 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.18
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	58.79
TPSA :	68.11 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.79
Log Po/w (XLOGP3) :	2.47
Log Po/w (WLOGP) :	1.93
Log Po/w (MLOGP) :	1.5
Log Po/w (SILICOS-IT) :	1.98
Consensus Log Po/w :	1.93

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.91
Solubility :	0.252 mg/ml ; 0.00124 mol/l
Class :	Soluble
Log S (Ali) :	-3.54
Solubility :	0.0583 mg/ml ; 0.000285 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.41
Solubility :	0.0793 mg/ml ; 0.000388 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.84

Safety of [ 6433-72-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6433-72-3 ]

* 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.

Upstream synthesis route of [ 6433-72-3 ]
Downstream synthetic route of [ 6433-72-3 ]

[ 6433-72-3 ] Synthesis Path-Upstream 1~10

1
[ 65548-02-9 ]
[ 6433-72-3 ]

Yield	Reaction Conditions	Operation in experiment
44%	at 65℃; for 24 h;	Step 2. Synthesis of ethyl-2-amino-lH-indol-3-carboxyate [formula 12-3]Ethyl-2-cyano-2-(2-nitrophyenyl)acetate [formula 12-2] (16 g, 68.315 mmol) was dissolved in AcOH (200mL), Zn (17.86 g, 273.25 mmol) was added and stirred at 65°C for one day. Then Zn was deleted with celite filtering, and AcOH was removed under the reduced pressure to obtain solid product. The obtained solid was dissolved in excess dichloromethane, and then hexane was added to yield the title compound (6 g, 44percent).
44%	at 65℃; for 24 h;	Ethyl-2-cyano-2-(2-nitrophyenyl)acetate [formula 12-2] (16 g, 68.315 mmol) was dissolved in AcOH (200 mL), Zn (17.86 g, 273.25 mmol) was added and stirred at 65° C. for one day. Then Zn was deleted with celite filtering, and AcOH was removed under the reduced pressure to obtain solid product. The obtained solid was dissolved in excess dichloromethane, and then hexane was added to yield the title compound (6 g, 44percent).
33.1 g	at 55℃; for 2.5 h;	3.3. Ethyl 2-amino-5-chloro-1H-indole-3-carboxylate (7) : Compound 7 was prepared according to modified literature conditions.Crude 5 (60 g, 221 mmol) was dissolved in glacial acetic acid (600 ml) and zinc dust (40 g) was added after parts during 45 min. The mixture was stirred for 2 h without external heating (reaction is exothermic, temperature in the flask reached 55°C during reaction) and filtered through a pad of cellite. The pad was washed with acetic acid (400 ml) and solution was evaporated. The residue was then washed well with water and dried under reduced pressure. Compound 7 (46.1 g, 88percent) was obtained as brown powder and further purified by column chromatography (hexane/chloroform,0–60percent chloroform); mp: 190–193°C. 1H NMR is in agreement with literature.Crude material was used directly for the next step. 3.4. Ethyl 2-amino-1H-indole-3-carboxylate (8) : Compound 8 was prepared as described for 7 from crude 6 (44.2 g), product 8 (33.1 g, 86percent) was obtained as brown powder. 1H NMR is in agreement with literature. Crude material was used directly for the next step.

Reference： [1] Chinese Journal of Chemistry, 2013, vol. 31, # 2, p. 263 - 266
[2] Patent: WO2013/62344, 2013, A1, . Location in patent: Page/Page column 28; 99
[3] Patent: US2014/315889, 2014, A1, . Location in patent: Paragraph 0472-0474
[4] Tetrahedron Letters, 2006, vol. 47, # 2, p. 159 - 162
[5] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 20, p. 6123 - 6133,11

2
[ 65547-91-3 ]
[ 6433-72-3 ]

Reference： [1] Chinese Journal of Chemistry, 2013, vol. 31, # 2, p. 263 - 266
[2] Tetrahedron Letters, 2006, vol. 47, # 2, p. 159 - 162

