808744-34-5|7-Bromoimidazo[1,2-a]pyridine| Ambeed

Structure of 808744-34-5

*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 [ 808744-34-5 ] Purity: 95% 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 [ 808744-34-5 ]

CAS No. :	808744-34-5
Formula :	C₇H₅BrN₂
M.W :	197.03
SMILES Code :	BrC1=CC2=NC=CN2C=C1
MDL No. :	MFCD07778353
InChI Key :	OASOJRLJBDCVNU-UHFFFAOYSA-N
Pubchem ID :	15098903

Safety of [ 808744-34-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 808744-34-5 ] 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	0.0
Molar Refractivity	42.89
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.94
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	2.45
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.1
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.	1.48
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	1.67
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.93

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.27
Solubility	0.106 mg/ml ; 0.000536 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.46
Solubility	0.688 mg/ml ; 0.00349 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-2.94
Solubility	0.225 mg/ml ; 0.00114 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.	-5.76 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)	1.66

Application In Synthesis of [ 808744-34-5 ]

* 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 [ 808744-34-5 ]

[ 808744-34-5 ] Synthesis Path-Downstream 1~35

2
[ 421-17-0 ]
[ 808744-34-5 ]
3-trifluoromethylsulfanyl-5-bromoimidazol{1,2a}pyridine hydrochloride [ No CAS ]

References: [1]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: F: PerFHalOrg.SVol.2, 6.2.1.6.4.2, page 117 - 172.
[2]Patent: DE2820938,1978, .
Chem.Abstr.,vol. 90.

3
[ 808744-34-5 ]
[ 1692-25-7 ]
[ 1067914-66-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; acetonitrile; at 60℃; for 18h;	Step B: Preparation of 7-(pyridin-3-yl)imidazori.2-a1pyridine:; A suspension of potassium carbonate (0351 g, 2.54 mmol), pyridin-3-ylboronic acid (68.6 mg5 0.558 mmol), 7- bromoimidazo[l52-a]pyridine (0.100 g, 0.508 mmol) and tetrakis(triphenylphosphine) <n="70"/>palladium (0) (29.3 mg, 0.025 mmol) in 6.5 ml of a 1:1 :4.5 mixture of water:dimethylformamide:acetonitrile was degassed thoroughly under a nitrogen atmosphere, and heated at 60 0C for 18 hours. The reaction mixture was poured in water (50 ml) and extracted with dichloromethane and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford a solid. The solid was purified by silica gel chromatography (eluting with 6% MeOH-chloroform) to afford the desired compound (74.1 mg, 75 % yield). MS APCI (+) m/z 196.3 (M+l) detected.
75%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; acetonitrile; at 60℃; for 18h;	A suspension of potassium carbonate (0.351 g, 2.54 mmol), pyridine-3-ylboronic acid (68.6 mg, 0.558 mmol), 7-bromoimidazo[l,2-a] pyridine (0.100 g, 0.508 mmol) and tetrakis(triphenylphosphine) palladium (0) (29.3 mg, 0.025 mmol) in 6.5 ml of a 1:1 :4.5 mixture of water:dimethylformamide:acetonitrile was degassed thoroughly under a nitrogen atmosphere, and heated at 60 C for 18 hours. The reaction mixture was poured in water (50 ml) and extracted with dichloromethane and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford a solid. The solid was purified by silica gel chromatography (eluting with 6% MeOH-chloroform) to afford the desired compound (74.1 mg, 75 % yield). MS APCI (+) m/z 196.3 (M+l) detected.

References: [1]Patent: WO2008/124323,2008,A1 .Location in patent: Page/Page column 68-69.
[2]Patent: WO2008/121687,2008,A2 .Location in patent: Page/Page column 53.

