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[ CAS No. 153624-46-5 ]

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2D 3D

Chemical Structure| 153624-46-5

Chemical Structure| 153624-46-5

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Quality Control of [ 153624-46-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 153624-46-5 ]

CAS No. :	153624-46-5	MDL No. :	MFCD03427051
Formula :	C₉H₁₃BO₃	Boiling Point :	321.9°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	180.01 g/mol	Pubchem ID :	3698726
Synonyms :

Calculated chemistry of of [ 153624-46-5 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	52.37
TPSA :	49.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.6
Log Po/w (WLOGP) :	0.15
Log Po/w (MLOGP) :	0.65
Log Po/w (SILICOS-IT) :	-0.26
Consensus Log Po/w :	0.43

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.11
Solubility :	1.41 mg/ml ; 0.00781 mol/l
Class :	Soluble
Log S (Ali) :	-2.26
Solubility :	1.0 mg/ml ; 0.00556 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.85
Solubility :	2.54 mg/ml ; 0.0141 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.75

Safety of [ 153624-46-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 153624-46-5 ]

* 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.

Upstream synthesis route of [ 153624-46-5 ]
Downstream synthetic route of [ 153624-46-5 ]

[ 153624-46-5 ] Synthesis Path-Upstream 1~2

1
[ 6967-88-0 ]
[ 153624-46-5 ]

Reference： [1] Tetrahedron, 2008, vol. 64, # 2, p. 328 - 338

2
[ 121-43-7 ]
[ 6967-88-0 ]
[ 153624-46-5 ]

Reference： [1] Patent: US5514696, 1996, A,
[2] Helvetica Chimica Acta, 2012, vol. 95, # 12, p. 2680 - 2694

[ 153624-46-5 ] Synthesis Path-Downstream 1~21

1
[ 13771-68-1 ]
[ 153624-46-5 ]
[ 907945-53-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.166667h;Microwaves;	A mixture of the ethyl 5-bromo-1-benzothiophene-2-carboxylate obtained in Reference Example 7 (1.00 g), 4-isopropoxyphenyl boronic acid (2.26 g), tetrakis(triphenylphosphine)palladium (0) (402 mg), 2 M sodium carbonate aqueous solution (3.5 mL) and 1,2-dimethoxyethane (16.5 mL) was exposed to microwaves for 10 minutes at 150C. Water was added to the reaction solution, which was then extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by basic silica gel column chromatography and recrystallized from ethyl acetate-hexane to obtain ethyl 5-(4-isopropoxyphenyl)-1-benzothiophene-2-carboxylate (0.76 g) as colorless crystals. 1H-NMR (300MHz, CDCl3); δ 1.38 (6H, d, J=6.0Hz), 1.43 (3H, t, J=7.2Hz), 4.42 (2H, q, J=7.2Hz), 4.61 (1H, m), 6.99 (2H, d, J=8.7Hz), 7.56 (2H, d, J=8.7Hz), 7.66 (1H, dd, J=1.5, 8.7Hz), 7.88 (1H, d, J=8.7Hz), 8.00 (1H, d, J=1.5Hz), 8.08 (1H, s)

Reference： [1]Patent: EP1849465,2007,A1 .Location in patent: Page/Page column 82-83

2
[ 1009101-88-5 ]
[ 153624-46-5 ]
[ 1009101-90-9 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium carbonate In 1,2-dimethoxyethane; water at 85℃; for 18h; Sealed tube;	18.B Step B: 4'-Isopropoxy-N-(2-methylbut-3-vn-2-yl)biphenyl-4-sulfonamide: A mixture of 4-iodo-N-(2-methylbut-3-yn-2-yl)benzenesulfonamide (400 mg, 1.15 mmol), 4- isopropoxy phenyl boronic acid (309 mg, 1.72 mmol). Na2COs (364 mg, 3.44 mmol) and Pd(PPh3)4 (132 mg, 0.15 mmol) were combined in DME (7 mL) and water (2 mL), and the mixture was degassed by bubbling through nitrogen for 10 minutes. The reaction mixture was sealed (sealed tube) under nitrogen, and the reaction mixture was heated at 850C for 18 hours. After cooling to ambient temperature, EtOAc (80 mL) was added, and the organics were washed with saturated NaHCO3 (aq), brine, and dried (MgSO4). The solvents were removed in vacuo to give an orange gum. The product was purified by silica gel plug eluting with 4:1 hexanes/EtOAc. 4'-isopropoxy-N-(2-methylbut-3-yn-2-yl)biphenyl-4-sulfonamide was isolated as a pale yellow solid (270 mg, 66%). MS APCI (-) m/z 356 detected.

