[ CAS No. 886365-06-6 ]

Name: 886365-06-6|Methyl 5-bromo-4-methylpicolinate|96%
Brand: Ambeed
SKU: A126868
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Quality Control of [ 886365-06-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 886365-06-6 ]

Product Details of [ 886365-06-6 ]

CAS No. :	886365-06-6	MDL No. :	MFCD07375102
Formula :	C₈H₈BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WNUFTWCRMKYPKE-UHFFFAOYSA-N
M.W :	230.06	Pubchem ID :	56763836
Synonyms :

Calculated chemistry of [ 886365-06-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.18
TPSA :	39.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.14
Log Po/w (XLOGP3) :	2.09
Log Po/w (WLOGP) :	1.94
Log Po/w (MLOGP) :	1.4
Log Po/w (SILICOS-IT) :	2.33
Consensus Log Po/w :	1.98

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.82
Solubility :	0.347 mg/ml ; 0.00151 mol/l
Class :	Soluble
Log S (Ali) :	-2.54
Solubility :	0.659 mg/ml ; 0.00286 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.35
Solubility :	0.103 mg/ml ; 0.000449 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 886365-06-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 886365-06-6 ]

* 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 [ 886365-06-6 ]
Downstream synthetic route of [ 886365-06-6 ]

[ 886365-06-6 ] Synthesis Path-Upstream 1~5

1
[ 886365-06-6 ]
[ 886365-02-2 ]

Reference： [1] Patent: WO2012/143329, 2012, A1, . Location in patent: Page/Page column 142-143

2
[ 67-56-1 ]
[ 886365-02-2 ]
[ 886365-06-6 ]

Yield	Reaction Conditions	Operation in experiment
49%	for 14 h; Reflux	To a solution of 5-Bromo-4-methyl-pyridine-2-carboxylic acid (650 mg, 3.0 mmol) in MeOH (2 ml) was added conc. H₂SO₄ (0.06 ml). The mixture was refluxed for 14 h, after which it was cooled to 0° C., neutralized with saturated NaHCO₃, filtered, concentrated, and purified by column chromatography to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (340 mg, 49percent) as white solid.
49%	for 14 h; Reflux	To a solution of 5-Bromo-4-methyl-pyridine-2-carboxylic acid (650 mg, 3.0 mmol) in MeOH (2 ml) was added conc. H₂SO₄ (0.06 ml). The mixture was refluxed for 14 h, after which it was cooled to 0° C., neutralized with saturated NaHCO₃, filtered, concentrated, and purified by column chromatography to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (340 mg, 49percent) as white solid.
49%	for 14 h; Reflux	To a solution of 5-Bromo-4-methyl-pyridine-2-carboxylic acid (650 mg, 3.0 mmol) in MeOH (2 ml) was added conc. H₂SO₄ (0.06 ml). The mixture was refluxed for 14 h, after which it was cooled to 0° C., neutralized with saturated NaHCO₃, filtered, concentrated, and purified by column chromatography to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (340 mg, 49percent) as white solid.

49%

for 14 h; Reflux

To a solution of 5-Bromo-4-methyl-pyridine-2-carboxylic acid (650 mg, 3.0 mmol) in MeOH (2 ml) was added conc. H₂SO₄ (0.06 ml).
The mixture was refluxed for 14 h, after which it was cooled to 0° C., neutralized with saturated NaHCO₃, filtered, concentrated, and purified by column chromatography to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (340 mg, 49percent) as white solid.

Reference： [1] Patent: US2011/71150, 2011, A1, . Location in patent: Page/Page column 34
[2] Patent: US2013/158040, 2013, A1, . Location in patent: Paragraph 0135
[3] Patent: US2013/158049, 2013, A1, . Location in patent: Paragraph 0169
[4] Patent: US2013/158066, 2013, A1, . Location in patent: Paragraph 0135

3
[ 3430-26-0 ]
[ 886365-06-6 ]

Reference： [1] Patent: US2011/71150, 2011, A1,
[2] Patent: US2013/158040, 2013, A1,
[3] Patent: US2013/158049, 2013, A1,
[4] Patent: US2013/158066, 2013, A1,

4
[ 67-56-1 ]
[ 1122090-38-3 ]
[ 886365-06-6 ]