4
[ 107-20-0 ]
[ 84249-14-9 ]
[ 808744-34-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	In water; at 100℃; for 4h;	To a suspension of 4-bromopyridin-2-amine (5.26 g, 30.40 mmol) in water (50 mL) was added 2-chloroacetaldehyde (40% [w/w] in water, 15.24 g, 77.66 mmol). The reaction mixture was stirred at 100 C for 4 h, and adjusted to pH = 10 with a saturated Na2CO, aqueous solution, then extracted with DCM (100 mL c 3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v) = 1/100) to give the title compound as yellow oil (5.93 g, yield 100%).MS (ESI, pos. ion) m/z: 197.2 [M+H]+;1H NMR (400MHz, CDCl3) d (ppm): 8.00 (d, j = 7.2 Hz, 1H), 7.82 (d, J = 0.8 Hz, 1H), 7.61 (s, 1H), 7.57 (s, 1H), 6.90 (dd, j= 7.2, 1.7 Hz, 1H).
100%	In water; at 100℃; for 4h;	To 4-bromopyridin-2-amine (5.26 g, 30.40 mmol)In water (50mL) suspension2-chloroacetaldehyde (40% [w/w] in water, 15.24 g, 77.66 mmol).The reaction mixture was stirred at 100 C for 4 hours.After the reaction,Adjust to pH=10 with a saturated aqueous solution of sodium carbonate.It was then extracted with dichloromethane (100 mL x 3).The combined organic phases were washed with saturated brine (100 mL).Dry over anhydrous sodium sulfate,Filter and concentrate under reduced pressure.The residue obtained is purified by silica gel column chromatography (MeOH/DCM (v/v) = 1/100).The title compound was obtained as a yellow liquid (5.93 g, yield 100%).
78%	With sodium hydrogencarbonate; In ethanol; for 6h;Reflux;	The compound 2-amino-4-bromopyridine 22 (5.0 g) and 2-chloroacetaldehyde (40%solution, 12 mL, 2.5 eq) was dissolved in absolute ethanol (50 mL)After addition of NaHCO3 (4.89 g, 2.0 eq)Reflux reaction 6h.The organic solvent was removed by vacuum filtration, washed with EA (60 mL), washed with water, saturated with brine, dried over Na2SO4 and dried on a dry column to give brown solid 23 (4.38 g, 78%).