Reference： [1]Current Patent Assignee: PFIZER INC - WO2008/24784, 2008, A1 Location in patent: Page/Page column 29

3
[ 6967-88-0 ]
[ 153624-46-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 1-bromo-4-isopropoxybenzene With tert.-butyl lithium In tetrahydrofuran at -78℃; Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; Further stages.;

Reference： [1]Fukuda, Tsutomu; Sudo, Ei-ichi; Shimokawa, Kozue; Iwao, Masatomo [Tetrahedron, 2008, vol. 64, # 2, p. 328 - 338]

4
[ 16732-70-0 ]
[ 153624-46-5 ]
5-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium phosphate In ethanol; toluene at 20 - 100℃; for 24.3h;	1.a A mixture of 5-bromoindole-2-carboxylic acid ethyl ester (2 g, 7.5 mmol), 4-isopropoxyphenylboronic acid (2.72 g, 15 mmol), K3P04 (5.52 g, 26 mlnol) ; Pd(OAc)2 (85 mg, 0.38 mmol), tri-o-tolylphosphine (228 mg, 0.75 nunol), EtOH (20 ml) and toluene (10 mL) was stirred under argon for 20 min at room temperature, and then heated at 100°C for 24 h. The mixture was allowed to cool, poured into NaHC03 (aq. , sat. ) and extracted with EtOAc. The combined extracts were washed with water and brine and then dried over Na2S04. Concentration and purification by chromatography gave the sub-title compound (1.81 g, 98%).

Reference： [1]Current Patent Assignee: OREXO AB - WO2005/123674, 2005, A1 Location in patent: Page/Page column 48

5
[ 121-43-7 ]
[ 6967-88-0 ]
[ 153624-46-5 ]

Yield	Reaction Conditions	Operation in experiment
		26.A A. A. 4-(1-methylethoxy)-phenylboronic acid Compound A was prepared from 4-(1-methylethoxy)bromobenzene and trimethylborate as described for compound A of Example 21. Crystallization from ether/hexanes provided compound A as a white solid.
	With n-butyllithium Inert atmosphere;

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US5514696, 1996, A
[2]Wang, Xin; Fu, Jian-Min; Snieckus, Victor [Helvetica Chimica Acta, 2012, vol. 95, # 12, p. 2680 - 2694]

6
3'-methoxy-4'-[(2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile [ No CAS ]
[ 153624-46-5 ]
[ 6674-22-2 ]
[ 530-62-1 ]
3-(4-isopropoxyphenyl)-5-[3-methoxy-2'-(5-oxo-4,5-dihydro-1,2,4oxadiazol-3-yl)biphenyl-4-yl]methyl}-2-methyl-6-propylpyrimidin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: 3'-methoxy-4'-[(2-methyl-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile; 4-(isopropoxy)phenylboronic acid With pyridine; copper diacetate; triethylamine In dichloromethane at 1 - 30℃; for 48h; Molecular sieves 4A; Stage #2: With hydroxylamine hydrochloride; sodium hydrogencarbonate In dimethyl sulfoxide at 90℃; for 18h; Stage #3: 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole In tetrahydrofuran at 1 - 30℃; for 3h;	400.400b To a suspension of 2' -methoxy-4' - [ (2-methyl-6-oxo-4- propyl-1, 6-dihydropyrimidin-5-yl) methyl] biphenyl-2- carbonitrile (1.00 g) , (4-isopropoxyphenyl)boronic acid (1.00 g) , triethylamine (1.3 mL) , pyridine (2.5 mL) and molecular sieves 4A (2.50 g) in dichloromethane (30 mL) was added copper (II) acetate (0.98 g) and the mixture was stirred at room temperature for 2 days. The reaction mixture was diluted with ethyl acetate, the insoluble material was filtered off through celite, and the filtrate was concentrated. The residue was purified by silica gel column chromatography. The crudely purified product was added to a mixture of hydroxylammonium chloride (2.05 g) , sodium hydrogen carbonate (3.31 g) and dimethyl sulfoxide (10 mL) , which had been stirred at 400C for 30 min, and the mixture was stirred at 900C for 18 hr. The reaction mixture was allowed to cool to room temperature, ethyl acetate and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was dissolved in tetrahydrofuran (10 mL) . N, N' -carbonyldiimidazole (0.48 g) and then 1, 8-diazabicyclo [5.4.0] undec-7-ene (0.45 mL) were added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with 1 M hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound as colorless crystals (0.88 g, 58%).1H NMR (300 MHz, CDCl3) δ 1.05 (t, J = 7.5, 3H), 1.36 (d, J=6.0, 6H), 1.68-1.84 (m, 2H), 2.18 (s, 3H), 2.66-2.76 (m, 2H), 3.67 (s, 3H), 3.93 (s, 2H), 4.48-4.64 (m, IH), 6.92-7.02 (m, 4H), 7.05-7.12 (m, 3H), 7.28-7.34 (m, IH), 7.41-7.49 (m, IH), 7.53- 7.60 (m, IH), 7.81-7.86 (m, IH)