3
[ 143321-89-5 ]
[ 105-56-6 ]
[ 6433-72-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 6, p. 1035 - 1038

4
[ 2727-71-1 ]
[ 105-56-6 ]
[ 6433-72-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 6, p. 1035 - 1038

5
[ 10113-39-0 ]
[ 105-56-6 ]
[ 6433-72-3 ]

Reference： [1] Synthesis, 2011, # 5, p. 764 - 768

6
[ 105-56-6 ]
[ 6433-72-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 20, p. 6123 - 6133,11
[2] Patent: US2014/315889, 2014, A1,
[3] Patent: WO2013/62344, 2013, A1,

7
[ 88-73-3 ]
[ 6433-72-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 20, p. 6123 - 6133,11

8
[ 1493-27-2 ]
[ 6433-72-3 ]

Reference： [1] Patent: US2014/315889, 2014, A1,
[2] Patent: WO2013/62344, 2013, A1,

9
[ 615-43-0 ]
[ 6433-72-3 ]

Reference： [1] Synthesis, 2011, # 5, p. 764 - 768

10
[ 6433-72-3 ]
[ 5719-08-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 20, p. 6123 - 6133,11

[ 6433-72-3 ] Synthesis Path-Downstream 1~72

1
[ 6433-72-3 ]
[ 57397-70-3 ]
[ 77740-10-4 ]

Reference： [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 2972 - 2979
[2]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 2972 - 2979

2
[ 6433-72-3 ]
[ 94-05-3 ]
[ 85516-66-1 ]

Reference： [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1425 - 1431

3
[ 6433-72-3 ]
[ 52942-64-0 ]
[ 77740-11-5 ]

Reference： [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 2972 - 2979
[2]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 2972 - 2979

4
[ 6433-72-3 ]
[ 105-36-2 ]
[ 175288-78-5 ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 745 - 754

5
[ 6433-72-3 ]
[ 762-42-5 ]
4-Oxo-1,4-dihydro-pyrimido[1,2-a]indole-2,10-dicarboxylic acid 10-ethyl ester 2-methyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 4931 - 4932

6
[ 420-04-2 ]
[ 6433-72-3 ]
2-[(aminoiminomethyl)amino]-1H-indole-3-carboxylic acid ethyl ester hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5464 - 5474

7
[ 6433-72-3 ]
[ 75-05-8 ]
2-[(1-iminoethyl)amino]-1H-indole-3-carboxylic acid ethyl ester hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5464 - 5474

10
[ 6433-72-3 ]
[ 386736-73-8 ]

Reference： [1]Helvetica Chimica Acta,2001,vol. 84,p. 2212 - 2219

11
[ 6433-72-3 ]
[ 64-19-7 ]
3-ethoxycarbonyl-1H-indole-2-diazonium; acetate [ No CAS ]

Reference： [1]Il Farmaco,2002,vol. 57,p. 97 - 100

12
[ 6433-72-3 ]
[ 77-78-1 ]
[ 55643-99-7 ]

Reference： [1]Heterocycles,2003,vol. 60,p. 2669 - 2675

13
[ 6433-72-3 ]
[ 74-88-4 ]
[ 55643-99-7 ]
1-methyl-2-methylamino-1H-indole-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Heterocycles,2003,vol. 60,p. 2669 - 2675

14
[ 65547-91-3 ]
[ 6433-72-3 ]

Reference： [1]Chinese Journal of Chemistry,2013,vol. 31,p. 263 - 266
[2]Tetrahedron Letters,2006,vol. 47,p. 159 - 162

15
[ 65548-02-9 ]
[ 6433-72-3 ]