71%		Example 44; 8-(ftrans)-3-fluoropiperidin-4-yloxy)-2-(7-(pyridin-3-yl)imidazo[1.2-a]pyridin-3-yl)qiotaiotainoluie; Step A: Preparation of 7-bromoimidazo[1.2-a]pyridine:; A solution of 4- bromopyridin-2-amine (1.00 g, 5.78 mmol) and 2-chloroacetaldehyde (50% wt aqueous solution, 1.83 ml5 14.45 mmol) in absolute ethanol (9.5 ml) was refluxed for 12 hours, and then allowed to cool to ambient temperature overnight. The reaction mixture was concentrated under reduced pressure and carefully re-suspended in saturated aqueous bicarbonate solution (100 ml). The resulting mixture was extracted thoroughly with DCM and EtOAc, and the combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford 1.31 g of a solid. The solid was purified by silica gel chromatography (eluting with 3% MeOH-chloroform) to afford the desired compound (0.808 g5 71 % yield). MS APCI (+) m/z 197.1 and 199.1 (M+l for each isotope) detected.
71%	In ethanol; water; at 20℃; for 12h;Heating / reflux;	A solution of 4- bromopyridin-2-amine (1.00 g, 5.78 mmol) and 2-chloroacetaldehyde (50% wt aqueous solution, 1.83 ml, 14.45 mmol) in absolute ethanol (9.5 ml) was refluxed for 12 hours, and then allowed to cool to ambient temperature overnight. The reaction mixture was concentrated under reduced pressure and carefully re-suspended in saturated aqueous bicarbonate solution (100 ml). The resulting mixture was extracted thoroughly with DCM and EtOAc, and the combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford 1.31 g of a solid. The solid was purified by silica gel chromatography (eluting with 3% MeOH-chloroform) to afford the desired compound (0.808 g, 71 % yield). MS APCI (+) m/z 197.1 and 199.1 (M+l for each isotope) detected.
63%	With sodium hydrogencarbonate; In ethanol; for 16h;Reflux;	To a stirred solution of 4-bromopyridin-2-amine (5 g, 28.9 mmol, Molekula Biokem Ltd) in EtCH (5OmL), added sodium bicarbonate (7.28 g, 86.7 mmol) and chloroacetaldehyde (5 mL, 115 mmol) and refluxed for 16 h. The reaction mixture was evaporated under vacuum and water (25 mL) was added to the crude mixture. The resulting solution was extractedwith EtOAc (2 x 50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated. The resulting crude product was purified by flash chromatography. Yield:63% (3.6 g, brown solid). LCMS: (Method B) 199.0 (M +H), Rt. 3.92 mm, 94.50% (Max).
63%	With sodium hydrogencarbonate; In ethanol; for 16h;Reflux;	To a stirred solution of 4-bromopyridin-2-amine (5 g, 28.9 mmol, Molekula Biokem Ltd) in EtOH (50ml_), added sodium bicarbonate (7.28 g, 86.7 mmol) and chloroacetaldehyde (5 mL, 1 15 mmol) and refluxed for 16 h. The reaction mixture was evaporated under vacuum and water (25 mL) was added to the crude mixture. The resulting solution was extracted with EtOAc (2 x 50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated. The resulting crude product was purified by flash chromatography. Yield: 63% (3.6 g, brown solid). LCMS: (Method B) 199.0 (M +H), Rt. 3.92 min, 94.50% (Max).
	With sodium hydrogencarbonate; In ethanol; for 17h;Heating / reflux;	4-Bromo-pyridin-2-ylamine (1 eq, 5.78 mmol, 1 g) is added to a solution of chloroacetic aldehyde (5 eq, 28.9 mmol, 5 ml) in EtOH (25 ml). NaHCO3 (2 eq, 11.6 mmol, 971 g) is then added and the reaction mixture is heated at reflux for 17 h. The solvent is then removed in vacuo and the product is purified by flash column chromatography eluting with 9:1 DCM/MeOH to afford 7-bromo-imidazo-[1,2-a]- pyridine as a brown solid; [M+H]+ = 198
		INTERMEDIATE SYNTHESIS; 7-bromo-3-iodoimidazo[ 1 ,2-a]pyridine; (1) 7-bromoimidazo[l,2-a]pyridine.; To a 100 niL round -bottomed flask was added 4-bromopyridin-2-amine (4.0 g, 23.1 mmol), chloroacetaldehyde, 50% in water (14.9 rnL, 116 mmol), and EtOH (25 mL). The resulting reaction mixture was heated at 100 0C under N2 for 3 h. The reaction was cooled to rt and the solvent was concentrated. The residue was redissolved in EtOAc. The organic layer was washed with sat. NaHCObeta (2 x 40 mL), water (2 x 40 mL), brine, dried over MgSO4, and removed solvent. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep, 12O g SiO2, DCM:MeOH=96%:4% to DCM:MeOH (2M NH3)=95%:5%, Flow = 85 niL/min). The solvent was removed in vacuo to afford the desired product as brown solid (3.8 g). MS (ESI pos. ion) m/z: 196.8. Calcd exact mass for C7H5BrN2: 195.9. 1U NMR (300 MHz, CHLOROFORM-J) delta ppm 6.90 (d, J=7.16 Hz, 1 H) 7.57 (s, 1 H) 7.62 (s, 1 H) 7.83 (s, 1 H) 8.00 (d, J=7.16 Hz, 1 H).
18.6 g	In ethanol; water; at 0℃;Reflux;	The compound 2-amino-4-bromopyridine 6 (20.00 g, 116.28 mmol) was dissolved in a mixture of ethanol (300 mL) and water (30 mL).After stirring for 20 minutes under ice bath conditions, when the solution temperature drops to 0 C,40% chloroacetaldehyde (28.60 mL, 174.40 mmol) was added slowly and stirred at reflux overnight.The mixture was filtered with Celite, and then evaporated and evaporated.Washed with water, washed with saturated brine, dried with Na2SO4 and then driedColumn chromatography gave a brown solid 8 (18.60 g, 81%).

References: [1]Patent: WO2019/99311,2019,A1 .Location in patent: Paragraph 000366.
[2]Patent: CN109776522,2019,A .Location in patent: Paragraph 0586; 0599; 0600; 0601; 0602.
[3]Patent: CN106496222,2017,A .Location in patent: Paragraph 0095; 0097.
[4]Patent: WO2008/124323,2008,A1 .Location in patent: Page/Page column 68.
[5]Patent: WO2008/121687,2008,A2 .Location in patent: Page/Page column 53.
[6]Patent: WO2017/144633,2017,A1 .Location in patent: Page/Page column 101; 102.
[7]Patent: WO2017/144639,2017,A1 .Location in patent: Page/Page column 87.
[8]Patent: WO2009/50183,2009,A2 .Location in patent: Page/Page column 116.
[9]Patent: WO2010/108074,2010,A2 .Location in patent: Page/Page column 62-63.
[10]Patent: CN110003202,2019,A .Location in patent: Paragraph 0116; 0122-0125.