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2008/62905, 2008, A2 Location in patent: Page/Page column 891-892

7
[ 7693-52-9 ]
[ 153624-46-5 ]
[ 1033803-02-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In acetone at 110℃; for 48h;	4.a An oven dried ACE pressure tube was charged with 4-bromo-2-nitrophenol (654 mg, 3.00 mmol), 4-isopropoxyboronic acid (810 ing, 4.50 rnmol), K2CO3 (1.66 g, 12.00 mmol) Pd(OAc)2 (67 mg, 0.3 mmol) and DABCO (67 mg, 0.6 mmol). The reaction tube was purged with argon and acetone (30 mL) was added. The reaction mixture was heated at 110 0C for 48 hours. The mixture was poured in water (100 mL) and extracted with EtOAc. The combined extracts were washed with water and brine and then dried over Na2SO4. Concentration under reduced pressure and purification by chromatography afforded the sub-title compound (710 mg, 87%).

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG; OREXO AB - WO2008/71944, 2008, A1 Location in patent: Page/Page column 52

8
[ 959150-64-2 ]
[ 153624-46-5 ]
[ 1216805-45-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662

9
[ 26166-92-7 ]
[ 153624-46-5 ]
[ 1216805-57-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Methyldicyclohexylamine; sodium hydroxide In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; chemoselective reaction;

Reference： [1]Location in patent: experimental part Stewart, Scott G.; Braun, Carlos J.; Ng, Sze-Ling; Polomska, Marta E.; Karimi, Mahdad; Abraham, Lawrence J. [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 2, p. 650 - 662]

10
[ 55934-22-0 ]
[ 153624-46-5 ]
[ 1409964-05-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	In 1,4-dioxane; water	Preparation of 4-chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline Preparation of 4-chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline To a degassed solution of 2,4-dichloro-7-methoxyquinoline (1 g, 4.3 mmol) in dioxane/water (8:2) was added 4-isopropoxyphenylboronic acid (870 mg, 4.82 mmol) followed by potassium carbonate (1.2 g, 8.7 mmol) and Pd(PPh3)4 (253 mg, 0.22 mmol) at room temperature under nitrogen atmosphere. The reaction mass was heated at 90° C. for 18 h. The solvent was removed under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to afford 4-chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline (1.2 g, 85%) as off white solid. MS: MS m/z 328.7 (M++1).
85%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 90℃; for 18h; Inert atmosphere;	Preparation of 4-chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline To a degassed solution of 2,4-dichloro-7-methoxyquinoline (1 g, 4.3 mmol) in dioxane/water (8:2) was added 4-isopropoxyphenylboronic acid (870 mg, 4.82 mmol) followed by potassium carbonate (1.2 g, 8.7 mmol) and Pd(PPh3)4(253 mg, 0.22 mmol) at room temperature under nitrogen atmosphere. The reaction mass was heated at 90° C. for 18 h. The solvent was removed under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to afford 4-chloro-2-(4-isopropoxyphenyl)-7-methoxyquinoline (1.2 g, 85%) as off white solid. MS: MS m/z 328.7 (M++1)

