145901-11-7|1H-Pyrrolo[2,3-b]pyridin-6-amine| Ambeed

Structure of 145901-11-7

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 145901-11-7 ] Purity: 97% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 145901-11-7 ]

CAS No. :	145901-11-7
Formula :	C₇H₇N₃
M.W :	133.15
SMILES Code :	NC1=CC=C2C(NC=C2)=N1
MDL No. :	MFCD08272224
InChI Key :	OHPOAAFCWFZVPF-UHFFFAOYSA-N
Pubchem ID :	10419227

Safety of [ 145901-11-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Computational Chemistry of [ 145901-11-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	2.0
Molar Refractivity	40.5
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.7 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.02
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.96
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.15
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.78
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.36
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.05

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.94
Solubility	1.54 mg/ml ; 0.0116 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.7
Solubility	2.68 mg/ml ; 0.0201 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.52
Solubility	0.404 mg/ml ; 0.00303 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.43 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.44

Application In Synthesis of [ 145901-11-7 ]

* 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 [ 145901-11-7 ]

[ 145901-11-7 ] Synthesis Path-Downstream 1~35

1
[ 143468-13-7 ]
[ 145901-11-7 ]

References: [1]Bulletin of the Chemical Society of Japan,1992,vol. 65,p. 2992 - 2997.

2
[ 145901-11-7 ]
[ 99-63-8 ]
N,N'-bis(1H-pyrrolo<2,3-b>pyridin-6-yl)-1,3-benzenedicarboxamide [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1992,vol. 65,p. 2992 - 2997.

3
[ 108-24-7 ]
[ 145901-11-7 ]
N-(1-acetyl-1H-pyrrolo[2,3-b]pyridin-6-yl)acetamide [ No CAS ]

References: [1]Patent: US6335342,2002,B1 .Location in patent: Example 1.

4
6-azaindole-N-oxide m-chlorobenzoate [ No CAS ]
[ 145901-11-7 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of O-methyl-nu-oxide salt intermediate in AcCN (10 ml) obtained as above from 1.37 g (4.71 mmol) N-oxide m-CBA salt and dimethylsulfate (0.49 ml, 1.05 eq.) was added a solution OfNH3 in dry MeOH (7M, Aldrich, 15 ml) under cooling in an icebath. The brown mixture was stirred in a sealed vial at 70 0C overnight. After evaporation of the solvent and aq. workup as above, the crude was purified by silica gel chromatography to give a light-brown, cryst. solid. HR-MS calculated for [MH]+: 134.07127, found: 134.07150.

References: [1]Patent: WO2007/48070,2007,A2 .Location in patent: Page/Page column 138.

5
CH₃O₄S^(1-)*C₇H₅ClO₂*C₈H₉N₂O⁽¹⁺⁾ [ No CAS ]
[ 145901-11-7 ]

References: [1]Synthesis,2008,p. 201 - 214.

6
[ 271-63-6 ]
[ 145901-11-7 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of commercially available 7-azaindole (5 g, 42.3 mmol) in diethyl ether (350 mL) was added m-chloro perbenzoic acid (11 g, 63.4 mmol) in portions at room temperature. The reaction mixture was stirred at room temperature for 5 h. The precipitated product was filtered off and washed with diethyl ether (50 mL). The solid was collected and dissolved in a mixture of water/acetone (50 mL/10 mL) with heating. The mixture was cooled to 5 C. and the crystallized product was filtered and air dried to afford the title compound (11.7 g, 96%).1H-NMR (400 MHz, CDCl3): delta=6.59 (d, 1H), 7.07 (dd, 1H), 7.46 (d, 1H), 7.66 (d, 1H), 8.14 (d, 1H), 12.4 (s, 1H).Step BTo a suspension of the title compound from Step A above (2 g, 6.92 mmol) in dry acetonitrile (15 mL) was added dimethylsulfate (0.885 g, 6.92 mmol). The reaction mixture was heated at 70 C. for 8 h. Then the clear solution was cooled to room temperature. The solution was distributed in three sealed tubes and cooled to 0 C. under an argon atmosphere. Then a 7 M solution of ammonia in methanol (5 mL) was added to each tube. The sealed tubes were heated at 50-60 C. for 48 h. The solvent was removed and the residue was dissolved in ethyl acetate (200 mL) and the organic phase was washed with dilute Na2CO3 solution, water, and brine. The organic phase was dried over Na2SO4. The solvent was evaporated and the crude product was purified by chromatography on silica using ethyl acetate to afford the title compound (0.5 g, 54%).1H-NMR (400 MHz, CDCl3): delta=4.33 (m, 2H), 6.35 (dd, 1H), 6.38 (d, 1H), 6.99 (dd, 1H), 7.71 (d, 1H).