Yield	Reaction Conditions	Operation in experiment
44%	With acetic acid; zinc; at 65℃; for 24h;	Step 2. Synthesis of ethyl-2-amino-lH-indol-3-carboxyate [formula 12-3]Ethyl-2-cyano-2-(2-nitrophyenyl)acetate [formula 12-2] (16 g, 68.315 mmol) was dissolved in AcOH (200mL), Zn (17.86 g, 273.25 mmol) was added and stirred at 65C for one day. Then Zn was deleted with celite filtering, and AcOH was removed under the reduced pressure to obtain solid product. The obtained solid was dissolved in excess dichloromethane, and then hexane was added to yield the title compound (6 g, 44%).
44%	With acetic acid; zinc; at 65℃; for 24h;	Ethyl-2-cyano-2-(2-nitrophyenyl)acetate [formula 12-2] (16 g, 68.315 mmol) was dissolved in AcOH (200 mL), Zn (17.86 g, 273.25 mmol) was added and stirred at 65 C. for one day. Then Zn was deleted with celite filtering, and AcOH was removed under the reduced pressure to obtain solid product. The obtained solid was dissolved in excess dichloromethane, and then hexane was added to yield the title compound (6 g, 44%).
33.1 g	With acetic acid; zinc; at 55℃; for 2.5h;	3.3. Ethyl 2-amino-5-chloro-1H-indole-3-carboxylate (7) : Compound 7 was prepared according to modified literature conditions.Crude 5 (60 g, 221 mmol) was dissolved in glacial acetic acid (600 ml) and zinc dust (40 g) was added after parts during 45 min. The mixture was stirred for 2 h without external heating (reaction is exothermic, temperature in the flask reached 55C during reaction) and filtered through a pad of cellite. The pad was washed with acetic acid (400 ml) and solution was evaporated. The residue was then washed well with water and dried under reduced pressure. Compound 7 (46.1 g, 88%) was obtained as brown powder and further purified by column chromatography (hexane/chloroform,0-60% chloroform); mp: 190-193C. 1H NMR is in agreement with literature.Crude material was used directly for the next step. 3.4. Ethyl 2-amino-1H-indole-3-carboxylate (8) : Compound 8 was prepared as described for 7 from crude 6 (44.2 g), product 8 (33.1 g, 86%) was obtained as brown powder. 1H NMR is in agreement with literature. Crude material was used directly for the next step.

Reference： [1]Chinese Journal of Chemistry,2013,vol. 31,p. 263 - 266
[2]Patent: WO2013/62344,2013,A1 .Location in patent: Page/Page column 28; 99
[3]Patent: US2014/315889,2014,A1 .Location in patent: Paragraph 0472-0474
[4]Tetrahedron Letters,2006,vol. 47,p. 159 - 162
[5]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6123 - 6133,11

16
[ 6433-72-3 ]
[ 654674-81-4 ]

Reference： [1]Heterocycles,2003,vol. 60,p. 2669 - 2675

17
[ 6433-72-3 ]
10-methyl-5-oxo-5,10-dihydro-4H-indolo[3,2-e][1,2,3]triazolo[1,5-a]pyrimidine-3-carbonitrile [ No CAS ]

Reference： [1]Heterocycles,2003,vol. 60,p. 2669 - 2675

18
[ 6433-72-3 ]
methyl 10-methyl-5-oxo-5,10-dihydro-4H-indolo[3,2-e][1,2,3]triazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Reference： [1]Heterocycles,2003,vol. 60,p. 2669 - 2675

19
[ 6433-72-3 ]
ethyl 10-methyl-5-oxo-5,10-dihydro-4H-indolo[3,2-e][1,2,3]triazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Reference： [1]Heterocycles,2003,vol. 60,p. 2669 - 2675

20
[ 6433-72-3 ]
10-methyl-5-oxo-5,10-dihydro-4H-indolo[3,2-e][1,2,3]triazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]

Reference： [1]Heterocycles,2003,vol. 60,p. 2669 - 2675

21
[ 6433-72-3 ]
[ 654675-14-6 ]

Reference： [1]Heterocycles,2003,vol. 60,p. 2669 - 2675

22
[ 6433-72-3 ]
3-(ethoxycarbonyl)-1H-indole-2-diazonium chloride [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2001,vol. 84,p. 2212 - 2219