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; BIOCON LIMITED - US2013/115190, 2013, A1 Location in patent: Page/Page column
[2]Current Patent Assignee: BIOCON LIMITED; BRISTOL-MYERS SQUIBB CO - US9527885, 2016, B2 Location in patent: Page/Page column 548

11
[ 1384973-12-9 ]
[ 153624-46-5 ]
[ 1558038-63-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 130℃; for 3h;Microwave irradiation;	A vial is charged with I-70 (0.50 g, 2.67 mmol), 4-isopropoxyboronic acid (0.58 g, 3.21 mmol), tetrakis(triphenylphosphine) palladium (0) (0.43 g, 0.37 mmol) and dissolved in aqueous potassium carbonate (4 mL, 2.0 M) and DME (3 mL). The mixture is heated at 130 C. for 3 h in a microwave. The mixture is filtered then diluted with water, extracted with EtOAc, dried over sodium sulphate, filtered, and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, 0-80% EtOAc in heptanes) to give I-77 (0.473 g, 73%) m/z 243.5 [M+H].

Reference： [1]Patent: US2014/45813,2014,A1 .Location in patent: Paragraph 0227

12
[ 153624-46-5 ]
[ 1124-29-4 ]
[ 1590402-40-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; pyridine N-oxide; oxygen; copper diacetate; In dichloromethane; at 20℃;Molecular sieve;	General procedure: [0561] To a solution of III-3 (1 eq.) in DCM (0.1 mmol/mL) was added boronic acid III-4 (2 eq.), Cu(OAc)2 (1 eq), Pyridine (10 eq.) and Pyridine-N-Oxide (2 eq.), followed by addition of 4 molecular sieve (quantity approx. equal to III-3). The reaction mixture was stirred at rt under oxygen atmosphere overnight. After completion of the reaction indicated by TLC, the resulting mixture was filtered and washed with, the filtrate was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel to give III-5. [0562] Compound 10 (61% yield): 1H NMR (DMSO-d6, 400 MHz) delta 8.43 (d, J=2.4 Hz, 1H), 7.90 (dd, J=9.6, 2.4 Hz, 1H), 7.39 (d, J=8.8 Hz, 2H), 7.06 (d, J=8.8 Hz, 2H), 6.51 (d, J=9.6 Hz, 1H), 3.81 (s, 3H), 2.41 (s, 3H).
	With pyridine; pyridine N-oxide; copper diacetate; In dichloromethane; at 20℃;Molecular sieve;	General procedure: To a solution of 111-3 (1 eq.) in DCM (0.1 mmol/mL) was added boronic acid III-4 (2 eq.), Cu(OAc)2 (1 eq), Pyridine (10 eq.) and Pyridine-N-Oxide (2 eq.), followed by addition of4A molecular sieve (quantity approx. equal to 111-3 ). The reaction mixture was stirred at rt underoxygen atmosphere overnight. After completion of the reaction indicated by TLC, the resultingmixture was filtered and washed with , the filtrate was washed with brine, dried over Na2SO4 andconcentrated. The residue was purified by column chromatography on silica gel to give 111-5.[0316] Compound 10 (61% yield): ?H NMR (DMSO-d6, 400 MHz) (5 8.43 (d, J = 2.4 Hz, 1H), 7.90 (dd, J= 9.6, 2.4 Hz, 1H), 7.39 (d, J= 8.8 Hz, 2H), 7.06 (d, J= 8.8 Hz, 2H), 6.51 (d, J = 9.6 Hz, 1H), 3.81 (s, 3H), 2.41 (s, 3H).