References: [1]Patent: US2011/256064,2011,A1 .
[2]Patent: US2011/280808,2011,A1 .Location in patent: Page/Page column 40.
[3]Patent: US2013/178478,2013,A1 .
[4]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1405 - 1411.
[5]Patent: EP2377860,2011,A1 .
[6]Patent: WO2011/128455,2011,A1 .
[7]Patent: CN108997343,2018,A .

7
1H-pyrrolo[2,3-b]pyridine 1-oxide meta-chlorobenzoic acid salt [ No CAS ]
[ 145901-11-7 ]

Yield	Reaction Conditions	Operation in experiment
54%		To a suspension of the compound from Step A above (2 g, 6.92 mmol) in dry acetonitrile (15 mL) was added dimethylsulfate (0.885 g, 6.92 mmol). The reaction mixture was heated at 70 C. for 8 hours. Then the clear solution was cooled to room temperature. The solution was distributed in three sealed tubes and cooled to 0 C. under an argon atmosphere. Then a 7 M solution of ammonia in methanol (5 mL) was introduced in each tube. The tubes were sealed. The sealed tubes were heated at 50 to 60 C. for 48 h. The solvent was removed and the residue was dissolved in ethyl acetate (200 mL) and the organic phase was washed with dilute Na2CO3 solution, water, and brine. The organic phase was dried over Na2SO4. The solvent was evaporated and crude product was purified on silica gel (ethyl acetate) to give the title compound (0.5 g, 54%).1H-NMR (400 MHz, CDCl3): =7.71 (d, 1H), 6.99 (dd, 1H), 6.38 (d, J=8.4 Hz, 1H), 6.35 (dd, 1H), 4.33 (m, 2H).
54%		Step B To a suspension of the compound from Step A above (2 g, 6.92 mmol) in dry acetonitrile (15 mL) was added dimethylsulfate (0.885 g, 6.92 mmol). The reaction mixture was heated at 70 C for 8 hours. Then the clear solution was cooled to room temperature. The solution was distributed in three sealed tubes and cooled to 0 C under an argon atmosphere. Then a 7 M solution of ammonia in methanol (5 mL) was introduced in each tube. The tubes were sealed. The sealed tubes were heated at 50 to 60 C for 48 h. The solvent was removed and the residue was dissolved in ethyl acetate (200 mL) and the organic phase was washed with dilute Na2CO3 solution, water, and brine. The organic phase was dried over Na2SO4. The solvent was evaporated and crude product was purified on silica gel (ethyl acetate) to give the title compound (0.5 g, 54 %). 1H-NMR (400 MHz, CDCl3): delta = 7.71 (d, 9H), 6.99 (dd, 1H), 6.38 (d, J = 8.4Hz, 1H), 6.35 (dd, 1H), 4.33 (m, 2H)
54%		Step B; To a suspension of the title compound from Step A above (2 g, 6.92 mmol) in dry acetonit ie (15 mL) was added dimethylsulfate (0.885 g, 6.92 mmol). The reaction mixture was heated at 70 C for 8 h. Then the clear solution was cooled to room temperature. The solution was distributed in three sealed tubes and cooled to 0 C under an argon atmosphere. Then a 7 M solution of ammonia in methanol (5 mL) was added to each tube. The sealed tubes were heated at 50-60 C for 48 h. The solvent was removed and the residue was dissolved in ethyl acetate (200 mL) and the organic phase was washed with dilute Na2C03 solution, water, and brine. The organic phase was dried over Na2S04. The solvent was evaporated and the crude product was purified by chromatography on silica using ethyl acetate to afford the title compound (0.5 g, 54%).1H-NMR (400 MHz, CDCI3): delta = 4.33 (m, 2H), 6.35 (dd, 1 H), 6.38 (d, 1 H), 6.99 (dd, 1 H), 7.71 (d, 1 H).