23
[ 6433-72-3 ]
[ 254907-82-9 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5464 - 5474

24
[ 6433-72-3 ]
[ 254907-81-8 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5464 - 5474

25
[ 6433-72-3 ]
[ 171179-93-4 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5464 - 5474

26
[ 6433-72-3 ]
(3-bromo-phenyl)-(2-methyl-9H-1,3,9-triaza-fluoren-4-yl)-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5464 - 5474

27
[ 6433-72-3 ]
2-Amino-4-(3-bromoanilino)indolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5464 - 5474

28
[ 6433-72-3 ]
4-chloro-1H-pyrimido[4,5-b]indole-2-amine hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 5464 - 5474

29
[ 6433-72-3 ]
diethyl 1H-imidazo<1,2-a>indole-3,9-dicarboxylate [ No CAS ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 745 - 754

30
[ 6433-72-3 ]
1-Ethoxycarbonylmethyl-2-methoxymethyleneamino-1H-indole-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 745 - 754

31
[ 2727-71-1 ]
[ 105-56-6 ]
[ 6433-72-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 1035 - 1038

32
[ 143321-89-5 ]
[ 105-56-6 ]
[ 6433-72-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 1035 - 1038

33
[ 615-43-0 ]
[ 6433-72-3 ]

Reference： [1]Synthesis,2011,p. 764 - 768

34
[ 10113-39-0 ]
[ 105-56-6 ]
[ 6433-72-3 ]

Reference： [1]Synthesis,2011,p. 764 - 768

35
C₁₆H₁₆O [ No CAS ]
[ 6433-72-3 ]
[ 1324007-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In acetonitrile; for 6h;Reflux; Inert atmosphere;	General procedure: To a degassed solution of Pd(PPh3)2Cl2 (0.02 equiv), CuI (0.04 equiv), TEA (1.25 equiv), in CH3CN (5.0 mL) was added benzoyl chloride (1.0 equiv, 1a-d) and terminal alkyne (1.0 equiv, 2a-d) under N2 atmosphere and the reaction was stirred at rt for 1 h. After formation of alkynone as monitored on tlc, <strong>[6433-72-3]ethyl 2-amino-1H-indole-3-carboxylate</strong> (1.0 equiv, 3a-d) and Cs2CO3 (1.5 equiv) were sequentially added to the reaction mixture and was refluxed for 6 h. The crude reaction mixture was filtered through a bed of celite, washed, and extracted with ethyl acetate (3 × 10 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure in vacuo. The crude reaction mixture was purified by column chromatography on 60-120 mesh silica using EtOAc/hexane (1:19) as eluent to afford 4a-r.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 4288 - 4291

36
[ 20442-65-3 ]
[ 6433-72-3 ]
[ 1324007-09-1 ]

Yield	Reaction Conditions	Operation in experiment
0.238 g	With caesium carbonate; In acetonitrile; for 6h;Reflux; Inert atmosphere;	General procedure: To a degassed solution of Pd(PPh3)2Cl2 (0.02 equiv), CuI (0.04 equiv), TEA (1.25 equiv), in CH3CN (5.0 mL) was added benzoyl chloride (1.0 equiv, 1a-d) and terminal alkyne (1.0 equiv, 2a-d) under N2 atmosphere and the reaction was stirred at rt for 1 h. After formation of alkynone as monitored on tlc, <strong>[6433-72-3]ethyl 2-amino-1H-indole-3-carboxylate</strong> (1.0 equiv, 3a-d) and Cs2CO3 (1.5 equiv) were sequentially added to the reaction mixture and was refluxed for 6 h. The crude reaction mixture was filtered through a bed of celite, washed, and extracted with ethyl acetate (3 × 10 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure in vacuo. The crude reaction mixture was purified by column chromatography on 60-120 mesh silica using EtOAc/hexane (1:19) as eluent to afford 4a-r.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 4288 - 4291