Reference： [1]Patent: US2014/94456,2014,A1 .Location in patent: Paragraph 0558; 0561-0562
[2]Patent: WO2015/153683,2015,A1 .Location in patent: Paragraph 0315; 0316

13
[ 24386-93-4 ]
[ 153624-46-5 ]
4-amino-5-(4-isopropoxyphenyl)-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 8268 - 8279

14
[ 13484-50-9 ]
[ 153624-46-5 ]
2,3,5,6-tetrakis(4-isopropoxyphenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 18h; Schlenk technique; Inert atmosphere;	6. General procedures and experimental data 6.1. Synthesis of tetraarylpyrazines General procedure: Prior to all, solutions of Pd(OAc)2 and P(Cy)3 were prepared in dried and argon filled Schlenk tubes (both 0.0125 mmol, 5 mol %) using 1 mL of extra dry THF and toluene, respectively. Solutions were stirred at room temperature for 10 min. To an argon-flushed glass pressure tube 50 mL of Pd(OAc)2 solution (0.000625 mmol, 0.25 mol %) was added (In cases of compounds 3k-p, 2 mol % (1.1 mg) of Pd(OAc)2 and 4 mol % (2.8 mg) of P(Cy)3 were used). After the removal of THF via evacuation of pressure tube, 100 mL of earlier prepared solution of P(Cy)3 (0.00125 mmol, 0.5 mol %), 2 (54 mg, 0.25 mmol), the appropriate arylboronic acid (2 mmol, 8.0 equiv) and K3PO4 (2 mmol, 8.0 equiv) were added, followed by the injection of dry toluene (3.5 mL). The tube was closed with a Teflon screw cap and the reaction mixture was stirred at 100 C for 18 h. Subsequently, the mixture was cooled down to room temperature and diluted with water and dichloromethane. The aqueous layer was extracted three times with dichloromethane. Combined organic layers were dried over Na2SO4 and filtered. Unless otherwise noted, solvent was evaporated and the residue was purified by column chromatography on silica gel using mixture of hexane and dichloromethane as eluent.

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Reimann, Sebastian; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Spannenberg, Anke; Lochbrunner, Stefan; Langer, Peter [Tetrahedron, 2015, vol. 71, # 38, p. 6803 - 6812]

15
[ 1146615-52-2 ]
[ 153624-46-5 ]
3-bromo-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 90℃; for 15h; Microwave irradiation;	C30.1 Step 1: 3-bromo-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine 3-bromo-6-iodoimidazo[1,2-a]pyridine (100 mg, 0.3 mmol) was added to a microwave reactor vial followed by 4-isopropoxyphenyl boronic acid (62 mg, 0.34 mmol), tetrakis(triphenylphosphine) palladium(0) (34 mg,0.03 mmol), sodium carbonate (94 mg, 0.9 mmol), 3 mL of 1,4-dioxane, and 1 mL of water. The mixture was capped tightly and degassed by bubbling nitrogen through the septum for 5 minutes. The resulting solution was heated to 90oC for 15 minutes in a microwave reactor and allowed to cool. The mixture was then diluted with ethyl acetate, washed with water (2x) and brine (1x), dried over sodium sulfate, and evaporated. The crude oil was purified by flash chromatography on silica (1:1 hexanes:ethyl acetate, isocratic) to provide the title compound (82 mg) as a light yellow oil that slowly solidified. LC/MS m/z: 331.24 (79Br, M+H)+, 333.28(81Br, M+H)+.
83%	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 90℃; for 15h; Microwave irradiation;	C30.1 Step 1: 3-bromo-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine 3-bromo-6-iodoimidazo[1,2-a]pyridine (100 mg, 0.3 mmol) was added to a microwave reactor vial followed by 4-isopropoxyphenyl boronic acid (62 mg, 0.34 mmol), tetrakis(triphenylphosphine) palladium(0) (34 mg,0.03 mmol), sodium carbonate (94 mg, 0.9 mmol), 3 mL of 1,4-dioxane, and 1 mL of water. The mixture was capped tightly and degassed by bubbling nitrogen through the septum for 5 minutes. The resulting solution was heated to 90oC for 15 minutes in a microwave reactor and allowed to cool. The mixture was then diluted with ethyl acetate, washed with water (2x) and brine (1x), dried over sodium sulfate, and evaporated. The crude oil was purified by flash chromatography on silica (1:1 hexanes:ethyl acetate, isocratic) to provide the title compound (82 mg) as a light yellow oil that slowly solidified. LC/MS m/z: 331.24 (79Br, M+H)+, 333.28(81Br, M+H)+.
80%	With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 90℃; for 5h; Inert atmosphere;	3-bromo-6-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine (2b) 3-bromo-6-iodoimidazo[1,2-a]pyridine (100 mg, 0.3 mmol) was addedto a microwave reactor vial followed by 4-isopropoxyphenyl boronic acid (62 mg,0.34 mmol), tetrakis(triphenylphosphine) palladium(0) (34 mg,0.03 mmol), sodiumcarbonate (94 mg, 0.9 mmol), 3 mL of 1,4-dioxane, and 1 mL of water. Themixture was capped tightly and degassed by bubbling nitrogen through the septumfor 5 minutes. The resulting solution was heated to 90 oC for 15minutes in a microwave reactor and allowed to cool. The mixture was thendiluted with ethyl acetate, washed with water (2x) and brine (1x), dried oversodium sulfate, and evaporated. The crude oil was purified by flash chromatographyon silica (1:1 hexanes:ethyl acetate, isocratic) to provide 82 mg (80%) of thetitle compound as a light yellow oil that slowly solidified. LC/MS m/z: calculated for C16H15BrN2O[79Br, M+H]+ 331.04, found 331.24; calculated for C16H15BrN2O[81Br, M+H]+ 333.04, found 333.28.