48%	With dimethyl sulfate; In acetonitrile;Reflux;	The suspension of compound 3 (1.89g, 11.8 mmol) in dry CH3CN (15 ml) was added dimethylsulfate and heated the reaction mixture at 80 C for overnight. The reaction mixture was cooled to room temperature. Then, the reaction mixture was partitioned into 3 sealed tubes and cooled to ice bath temperature. The 7N NH3 solution in MeOH (5 ml) was introduced to each tube at 0 C temperature and sealed the tubes. The reaction mixture was heated at 70 C for 2d. The reaction mixture was concentrated under reduced pressure and the residue was crystallized from ethyl acetate and heptane mixture to give compound 5 (0.9 g, 48%). 1H-NMR (400 MHz, CDCl3): delta= 7.83 (s, 1H), 7.64 (d, J = 8.4Hz, 1H), 6.42 (d, J = 8.8Hz, 1H), 6.00 (s, 1H) 3.33 (bs, 2H).
44.6%		Under nitrogen atmosphere in anhydrous acetonitrile 1H-pyrrolo[2,3-b]pyridine-N-oxide meta-chlorobenzoic acid (12.3 g, 42.5mmol) and dimethyl sulfate (4.5 ml, 46.3 mmol) the suspension was 55-60 C It was stirred for 14 hours in . The reaction mixture was transferred to a sealed tube was cooled to 0 ~ 4 was slowly added a solution of ammonia (7M, 100 ml) in methanol. The reaction mixture was stirred at 50 ~ 55 C for 24 hours. Distilled off and the solvent of the reaction and extracted with dichloromethane (100 ml) and 10% aqueous potassium carbonate solution (25 ml) to the remaining residue and the water layer was further extracted three times with dichloromethane (50ml). All the organic layer was removed with 10% carbonate kalryul solution and saturated brine, washed with water once and the solvent collecting behind a dry, filtered over anhydrous magnesium sulfate filtrate. The residue was purified by silica gel chromatography (ethyl acetate: petroleum ether = 1: 2) to afford the title compound as a yellow crystalline solid (2.5g, 44.6% yield).
316 mg		Step 4 1H-Pyrrolo[2,3-b]pyridin-6-ylamine 1H-Pyrrolo[2,3-b]pyridine 7-oxide, 3-chlorobenzoic acid complex (1.5 g, 5.16 mmol) was suspended in acetonitrile (10 mL). Dimethyl sulfate (0.54 mL, 5.68 mmol) was added and the reaction mixture was warmed to 60 C. After 16 h, the mixture was transferred to a thick-walled pressure tube and 7M ammonia in methanol solution (11 mL) was added. The tube was sealed and warmed to 55 C. After 16 h, the solvent was evaporated and the residue was taken up in dichloromethane and 10% sodium carbonate solution. The aqueous layer was extracted with dichloromethane, and then the combined organic layers were washed successively with saturated aqueous sodium bicarbonate solution, water and brine. The organic phase was dried (sodium sulfate), filtered, and concentrated in vacuo. Purification by chromatography (silica, 10 to 80% ethyl acetate in hexanes) gave 1H-pyrrolo[2,3-b]pyridin-6-ylamine (316 mg, 46%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.73 (br. s., 1H) 7.70 (d, J=8.3 Hz, 1H) 6.99 (d, J=3.5 Hz, 1H) 6.38 (d, J=8.3 Hz, 1H) 6.36 (d, J=3.5 Hz, 1H) 3.82 (br. s., 2H).

References: [1]Patent: US2011/256064,2011,A1 .Location in patent: Page/Page column 23; 24.
[2]Patent: EP2377860,2011,A1 .Location in patent: Page/Page column 31.
[3]Patent: WO2011/128455,2011,A1 .Location in patent: Page/Page column 86.
[4]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1405 - 1411.
[5]Patent: KR101560536,2015,B1 .Location in patent: Paragraph 0116-0118.
[6]Patent: US2013/178478,2013,A1 .Location in patent: Paragraph 0256.