37
[ 65418-72-6 ]
[ 6433-72-3 ]
[ 1324007-12-6 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In acetonitrile; for 6h;Reflux; Inert atmosphere;	General procedure: To a degassed solution of Pd(PPh3)2Cl2 (0.02 equiv), CuI (0.04 equiv), TEA (1.25 equiv), in CH3CN (5.0 mL) was added benzoyl chloride (1.0 equiv, 1a-d) and terminal alkyne (1.0 equiv, 2a-d) under N2 atmosphere and the reaction was stirred at rt for 1 h. After formation of alkynone as monitored on tlc, <strong>[6433-72-3]ethyl 2-amino-1H-indole-3-carboxylate</strong> (1.0 equiv, 3a-d) and Cs2CO3 (1.5 equiv) were sequentially added to the reaction mixture and was refluxed for 6 h. The crude reaction mixture was filtered through a bed of celite, washed, and extracted with ethyl acetate (3 × 10 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure in vacuo. The crude reaction mixture was purified by column chromatography on 60-120 mesh silica using EtOAc/hexane (1:19) as eluent to afford 4a-r.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 4288 - 4291

38
[ 6433-72-3 ]
[ 16616-43-6 ]
[ 1324007-11-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In acetonitrile; for 6h;Reflux; Inert atmosphere;	General procedure: To a degassed solution of Pd(PPh3)2Cl2 (0.02 equiv), CuI (0.04 equiv), TEA (1.25 equiv), in CH3CN (5.0 mL) was added benzoyl chloride (1.0 equiv, 1a-d) and terminal alkyne (1.0 equiv, 2a-d) under N2 atmosphere and the reaction was stirred at rt for 1 h. After formation of alkynone as monitored on tlc, <strong>[6433-72-3]ethyl 2-amino-1H-indole-3-carboxylate</strong> (1.0 equiv, 3a-d) and Cs2CO3 (1.5 equiv) were sequentially added to the reaction mixture and was refluxed for 6 h. The crude reaction mixture was filtered through a bed of celite, washed, and extracted with ethyl acetate (3 × 10 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure in vacuo. The crude reaction mixture was purified by column chromatography on 60-120 mesh silica using EtOAc/hexane (1:19) as eluent to afford 4a-r.

Reference： [1]Synthetic Communications,2013,vol. 43,p. 2090 - 2099
[2]Tetrahedron Letters,2011,vol. 52,p. 4288 - 4291

39
[ 6433-72-3 ]
[ 5719-08-4 ]

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6123 - 6133,11

40
[ 6433-72-3 ]
[ 1403589-26-3 ]

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6123 - 6133,11

41
[ 6433-72-3 ]
[ 1403589-33-2 ]

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6123 - 6133,11

42
[ 6433-72-3 ]
[ 1403589-40-1 ]