5
[ 808744-34-5 ]
[ 17997-47-6 ]
[ 908267-70-9 ]

Yield	Reaction Conditions	Operation in experiment
39%	With triethylamine;tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 100℃; for 17h;	A solution of7-bromoimidazo[l,2-a]pyridine (0.100 g, 0.508 mmol), tri-o-tolylphosphine, tris(dibenzylideneacetone)dipalladium(0) (47 mg, 0.051 mmol), and 2-tri-n- butylstannylpyridine (0.234 g, 0.508 mmol) in anhydrous DMF (5 ml) was combined at ambient temperature under a nitrogen atmosphere with triethylamine (65 mg, 0.65 mmol). The reaction mixture was heated at 100 0C for 17 hours. The reaction mixture was then allowed to cool, poured in water (40 ml), and extracted with DCM, ether, and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford a solid. The solid was purified by silica gel chromatography (eluting with 5% MeOH-DCM) to afford the desired compound (38.4 mg, 39% yield). MS APCI (+) m/z 196.3 (M+l) detected

References: [1]Patent: WO2008/121687,2008,A2 .Location in patent: Page/Page column 54.

6
[ 808744-34-5 ]
[ 847818-74-0 ]
[ 1036761-86-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate;bis(tri-t-butylphosphine)palladium(0); In ethanol; water; toluene; at 75℃; for 2h;	Procedure B1c - Suzuki coupling for heterocvcles.; A solution of 7-Bromo-imidazol[1 ,2-a]pyridine (0.5g, 2.54mmol, 1 equivalent, made according to general procedure A1 using 4-bromo-pyridin-2-ylamine instead of 4-chloro-pyridin-2- ylamine) , 1 -methyl-5-(4,4, 5, 5-tetramethyl-[ 1 , 3, 2]dioxaborolan-2-yl)- 1 H-py razole ( 1.1 g, 5.08mmol, 2 equivalents), bis(tri-t-butylphosphine) palladium (0) (66mg, 0.13mmol, 0.05 equivalents) and potassium carbonate (2.1g, 15.24mmol, 6 equivalents) in ethanol (10ml), toluene (10ml) and water (10ml) was heated at 750C for 2 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was then washed with a saturated brine solution, dried (MgSO4), filtered and the solvent removed by evaporation in vacuo. The residue was purified by column chromatography (Biotage SP4, 25S, flow rate 25ml/min, gradient 0% to 20% methanol in ethyl acetate) to give 7-(2-methyl-2H-pyrazol-3-yl)- imidazo[1 ,2,a]pyridine as a colourless oil (350mg, 70%). MS: [M+H]+ 199.

References: [1]Patent: WO2008/78100,2008,A2 .Location in patent: Page/Page column 97-98.

7
3-(methylcarbamoyl)phenylboronic acid [ No CAS ]
[ 808744-34-5 ]
[ 1146615-82-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 120℃; for 0.166667h;Microwave radiation;	7-Bromo-imidazo-[1,2-a]-pyridine (1 eq, 0.5 mmol, 100 mg) and (3-methylamino carbonylphenyl)boronic acid (1.1 eq, 0.558 mmol, 99.9 mg) are dissolved in DME (3 ml) and water (0.8 ml) and Na2CO3 (3 eq, 1.52 mmol, 161 mg) is added. PdCl2(PPh3)I (0.05 eq, 0.025 mmol, 17.8 mg) is then added and the reaction mixture is heated using microwave radiation at 120C for 10 min. At the completion of this time the solvent is removed in vacuo and the reaction mixture is purified by flash column chromatography eluting with 9:1 DCM/MeOH to yield 3-imidazo[1,2-a]pyridine-7-yl- N-methyl-benzamide as a brown solid; [M+H]+ = 252

References: [1]Patent: WO2009/50183,2009,A2 .Location in patent: Page/Page column 117.

8
[ 808744-34-5 ]
[ 1246184-55-3 ]