8
[ 1015609-27-4 ]
[ 145901-11-7 ]
[ 1342811-66-8 ]

Yield	Reaction Conditions	Operation in experiment
30%	With sodium t-butanolate; In 1,4-dioxane; at 110℃; for 2h;Inert atmosphere;	Preparative Example 60; Step AStep AAn oven-dried Schlenk flask was evacuated and back filled with argon gas. The procedure was repeated for 3-4 times. At room temperature dioxane (3 ml_) was added by a syringe and degassed by bubbling argon through the mixture. Then 2-dicyclohexylphosphino-2',4',6'- triisopropylbiphenyl (XPhos, 0.054 g, 0.1 12 mmol) and palladium(ll) acetate (0.009 g, 0.037mmol) were added together. The mixture was heated at 110 C for 1 minute. The reaction mixture became a clear red color solution. Then the title compound from Preparative Example 3 (0.050 g, 0.375 mmol), commercially available 6-bromo-1-(triisopropylsilyl)-1 /-/-pyrrolo[3,2- £>]pyridine (0.132 g, 0.375 mmol) and sodium tert butoxide (0.12 g, 1.25 mmol) were added together under an argon atmosphere. The reaction mixture was heated at 110 C for 2 h. The reaction mixture was diluted with ethyl acetate (150 mL). The organic phase was washed with water, brine, and was dried over Na2S04. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate to afford the title compound (0.045 g, 30 %). H-NMR (400 MHz, CDCI3): delta = 1.13 (d, 18H), 1.61-1.68 (m, 3H), 6.35 (dd, 1H), 6.60 (d, 1H), 6.80 (d, 1H), 6.94 (dd, 1H), 7.10 (brs, 1H), 7.39 (d, 1H), 7.73 (d, 1H), 8.20 (s, 1H), 8.54 (s, 1H), 9.27 (s, 2H)
30%	With sodium t-butanolate; XPhos;palladium diacetate; In 1,4-dioxane; at 110℃; for 2h;Inert atmosphere;	An oven-dried Schlenk flask was evacuated and back filled with argon gas. The procedure was repeated for 3-4 times. At room temperature dioxane (3 mL) was added by a syringe and degassed by bubbling argon through the mixture. Then 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos, 0.054 g, 0.112 mmol) and palladium(II) acetate (0.009 g, 0.037 mmol) were added together. The mixture was heated at 110 C. for 1 minute. The reaction mixture became a clear red color solution. Then the title compound from Preparative Example 3 (0.050 g, 0.375 mmol), commercially available 6-bromo-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridine (0.132 g, 0.375 mmol) and sodium tert butoxide (0.12 g, 1.25 mmol) were added together under an argon atmosphere. The reaction mixture was heated at 110 C. for 2 h. The reaction mixture was diluted with ethyl acetate (150 mL). The organic phase was washed with water, brine, and was dried over Na2SO4. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate to afford the title compound (0.045 g, 30%).1H-NMR (400 MHz, CDCl3): delta=1.13 (d, 18H), 1.61-1.68 (m, 3H), 6.35 (dd, 1H), 6.60 (d, 1H), 6.80 (d, 1H), 6.94 (dd, 1H), 7.10 (brs, 1H), 7.39 (d, 1H), 7.73 (d, 1H), 8.20 (s, 1H), 8.54 (s, 1H), 9.27 (s, 2H)
30%	With palladium diacetate; sodium t-butanolate; XPhos; In 1,4-dioxane; at 110℃; for 2h;Inert atmosphere;	An oven-dried Schlenk flask was evacuated and back filled with argon gas. The procedure was repeated for 3-4 times. At room temperature dioxane (3 mL) was added by a syringe and degassed by bubbling argon through the mixture. Then 2-dicyclohexylphosphino-2?,4?,6?-triisopropylbiphenyl (XPhos, 54 mg, 0.112 mmol) and palladium(II) acetate (9 mg, 0.037mmol) were added together. The mixture was heated at 110 oC for 1 minute. The reaction mixture became a clear red color solution. Then compound 5 (50 mg, 0.375 mmol), commercially available 6-bromo-1-(triisopropylsilyl)-1H-pyrrolo[3,2-b]pyridine 31 (132 mg, 0.375 mmol) and sodium tert butoxide (120 mg, 1.25 mmol) were added together under an argon atmosphere. The reaction mixture was heated at 110 oC for 2 h. The reaction mixture was diluted with ethyl acetate (150 mL). The organic phase was washed with water, brine, and was dried over Na2SO4. The solvent was removed and the residue was purified by chromatography on silica using ethyl acetate to afford the compound 38a (45 mg, 30 %). 1H-NMR (400 MHz, CDCl3): delta = 9.27 (s, 2H), 8.54 (s, 1H), 8.20 (s, 1H), 7.73 (d, 1H), 7.39 (d, 1H), 7.10 (br-s, 1H), 6.94 (dd, 1H), 6.80 (d, 1H), 6.60 (d, 1H), 6.35 (dd, 1H), 1.68-1.61 (m, 3H), 1.13 (d, 18H).