82 mg

With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 90℃; for 0.25h; Inert atmosphere; Microwave irradiation;

C30.1 Step 1: 3-bromo-6-[4-(propan-2-yloxy) phenyl]imidazo[1 ,2-a]pyridine 3-bromo-6-iodoimidazo[1 ,2-a]pyridine (100 mg, 0.3 mmol) was added to a microwave reactor vial followed by 4-isopropoxyphenyl boronic acid (62 mg, 0.34 mmol), tetrakis(triphenylphosphine) palladium(0) (34 mg,0.03 mmol), sodium carbonate (94 mg, 0.9 mmol), 3 mL of 1 ,4-dioxane, and 1 mL of water. The mixture was capped tightly and degassed by bubbling nitrogen through the septum for 5 minutes. The resulting solution was heated to 90 °C for 15 minutes in a microwave reactor andallowed to cool. The mixture was then diluted with ethyl acetate, washed with water (2x) and brine(lx), dried over sodium sulfate, and evaporated. The crude oil was purified by flash chromatography on silica (1:1 hexanes:ethyl acetate, isocratic) to provide the title compound (82 mg) as a light yellow oil that slowly solidified. LCMS m/z: 331.24 (79Br, M+H), 333.28(81Br, M+H).

Reference： [1]Current Patent Assignee: ARISAN THERAPEUTICS - WO2022/108849, 2022, A1 Location in patent: Page/Page column 76
[2]Current Patent Assignee: ARISAN THERAPEUTICS - WO2022/108849, 2022, A1 Location in patent: Page/Page column 76
[3]Plewe, Michael B.; Gantla, Vidyasagar Reddy; Sokolova, Nadezda V.; Shin, Young-Jun; Naik, Shibani; Brown, Eric R.; Fetsko, Alexandra; Zhang, Lihong; Kalveram, Birte; Freiberg, Alexander N.; Henkel, Greg; McCormack, Ken [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 41]
[4]Current Patent Assignee: ARISAN THERAPEUTICS - WO2018/13430, 2018, A2 Location in patent: Page/Page column 100; 101

16
[ 153624-46-5 ]
[ 459133-68-7 ]
3,5-bis[4-(propan-2-yloxy)phenyl]-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%		To a solution of <strong>[459133-68-7]tert-butyl 5-bromo-3-iodo-1H-indazole-1-carboxylate</strong> (30 mg, 0.O7lmmol) in dioxane (0.5 mL) were added (4-isopropoxyphenyl)boronic acid (25 mg, 0.l4mmol), [1,1?- bis(diphenylphosphino) ferrocene]dichloropalladium(ll) complex with dichloromethane (5.8 mg, 0.0071mmol), potassium carbonate (30 mg, 0.22mmol) and water (0.125 mL). The resulting reaction mixture was degassed with nitrogen for 10 mm, heated to 100C for 10 mm in a microwave reactor, then heated to 120C for additionall5 min.Then, the reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was dissolved in DCM (1 mL) and TFA (0.25 mL) was added dropwise. The reactionmixture was stirred at r.t. for 3 h, thenconcentratedinvacuo. The residue was purified by preparative HPLC to afford 7 mg (26%) of the product as a yellow solid.LC/MS m/z: 387.28 (M+H), 773.52 (2M+H).