Yield	Reaction Conditions	Operation in experiment
86.9%	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 100℃; for 1h;	To a solution of 7-bromoimidazo[l,2-a]pyridine (5.93 g, 30.1 mmol) in DMF (60 mL) was added NIS (9.19 g, 40.8 mmol). The reaction mixture was stirred at 100 C for 1 hour, then cooled down to rt and quenched with water (50 mL), then extracted with DCM (100 mL x 3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/10) to give the title compound as a yellow solid (8.45 g, yield 86.9%).MS (ESI, pos. ion) m/z: 323.0 [M+H]+;1H NMR (400 MHz, CDCl3) d (ppm): 8.02 (d, J= 7.3 Hz, 1H), 7.83 (d, J= 1.2 Hz, 1H), 7.69 (s, 1H), 7.05 (dd, j= 7.3, 1.7 Hz, 1H).
86.9%	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 100℃; for 1h;	To <strong>[808744-34-5]7-bromoimidazo[1,2-a]pyridine</strong> (5.93 g, 30.1 mmol)Add in DMF (60mL) solutionNIS (9.19 g, 40.8 mmol).The reaction mixture was stirred at 100 C for 1 hour.Then cool to room temperature,The reaction was quenched by the addition of water (50 mL).It was then extracted with DCM (100 mL x 3).Combined organic phase with saturated brine (100 mL)Washed, dried over anhydrous sodium sulfate,Filter and concentrate under reduced pressure.The residue obtained was purified by silica gel column chromatography (EtOAc /EtOAcThe title compound was obtained as a white solid (8.45 g, yield 86.9%).
	With iodine; sodium acetate; In methanol; at 0℃;	(2) 7-bromo-3-iodoimidazo[l,2-a]pyridine.; To a 250 mL round bottomed flask was added 7-bromoimidazo[l,2-a]pyridine (3.8 g, 19.29 mmol), sodium acetate (4.3 g, 52.1 mmol) and MeOH (60 mL). The resulting mixture was cooled to 0 0C followed by adding diiodine (8.3 g, 32.8 mmol). After the addition, ice bath was removed and the mixture was continued to stir for 5 h. The solvent was concentrated. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep, 330 g SiO2, hexanes:acetone= 80%:20%, Flow = 100 mL/min). The solvent was removed in vacuo to afford the desired product as light yellow solid (3.2 g). (ESI pos. ion) m/z: 322.8. Calcd exact mass for C7H4BrIN2: 321.9. 1H NMR (300 MHz, CHLOROFORM-^) delta ppm 7.04 (d, J=7.02 Hz, 1 H) 7.68 (s, 1 H) 7.82 (s, 1 H) 8.01 (d, J=7.31 Hz, I H).

References: [1]Patent: WO2019/99311,2019,A1 .Location in patent: Paragraph 000399.
[2]Patent: CN109776522,2019,A .Location in patent: Paragraph 0737; 0739; 0740; 0741; 0742.
[3]Patent: WO2010/108074,2010,A2 .Location in patent: Page/Page column 63.

9
[ 808744-34-5 ]
[ 1276022-88-8 ]
[ 1276023-79-0 ]

Yield	Reaction Conditions	Operation in experiment
58.4%	With rac-diaminocyclohexane; cesium fluoride;copper(l) iodide; In 1,4-dioxane; at 95℃;Inert atmosphere;	1 equiv. of the oxazolidin-2-one was given together with <strong>[808744-34-5]7-bromoimidazo[1,2-a]pyridine</strong> (1 equiv.), cesium fluoride (2 equiv.) and copper(I) iodide (0.1 equiv.) in a flask. The flask was purged with argon and a solution of cyclohexane-1,2-diamine (0.1 equiv.) in dioxane was added. The reaction was stirred at 95 C. until TLC indicated consumption of the oxazolidin-2-one. After cooling to 45 C. the reaction mixture was filtered through a pad of CELITE, the pad was washed with warm dichloromethane and the solution was concentrated under reduced pressure. The final product was purified via FPLC using a chloroform-methanol gradient (0?10%). Step D:Product obtained from step C (0.376 g, 1.7 mmol), <strong>[808744-34-5]7-bromoimidazo[1,2-a]pyridine</strong> (0.335 g, 1.7 mmol), copper(I) iodide (0.033 g, 0.17 mmol), cesium fluoride (0.52 g, 3.4 mmol), cyclohexane-1,2-diamine (0.021 mL, 0.17 mmol), yield: 0.335 g (58.4%)Overall yield: 8.7%; MS m/z 338.2 (M+H)+; 1H NMR (400 MHz, DMSO-D6): delta 0.92 (t, 3H, J=7.5 Hz); 1.62-1.70 (m, 2H); 3.83-3.87 (m, 2H); 4.12-4.16 (m, H); 4.80-4.84 (m, H); 5.71-5.74 (m, H); 6.89 (d, 2H, J=8.7); 7.26 (d, H, J=7.5 Hz); 7.31-7.38 (m, 3H); 7.48 (br s, H); 7.83 (br s, H); 8.46 (br s, H), HPLC (lambda=214 nm), [B]: rt 11.20 min (95%).