References: [1]Patent: WO2011/128455,2011,A1 .Location in patent: Page/Page column 176-177.
[2]Patent: US2011/280808,2011,A1 .Location in patent: Page/Page column 87.
[3]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1405 - 1411.

9
[ 1403888-69-6 ]
[ 145901-11-7 ]
[ 1403886-21-4 ]

References: [1]Patent: WO2012/143143,2012,A1 .

10
[ 1403888-69-6 ]
[ 145901-11-7 ]
C₂₆H₂₂N₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example No. 130Preparation of (8-Methoxy-2H-pyrazolo [3, 4-c] quinolin-4 -yl) - (IH-pyrrolo [2 , 3 -b] pyridin-6-yl) -amineIH-pyrrolo [2 , 3 -b] pyridin-6-amine (0.4 mmol 2 eq.,) was dissolved in THF (dry, 3mL) in a microwave vial (2-5mL) LiHMDS 2M in THF (0.6 mmol 4eq.) was added. The mixture was stirred for 20 min at r.t. and then added to a solution of 4-chloro-8- methoxy-2- (4 -methoxybenzyl) -2H-pyrazolo [3 , 4-c] quinoline (0.16 mmol, leq.) in pyridine (2mL) . The reaction mixture was irradiated in a microwave reactor for 20 min at 200C. The reaction mixture was evaporated and used without further purification. The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140 C. The reaction mixture was concentrated and purified by semi -preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 330.1404 g/molHPLC-MS : analytical method Brt: 2.352 min - found mass: 331.1 (m/z+H)

References: [1]Patent: WO2012/143143,2012,A1 .Location in patent: Page/Page column 242-243.

11
[ 145901-11-7 ]
[ 1446791-69-0 ]

References: [1]Patent: US2013/178478,2013,A1 .
[2]Patent: KR101560536,2015,B1 .

12
[ 145901-11-7 ]
[ 1446791-71-4 ]

References: [1]Patent: US2013/178478,2013,A1 .

13
[ 145901-11-7 ]
[ 1446791-72-5 ]

References: [1]Patent: US2013/178478,2013,A1 .

14
[ 145901-11-7 ]
[ 1446791-74-7 ]

References: [1]Patent: US2013/178478,2013,A1 .

15
[ 145901-11-7 ]
[ 1446790-54-0 ]

References: [1]Patent: US2013/178478,2013,A1 .

16
[ 85-44-9 ]
[ 145901-11-7 ]
[ 1446791-65-6 ]