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6123 - 6133,11

43
[ 6433-72-3 ]
[ 77287-34-4 ]
3H-pyrimido[4,5-b]indole-4(9H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium methylate; at 220℃; for 1.5h;	Step 3. Synthesis of 3H-pyrimido[4,5 [formula 12-4]Ethyl-2-aminotlH-indo 3-carboxyate [foHnula -2-3]-(8-g 39rl-72 mmol) and sodium" methoxide (2.116 g, 39.172 mmol) was dissolved in formamide (40 mL) and stirred at 220C for an hour and half. Then the reaction mixture was filtered with adding water at room temperature. The filtered substance was dried to yield the title compound as black solid (0.92 g, 78%).
78%	With sodium methylate; at 220℃; for 1.5h;	(8 g, 39.172 mmol) and sodium methoxide (2.116 g, 39.172 mmol) was dissolved in formamide (40 mL) and stirred at 220 C. for an hour and half. Then the reaction mixture was filtered with adding water at room temperature. The filtered substance was dried to yield the title compound as black solid (0.92 g, 78%).
15.8 g	at 190℃;	3.5. 6-Chloro-3H-pyrimido[4,5-b]indol-4(9H)-one (9): Indole derivative 7 (30 g, 126 mmol) was dissolved in formamide (100 ml, 2.5 mol) and after heating to 190 C for 18 h reaction mixture was cooled down, filtered, washed well with water and dried under reduced pressure. Compound 9 (23.6 g, 85%) was obtained as dark powder. The crude compound was purified by column chromatography (chloroform/MeOH, 3% MeOH); mp: 188-193C. IR (ATR): m = 2924, 1661, 1588, 1447, 1359, 1250, 794 cm-1. 1H NMR (600.1 MHz, DMSO-d6): 7.34 (ddd, 1H, J7,8 = 8.6, J7,5 = 2.2, J7,NH = 0.4, H-7); 7.49 (ddd, 1H, J8,7 = 8.6, J8,5 = 0.6, J8,NH = 0.4, H-8); 7.91 (ddt, 1H, J5,7 = 2.2, J5,8 = 0.6, J5,NH = 0.4, H-5); 8.16 (bd, 1H, J2,NH = 3.5, H-2), 12.31 (br s, 1H, NH-3); 12.36 (br s, 1H, NH-9). 13C NMR (150.9 MHz, DMSO-d6): 99.9 (C-4a); 113.5 (CH-8); 119.7 (CH-5); 123.4 (C-4b); 124.2 (CH-7); 125.6 (C-6); 134.1 (C-8a); 148.4 (CH-2); 154.6 (C-9a); 158.3 (C-4). ESI MS m/z (rel.%): 242 (100) [M+Na], 244 (33) [M+2+Na]. HR MS (ESI) for C10H6ClN3ONa [M+Na]: calcd 242.00916; found 242.00915. 3.6. 3H-Pyrimido[4,5-b]indol-4(9H)-one (10) :Compound 10 was prepared as described for 9 from crude 8 (20.0 g, 108 mmol) to give 15.8 g, (87%) of 10 as dark powder.The crude compound was directly used in the next step. For analysis,the crude compound was further purified by column chromatography(chloroform/MeOH, 3% MeOH); mp: >300 C. IR (ATR):m = 3031, 2359, 2342, 1640, 1587, 1541, 1377, 1248, 750 cm-1. 1H NMR (500.0 MHz, DMSO-d6): 7.23 (ddd, 1H, J6,5 = 7.9, J6,7 = 7.2,J6,8 = 1.0, H-6); 7.32 (ddd, 1H, J7,8 = 8.2, J7,6 = 7.2, J7,5 = 1.2, H-7);7.48 (ddd, 1H, J8,7 = 8.2, J8,6 = 1.0, J8,5 = 0.8, H-8); 7.99 (ddt, 1H,J5,6 = 7.9, J5,7 = 1.2, J5,8 = J5,NH = 0.8, H-5); 8.12 (s, 1H, H-2), 12.17,12.20 (2 br s, 2 1H, NH). 13C NMR (125.7 MHz, DMSO-d6):100.4 (C-4a); 111.9 (CH-8); 120.9 (CH-5); 121.4 (CH-6); 122.3 (C-4b); 124.4 (CH-7); 135.7 (C-8a); 147.7 (CH-2); 153.9 (C-9a); 158.6 (C-4). ESI MS m/z (rel.%): 186 (12) [M+H], 208 (100) [M+Na]. HR MS (ESI) for C10H7N3ONa [M+Na]: calcd 208.04813; found 208.04815.