References: [1]Patent: US2011/92501,2011,A1 .Location in patent: Page/Page column 90; 120-121.

10
[ 808744-34-5 ]
[ 1276023-75-6 ]
[ 1276023-83-6 ]

Yield	Reaction Conditions	Operation in experiment
31.3%	With potassium carbonate; rac-diaminocyclohexane;copper(l) iodide; In 1,4-dioxane; at 95℃;Inert atmosphere;	1 equiv. of the 1,3-oxazinan-2-one was given together with <strong>[808744-34-5]7-bromoimidazo[1,2-a]pyridine</strong> (1 equiv.), potassium carbonate (2 equiv.) and copper(I) iodide (0.1 equiv.) in a flask. The flask was purged with argon and a solution of cyclohexane-1,2-diamine (0.1 equiv.) in dioxane was added. The reaction was stirred at 95 C. until TLC indicated consumption of the 1,3-oxazinan-2-one. After cooling to 45 C. the reaction mixture was filtered through a pad of CELITE, the pad was washed with warm dichloromethane and the solution was concentrated under reduced pressure. The final product was purified via FPLC using a chloroform-methanol gradient (0?10%). Step D:Product obtained from step C (0.45 g, 1.91 mmol), <strong>[808744-34-5]7-bromoimidazo[1,2-a]pyridine</strong> (0.376 g, 1.91 mmol), copper(I) iodide (0.036 g, 0.19 mmol), potassium carbonate (0.528 g, 3.82 mmol), cyclohexane-1,2-diamine (0.023 mL, 0.19 mmol), yield: 0.210 g (31.3%)Overall yield: 6.1%; MS m/z 352.3 (M+H)+; 1H-NMR (400 MHz, DMSO-d6): delta 0.87-0.91 (m, 3H); 1.58-1.67 (m, 2H); 2.05-2.12 (m, H); 2.49-2.57 (m, H); 3.79-3.82 (m, 2H); 4.20-4.26 (m, H); 4.35-4.40 (m, H); 5.45-5.47 (m, H); 6.81 (d, 2H, J=8.7 Hz); 7.24 (d, 2H, J=8.7 Hz); 7.47 (d, H, J=7.9 Hz); 7.75 (s, H); 7.96 (s, H); 8.10 (s, H); 8.65 (d, H, J=7.9 Hz), HPLC (lambda=214 nm), [B]: rt 9.73 min (100%).

References: [1]Patent: US2011/92501,2011,A1 .Location in patent: Page/Page column 92; 121.

11
[ 808744-34-5 ]
3-(4-bromophenyl)-4-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-4H-1,2,4-triazole [ No CAS ]
7-[4-(4-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-4H-1,2,4-triazol-3-yl)phenyl]imidazo[1,2-a]pyridin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%		Example 687-[4-(4- [(35)- 1 -(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl} -4H- 1 ,2,4-triazol-3- yl)phenyl]imidazo[ 1 ,2-a]pyridinA mixture of 7-bromoimidazo[l,2-a]pyridine (125 mg, 0.634 mmol),£zs(pinacolato)diboron (180 mg, 0.709 mmol), KOAc (250 mg, 2.55 mmol), andPdCl2(dppf) (50 mg, 0.061 mmol) in 1,4-dioxane (3 mL) was stirred at 100 C. 3-(4- Bromophenyl)-4- { [(35)- 1 -(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl} -4H- 1 ,2,4-triazole (230 mg, 0.613 mmol) and 2 M aq. K2C03 (1.5 mL) were added and the reaction mixture was stirred at 100 C overnight. The 1,4-dioxane layer was removed, passed through a plug of Celite and Na2S04, rinsed with 1,4-dioxane (4 mL), and the organic layers concentrated in vacuo. Purification of the residue by reverse phase HPLC (5-45%CH3CN/water with 0.1% TFA), reverse phase HPLC (10-70% CH3CN/water with 0.1% NH4OH), and then reverse phase HPLC (2-40% MeOH/water with 0.08% NH4OH) provided the title compound (36 mg, 13%). MS(ES)+ m/e 413.3 [M+H]+.

References: [1]Patent: WO2012/37298,2012,A1 .Location in patent: Page/Page column 90-91.