Yield	Reaction Conditions	Operation in experiment
78.7%	With acetic acid; for 3h;Reflux;	Glacial acetic acid (10 ml) to 1H- pyrrolo [2,3-b] pyridin-6-amine (0.8 g, 6.0 mmol) phthalic anhydride (0.90 g dissolved in the solution,It was added to 6.1 mmol) and stirred under reflux for 3 hours. Remove the solvent by vacuum distillation and the reaction was neutralized by adding slowly an aqueous solution of sodium bicarbonate was not until the end of the foam occurs the residue. Collecting the formed solid by filtration and vacuum dried to a washing with water to give the title compound (1.4 g, 78.7% yield).
75%	With sodium acetate; In acetic acid; at 120℃; for 3h;	Step 5 2-(1H-pyrrolo[2,3-b]pyridin-6-yl)-isoindole-1,3-dione 1H-Pyrrolo[2,3-b]pyridin-6-ylamine (0.12 g, 0.9 mmol) was suspended in acetic acid (1.5 mL), then phthalic anhydride (133 mg, 0.9 mmol) and sodium acetate (118 mg, 1.44 mmol) were added and the mixture heated to 120 C. After 3 h, the mixture was concentrated in vacuo, the residue obtained dissolved in ethyl acetate, and then cooled to 0 C. Ice-water and sodium bicarbonate solution were added then the aqueous layer was extracted with ethyl acetate. The aqueous layer was adjusted to pH 6 with 1M HCl solution and was extracted twice more with ethyl acetate. The combined organic layers were dried over sodium sulfate then concentrated in vacuo. Purification by chromatography (silica, 20 to 70% ethyl acetate in hexanes) gave 2-(1H-pyrrolo[2,3-b]pyridin-6-yl)-isoindole-1,3-dione (179 mg, 75%) as a light brown solid. 1H NMR (300 MHz, DMSO-d6) delta ppm 11.91 (br. s., 1H) 8.15 (d, J=7.9 Hz, 1H) 7.90-8.05 (m, 4H) 7.59-7.65 (m, 1H) 7.21 (d, J=7.9 Hz, 1H) 6.54-6.60 (m, 1H); LCMS (EI/CI) m/z: 264 [M+H].
40.46%	With sodium acetate; acetic acid; at 120℃; for 5h;	To a solution of 19.1 (0.5 g, 3.75 mmol, 1.0 equiv) and NaOAc (0.49 g, 6.00 mmol, 1 equiv) in acetic acid (5 mL) was added phtalic anhydride (0.667 g, 4.5 mmol, 1.2 equiv) and stirred at 120 C. for 5 hours. Reaction mixture was poured into water (50 mL) and extracted with EtOAc (20 mL*3). Organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure to obtain crude material. Crude was stirred in aqueous satd. NaHCO3, filtered then dried to get pure 21.1 (0.400 g, 40.46%). MS (ES): m/z 264.3 [M+H]+.

References: [1]Patent: KR101560536,2015,B1 .Location in patent: Paragraph 0165-0168.
[2]Patent: US2013/178478,2013,A1 .Location in patent: Paragraph 0256.
[3]Patent: US2016/251376,2016,A1 .Location in patent: Paragraph 0523; 0524; 0525.

17
[ 1603-40-3 ]
[ 145901-11-7 ]

References: [1]Patent: US2013/178478,2013,A1 .

18
[ 138343-75-6 ]
[ 145901-11-7 ]

References: [1]Patent: US2013/178478,2013,A1 .

19
[ 145901-11-7 ]
[ 1446791-67-8 ]

References: [1]Patent: US2013/178478,2013,A1 .
[2]Patent: KR101560536,2015,B1 .

20
[ 90-02-8 ]
[ 145901-11-7 ]
[ 1575392-39-0 ]

References: [1]ChemMedChem,2014,vol. 9,p. 73 - 77.

21
4-oxo-1,4-dihydroquinoline-3-carbonyl chloride [ No CAS ]
[ 145901-11-7 ]
4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1H-pyrrolo[2,3-b]pyridin-6-yl)amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 9776 - 9795.

22
[ 145901-11-7 ]
5-chloro-3-methylbenzo[b]thiophene-2-sulfonyl chloride [ No CAS ]
5-chloro-3-methyl-N-(1H-pyrrolo[2,3-b]pyridin-6-yl)benzo[b]thiophene-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13.4%	With pyridine; at 20℃; for 2h;	Pyridine (10 ml) for 5-chloro-3-methyl-benzo [b] thiophene-2-sulfonyl chloride (1.5 g, 5.3 mmol) in a mixed solution was added to1H- pyrrolo [2,3-b] pyridine-6-amine (0.91 g, 6.8 mmol) and stirred for 2 hours at room temperature. The reaction by TLCDetermine whether the termination of the above reaction mixture was concentrated and the residue was purified by silica gel chromatography (ethyl acetate: petroleumEther = 1: 8) to afford the title compound as a white solid (270 mg, 13.4% yield).

References: [1]Patent: KR101560536,2015,B1 .Location in patent: Paragraph 0141; 0142; 0151; 0152.