Reference： [1]Patent: WO2013/62344,2013,A1 .Location in patent: Page/Page column 28; 99; 100
[2]Patent: US2014/315889,2014,A1 .Location in patent: Paragraph 0474-0478
[3]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6123 - 6133,11

44
[ 105-56-6 ]
[ 6433-72-3 ]

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6123 - 6133,11
[2]Patent: US2014/315889,2014,A1
[3]Patent: WO2013/62344,2013,A1

45
[ 88-73-3 ]
[ 6433-72-3 ]

Reference： [1]Bioorganic and medicinal chemistry,2012,vol. 20,p. 6123 - 6133,11

46
[ 1493-27-2 ]
[ 6433-72-3 ]

Reference： [1]Patent: US2014/315889,2014,A1
[2]Patent: WO2013/62344,2013,A1

47
[ 6433-72-3 ]
[ 1432509-70-0 ]

Reference： [1]Patent: US2014/315889,2014,A1
[2]Patent: WO2013/62344,2013,A1

48
[ 6433-72-3 ]
[ 1432508-53-6 ]

Reference： [1]Patent: US2014/315889,2014,A1
[2]Patent: WO2013/62344,2013,A1

49
[ 104-87-0 ]
[ 6433-72-3 ]
[ 766-97-2 ]
ethyl 2-(4-methylphenyl)-4-[4-(methylphenyl)]pyrimido[1,2-a]indole-10-carboxylate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6057 - 6066

50
[ 104-87-0 ]
[ 6433-72-3 ]
[ 766-97-2 ]
[ 1350516-27-6 ]
ethyl 2-(4-methylphenyl)-4-[4-(methylphenyl)]pyrimido[1,2-a]indole-10-carboxylate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6057 - 6066

51
[ 104-87-0 ]
[ 6433-72-3 ]
[ 536-74-3 ]
[ 1324007-09-1 ]
2-(4-methylphenyl)-4-phenyl-9H-pyrido[2,3-b]indole [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6057 - 6066

52
[ 772-38-3 ]
[ 104-87-0 ]
[ 6433-72-3 ]
[ 1350516-28-7 ]
ethyl 4-[4-(tert-butyl)phenyl]-2-(4-methylphenyl)pyrimido[1,2-a]-indole-10-carboxylate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6057 - 6066

53
[ 772-38-3 ]
[ 104-87-0 ]
[ 6433-72-3 ]
ethyl 4-[4-(tert-butyl)phenyl]-2-(4-methylphenyl)pyrimido[1,2-a]-indole-10-carboxylate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6057 - 6066

54
[ 104-88-1 ]
[ 6433-72-3 ]
[ 536-74-3 ]
2-(4-chlorophenyl)-4-phenyl-9H-pyrido[2,3-b]indole [ No CAS ]
ethyl 2-(4-chlorophenyl)-4-phenylpyrimido[1,2-a]indole-10-carboxylate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6057 - 6066

55
[ 772-38-3 ]
[ 104-88-1 ]
[ 6433-72-3 ]
ethyl 4-[4-(tert-butyl)phenyl]-2-(4-chlorophenyl)pyrimido[1,2-a]-indole-10-carboxylate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6057 - 6066

56
[ 772-38-3 ]
[ 6433-72-3 ]
[ 1122-91-4 ]
ethyl 2-(4-bromophenyl)-4-[4-(tert-butyl)phenyl]pyrimido[1,2-a]-indole-10-carboxylate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6057 - 6066

57
[ 772-38-3 ]
[ 555-16-8 ]
[ 6433-72-3 ]
ethyl 4-[4-(tert-butyl)phenyl]-2-(4-nitrophenyl)pyrimido[1,2-a]-indole-10-carboxylate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6057 - 6066

58
[ 73179-67-6 ]
[ 6433-72-3 ]
7-phenyl-6,8-dihydrochromeno[3',4':5,6]pyrido[3,2-b]indole [ No CAS ]
ethyl 7-phenyl-6H-chromeno[4',3':4,5]pyrimido[1,2-a]indole-13-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2020,vol. 22,p. 1117 - 1123
[2]Organic Letters,2020,vol. 22,p. 1117 - 1123

59
4-methoxy-2-((3-phenylprop-2-yn-1-yl)oxy)benzaldehyde [ No CAS ]
[ 6433-72-3 ]
3-methoxy-7-phenyl-6,8-dihydrochromeno[3',4':5,6]pyrido[3,2-b]indole [ No CAS ]