Reference： [1]Patent: WO2018/13430,2018,A2 .Location in patent: Page/Page column 113

17
[ 474706-74-6 ]
[ 153624-46-5 ]
3,6-bis[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 12h;Inert atmosphere;	To a solution of 6-bromo-3-iodoimidazo[1 ,2-a]pyridine (0.3 g, 0.93 mmol) in dioxane (9 mL) and water (3 mL) was added (4-isopropoxyphenyl)boronic acid (0.334 g, 1 .86 mmol) and sodium carbonate (0.6g, 5.6 mmol). The reaction mixture was purged with nitrogen, then Pd(dppt)C12 (0.05 g, 0.06 mmol) was added. The resulting reaction mixture was heated to 90C for 12h, brought to room temperature and was extracted with ethyl acetate. Dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by SiC2 column chromatography (hexanes I EtOAc from 4:1 to 1:2) to give 0.24g (62%) of the title compound as a beige solid.1H NMR (300 MHz, CDCI3) O 8.37 (5, 1H), 7.70 (d, 1H),7.64 (5, 1 H), 7.49 (d, 2H), 7.44 (d, 2H), 7.41 (d, 1 H), 7.05 (d, 2H), 6.97 (d, 2H), 4.56 - 4.67 (m, 2H),1.40 (d, 6H), 1.37 (d, 6H).,LCIMS m/z: 387.28 (M+H).

Reference： [1]Patent: WO2018/13430,2018,A2 .Location in patent: Page/Page column 91

18
[ 474706-74-6 ]
[ 153624-46-5 ]
6-bromo-3-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 5h;Inert atmosphere;	To a solution of 6-bromo-3-iodoimidazo[1 ,2-a]pyridine (0.3 g, 0.93 mmol) in dioxane (9 mL) wereadded (4-isopropoxyphenyl)boronic acid (O.167g, 0.93mmol), tetrakis(triphenylphosphine)palladium(0) (0.075g, 0.065 mmol), sodium carbonate (0.3 g, 2.8 mmol) and water (3 mL). The resulting reaction mixture was degassed with nitrogen for 10 mm, then heated to 90C for 5 h. Then the reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over Na2504, filtered, and concentrated in vacuo. The residue was purified by SiC2 columnchromatography (hexanes I EtOAc from 4:1 to 1:2) to give 0.26g (84%) of the product as a white solid.1H NMR (500 MHz, CDCI3) O 8.36 (5, 1H), 7.62 (5, 1H), 7.57 (d, 1H), 7.42 (d, 2H), 7.23 (d, 1H), 7.03 (d, 2H), 4.62 (sep, 1H), 1.39 (d, 6H). LCIMS m/z: 331.07 (79Br, M+H), 333.14 (81Br, M+H).

Reference： [1]Patent: WO2018/13430,2018,A2 .Location in patent: Page/Page column 90

19
[ 474706-74-6 ]
[ 153624-46-5 ]
2-(4-{3-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridin-6-yl}phenyl)propan-2-ol [ No CAS ]

Reference： [1]Patent: WO2018/13430,2018,A2

20
[ 100-44-7 ]
[ 153624-46-5 ]
[ 35672-53-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	With 2-methoxy-10-(4-methoxyphenyl)-10H-phenothiazine; potassium carbonate In acetonitrile at 110℃; for 48h; Glovebox; chemoselective reaction;

Reference： [1]He, Zhiqi; Song, Feifei; Sun, Huan; Huang, Yong [Journal of the American Chemical Society, 2018, vol. 140, # 7, p. 2693 - 2699]

21
[ 131359-24-5 ]
[ 153624-46-5 ]
C₂₆H₂₄O₃ [ No CAS ]
C₂₆H₂₄O₃ [ No CAS ]

Reference： [1]ACS Catalysis,2020,vol. 10,p. 2596 - 2602

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