23
[ 89108-45-2 ]
[ 145901-11-7 ]
5-chloro-N-(1H-pyrrol[2,3-b]pyridin-6-yl)naphthalene-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	With pyridine; at 20℃; for 3h;	Pyridine (10 ml) was added a 5-chloro-naphthalene-2-sulfonyl chloride dissolved in a solution of a blood 1H- pyrrolo [2,3-b] pyridin-6-amine (1.0g) and stirred for 3 hours at room temperature . Determine whether the termination of the reaction by TLC and concentrate the above reaction mixture and the residue was purified by silica gel chromatography (ethyl acetate: petroleum ether = 1: 1) to give the title compoundIt was obtained (220 mg, overall 7.0% yield).

References: [1]Patent: KR101560536,2015,B1 .Location in patent: Paragraph 0155; 0156; 0161; 0162.

24
[ 1623-93-4 ]
[ 145901-11-7 ]
N-(1H-pyrrolo[2,3-b]pyridin-6-yl)[1,1'-biphenyl]-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.6%	With pyridine; at 20℃; for 2h;	Pyridine (10 ml) to <strong>[145901-11-7]1H-pyrrolo[2,3-b]pyridin-6-amine</strong>(266 mg, 2 mmol) in a mixed solution was added [1,1'-biphenyl]-4-sulfonyl chloride It was added (500 mg, 2 mmol) and stirred for 2 hours at room temperature. The reaction mixture was concentrated and the residue was purified by graph silica gel (ethyl acetate: petroleum ether = 1: 2) to afford the title compound as a white solid (500 mg, 71.6% yield).

References: [1]Patent: KR101560536,2015,B1 .Location in patent: Paragraph 0115; 0116; 0119-0120.

25
[ 145901-11-7 ]
4-(4-cyanophenyl)-N-(1H-pyrrolo[2,3-b]pyridin-6-yl)(piperidinyl)-1-sulfonamide [ No CAS ]

References: [1]Patent: KR101560536,2015,B1 .

26
[ 145901-11-7 ]
4'-cyano-N-{1-methyl-1H-pyrrolo[2,3-b]pyridin-6-yl}[1,1'-biphenyl]-4-sulfonamide [ No CAS ]

References: [1]Patent: KR101560536,2015,B1 .

27
[ 1189-71-5 ]
[ 145901-11-7 ]
[ 107-07-3 ]
N-(1H-pyrrolo[2,3-b]pyridin-6-yl)-2-oxo-oxazolidin-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%		Dichloromethane (100 ml) to chlorosulfonyl isocyanate (0.87 ml, 0.01 mol) dissolved in a mixed solution to 0Cin 2-Chloroethanol (0.67 ml, 0.01 mol) was slowly added.After stirring for 1.5 hours the reaction mixture at 0 Cin dichloromethane (120 ml) 1H-pyrrolo [2,3-b] pyridin-6-amine (1.33 g, 0.01 mol) and triethylamine (4.2 ml, 0.03 mol) dissolved in the solution and the reaction temperature for 5Cto maintain and was added slowly. The temperature of the reaction mixture slowly raised to room temperature and stirred for 24 hours.The reaction was then concentrated and the residue washed with a small amount of dichloromethane and filtered to give the title compound as a white solid (1.3 g, 46% yield).

References: [1]Patent: KR101560536,2015,B1 .Location in patent: Paragraph 0133-0136.

28
[ 149506-86-5 ]
[ 145901-11-7 ]
4'-cyano-N-(1H-pyrrolo[2,3-b]pyridin-6-yl)[1,1'-biphenyl]-4-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67.8%	With pyridine; at 20℃;	In pyridine (10 ml) 4'-cyano-[1,1'-biphenyl]-4-sulfonyl chloride(70 mg, 0.5 mmol) was dissolved in a solution <strong>[145901-11-7]1H-pyrrolo[2,3-b]pyridin-6-amine</strong>(140 mg, 0.5 mmol) to It was added and stirred for 4 hours at room temperature. Check the completion of the reaction, whether by TLC, and the residue was purified by silica gel chromatography by concentration of the above reaction mixture: Purification of (ethyl acetate petroleum ether = 1: 2) to give the title compound as a white solid (67.8 mg, 67.8% yield).

References: [1]Patent: KR101560536,2015,B1 .Location in patent: Paragraph 0123; 0124; 0129; 0130.

29
C₂₂H₁₇ClF₂N₂O₃ [ No CAS ]
[ 145901-11-7 ]
4-(6-amino-1H-pyrrolo[2,3-b]pyridin-1-yl)-2-(2,6-difluorophenyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one [ No CAS ]