12
[ 808744-34-5 ]
1-[1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(trifluoromethyl)-1H-benzimidazole [ No CAS ]
1-[1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2-(4-imidazo[1,2-a]pyridin-7-ylphenyl)-5-(trifluoromethyl)-1H-benzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 100℃; for 2h;Inert atmosphere; Sealed vial;	Example 145l-[(3S)-l-(Cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2-(4-imidazo[l,2-fl]pyridin- 7-ylphenyl)-5-(trifluoromethyl)-lH-benzimidazole2-(4-Bromophenyl)- 1 - { [(3 S)- 1 -(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl} -5- (trifluoromethyl)-lH-benzimidazole (82 mg, 0.167 mmol) was dissolved in 1,4-dioxane (1.5 mL) in 5-mL microwave vial. Potassium acetate (44.8 mg, 0.457 mmol),4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-l,3,2-dioxaborolane (42.5 mg, 0.167 mmol), andPdCl2(dppf)-CH2Cl2 adduct (6.22 mg, 7.61 umol) were then added with stirring. The vial was purged with nitrogen, sealed, and heated to 100 C for 2 hours. The reaction mixture was allowed to cool to room temperature. 7-Bromoimidazo[l,2-a]pyridine (30 mg, 0.152 mmol), PdCl2(dppf)-CH2Cl2 adduct (6.22 mg, 7.61 umol) and 2 M aqueous potassium carbonate (0.228 mL, 0.457 mmol) were then added. The vial was again purged with nitrogen, sealed and heated at 100 C for 2 hours. The reaction mixture was allowed to cool to room temperature, diluted with water (50 mL), acidified to pH 7 with 1 N HC1, and extracted with DCM (3 x 50 mL). The combined DCM extracts were dried over sodium sulfate and evaporated to dryness. The resulting crude product was dissolved in DMSO and purified by preparative reverse phase hplc. The appropriate fractions were combined and the pH adjusted to 7 with aqueous sodium bicarbonate (saturated) and extracted with DCM (3 x 25 mL). The combined DCM extracts were dried over sodium sulfate and evaporated to dryness to afford 22 mg of the titled compound. (LCMS m/z 529.9, M+H).

References: [1]Patent: WO2011/56635,2011,A1 .Location in patent: Page/Page column 132.

13
[ 808744-34-5 ]
(S)-(N-3-(3-fluoro-4-(3,3,4,4-tetramethylborolan-1-yl)phenyl)-2-oxo-5-oxazolidinyl)methylacetamide [ No CAS ]
[ 1202701-98-1 ]

References: [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 1074 - 1078.

14
[ 808744-34-5 ]
(R)-3-(3-fluoro-4-(3,3,4,4-tetramethylborolan-1-yl)phenyl)-5-([1,2,3]triazol-1-yl)methyloxazolidin-2-one [ No CAS ]
[ 1202703-04-5 ]

References: [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 1074 - 1078.

15
[ 808744-34-5 ]
[ 1534371-07-7 ]

References: [1]Patent: WO2014/8223,2014,A2 .

16
[ 808744-34-5 ]
[ 73183-34-3 ]
[ 908268-52-0 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90℃; for 18h;Sealed tube; Inert atmosphere; Microwave irradiation;	In a sealed microwave vial purged with nitrogen, a mixture of 7-bromoimidazo[l,2- ajpyridine (50 mg, 0.254 mmol), bis(pinacolato)diboron (66 mg, 0.260 mmol), potassium acetate (70 mg, 0.713 mmol), and l,l'-bis(diphenylphosphino)ferrocene- palladium(II)dichloride dichloromethane complex (10 mg, 0.012 mmol) in 1,4-dioxane (2 mL) was stirred at 90 C for 18 h to give the boronic ester intermediate, 7-(4 ,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)imidazo[l,2-a]pyridine. The reaction mixture was cooled to room temperature. 9-[(4-bromo-2-fluorophenyl)methyl]-4-cyclopropyl-l-oxa-4,9- diazaspiro[5.5]undecan-3-one (100 mg, 0.237 mmol), l,l'-bis(diphenylphosphino)ferrocene- palladium(II)dichloride dichloromethane complex (10 mg, 0.012 mmol) and 2M aqueous potassium carbonate solution (1 mL, 2 mmol) were added to the reaction mixture and the resulting mixture was stirred at 100 C for 1 h. The reaction was cooled to room temperature, diluted with ethyl acetate (20 mL) and water (5 mL), and the layers were separated. The aqueous layer was extracted with ethyl acetate (20 mL). The organic layers were combined, dried over MgSC^, and concentrated in vacuo. Purifications by silica gel chromatography (0- 10% methanol/ethyl acetate) followed by reverse phase HPLC (10-70% acetonitrile /water + 0.1% NH4OH) provided the title compound as a beige solid (16 mg, 16%). MS(ES)+ m/e 435.1 [M+H]+.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90℃; for 2h;Inert atmosphere;	A mixture of <strong>[808744-34-5]7-bromoimidazo[1,2-a]pyridine</strong> (40 mg, 0.164 mmol), (0842) 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (40 mg, 0.136 mmol), KOAc (93 mg, 0.34 mmol) and Pd(dppf)Cl2.DCM (14 mg, 0.019 mmol) in dioxane (2 mL) was stirred at 90 oC for 2 h under N2 atmosphere. The reaction was concentrated in vacuo and the crude mixture of 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine was used in the next step without purification. LC-MS m/z: 245.2 [M+H]+. tR = 1.17 min.

References: [1]Patent: WO2014/8223,2014,A2 .Location in patent: Page/Page column 58-59.
[2]Patent: WO2017/176961,2017,A1 .Location in patent: Paragraph 00516.

17
[ 808744-34-5 ]
1,3,3-trimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one [ No CAS ]
6-(imidazo[1,2-a]pyridin-7-yl)-1,3,3-trimethylindolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
244 mg	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere;	b) 6-(Imidazo[1,2-a]pyridin-7-yl)-1,3,3-trimethylindolin-2-one Through a suspension of 1,3, 3-trimethyl-6-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)indolin- 2-one (300 mg, 896 imol), 7-bromoimidazo[1,2-alpyridine (F.P. Marmsaeter et al.,W02008121687; 212 mg, 1.08 mmol) and Na2CO3 (2M, 896 tl, 1.79 mmol) in dioxane (4 ml) was bubbled argon for 5 minutes. [1,1 ?-Bis(diphenylphosphino)ferrocenel dichloropalladium(II) (32.8 mg, 44.8 imol) was added and argon was bubbled through again for 5 minutes. The reaction mixture was heated to 110 C for 12 hours. The solvent was evaporated and the residue was purified by silica gel chromatography using ethyl acetate heptane and dichloromethane methanol ammonia as eluent. The title compound was obtained as light red solid (244 mg). MS ESI (mz): 292.2 [(M+H)i.1H NMR (CDC13, 300 MHz): oe = 8.20 (dd, J=0.8, 7.1 Hz, 1H), 7.87 - 7.80 (m, 1H), 7.69 (d,J=1.2 Hz, 1H), 7.62 (s, 1H), 7.38 - 7.28 (m, 2H), 7.14 - 7.04 (m, 2H), 3.29 (s, 3H), 1.42 (s, 6H).

References: [1]Patent: WO2014/202493,2014,A1 .Location in patent: Page/Page column 48; 49.

18
[ 808744-34-5 ]
[ 896139-85-8 ]

References: [1]Journal of the American Chemical Society,2016,vol. 138,p. 13493 - 13496.

19
[ 808744-34-5 ]
[ 889865-34-3 ]
tert-butyl 4-(4-imidazo[1,2-a]pyridin-7-ylphenoxy)piperidine-1-carboxylate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		Palladium acetate (0.021 g, 0.094 mmol) and triphenylphosphine (0.10 g, 0.38 mmol) were combined in a flask in 1,4-dioxane (6.0 mL). After stirring for 30 mi DMF (5.7 g, 6.0 mL, 78 mmol), tert-butyl 4-[4-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenoxyj piperidine- 1- carboxylate (0.75 g, 1.9 mmol), 7-bromoimidazo[1,2-ajpyridine (0.44 g, 2.2 mmol) and aq. Na2CO3 (0.5 M) (12.0 mL, 6.0 mmol) were added and the flask was heated under nitrogen at 90C overnight. The mixture was diluted with water (60 mL) then extracted with EtOAc (3x50 mL). The organic extracts were combined, washed with brine (50 mL), dried over sodium sulfate filtered and concentrated in vacuo. The residue was dissolved in EtOAc (40 mL) then treated with 2M HC1 in ether (1.5 mL) with stirring. The resultant solids were collected by filtration,

References: [1]Patent: WO2016/205633,2016,A1 .Location in patent: Paragraph 00909.

20
[ 808744-34-5 ]
[ 1066-54-2 ]
7-trimethylsilanylethynylimidazo[1,2-a]pyridine [ No CAS ]