Reference： [1] Patent: WO2012/143329, 2012, A1, . Location in patent: Page/Page column 142

5
[ 1122090-37-2 ]
[ 886365-06-6 ]

Reference： [1] Patent: US2011/71150, 2011, A1,
[2] Patent: WO2012/143329, 2012, A1,
[3] Patent: US2013/158040, 2013, A1,
[4] Patent: US2013/158049, 2013, A1,
[5] Patent: US2013/158066, 2013, A1,

[ 886365-06-6 ] Synthesis Path-Downstream 1~23

1
[ 1122090-37-2 ]
[ 886365-06-6 ]

Reference： [1]Patent: US2011/71150,2011,A1
[2]Patent: WO2012/143329,2012,A1
[3]Patent: US2013/158040,2013,A1

2
[ 886365-06-6 ]
[ 74-89-5 ]
[ 1279105-91-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With trimethylaluminum; at 100℃; for 1h;Sealed;	5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide: To <strong>[886365-06-6]5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester</strong> (200 mg, 0.869 mmol) and methylamine (135 mg, 11.34 mmol) was added (CH3)3Al (0.6 mg, 0.008 mmol). The mixture was placed in a sealed tube and heated at 100 C. for 1 h, after which the mixture was cooled, quenched with water, and extracted with EtOAc. The organic phase was dried, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide (130 mg, 65%) as an off-white solid.
65%	With trimethylaluminum; at 100℃; for 1h;Sealed tube;	5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide: To <strong>[886365-06-6]5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester</strong> (200 mg, 0.869 mmol) and methylamine (135 mg, 11.34 mmol) was added (CH3)3Al (0.6 mg, 0.008 mmol). The mixture was placed in a sealed tube and heated at 100 C. for 1 h, after which the mixture was cooled, quenched with water, and extracted with EtOAc. The organic phase was dried, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide (130 mg, 65%) as an off-white solid.
65%	With trimethylaluminum; at 100℃; for 1h;Sealed tube;	5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide: To <strong>[886365-06-6]5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester</strong> (200 mg, 0.869 mmol) and methylamine (135 mg, 11.34 mmol) was added (CH3)3Al (0.6 mg, 0.008 mmol). The mixture was placed in a sealed tube and heated at 100 C. for 1 h, after which the mixture was cooled, quenched with water, and extracted with EtOAc. The organic phase was dried, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide (130 mg, 65%) as an off-white solid.

65%

With trimethylaluminum; at 100℃; for 1h;Sealed tube;

To <strong>[886365-06-6]5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester</strong> (200 mg, 0.869 mmol) and methylamine (135 mg, 11.34 mmol) was added (CH3)3Al (0.6 mg, 0.008 mmol). The mixture was placed in a sealed tube and heated at 100 C. for 1 h, after which the mixture was cooled, quenched with water, and extracted with EtOAc. The organic phase was dried, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide (130 mg, 65%) as an off-white solid.

Reference： [1]Patent: US2011/71150,2011,A1 .Location in patent: Page/Page column 34
[2]Patent: US2013/158040,2013,A1 .Location in patent: Paragraph 0136
[3]Patent: US2013/158049,2013,A1 .Location in patent: Paragraph 0170
[4]Patent: US2013/158066,2013,A1 .Location in patent: Paragraph 0136

3
[ 3430-26-0 ]
[ 886365-06-6 ]

Reference： [1]Patent: US2011/71150,2011,A1
[2]Patent: US2013/158040,2013,A1
[3]Patent: US2013/158066,2013,A1

4
[ 67-56-1 ]
[ 886365-02-2 ]
[ 886365-06-6 ]

Yield	Reaction Conditions	Operation in experiment
49%	With sulfuric acid; for 14h;Reflux;	To a solution of 5-Bromo-4-methyl-pyridine-2-carboxylic acid (650 mg, 3.0 mmol) in MeOH (2 ml) was added conc. H2SO4 (0.06 ml).The mixture was refluxed for 14 h, after which it was cooled to 0° C., neutralized with saturated NaHCO3, filtered, concentrated, and purified by column chromatography to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (340 mg, 49percent) as white solid.
49%	With sulfuric acid; for 14h;Reflux;	To a solution of 5-Bromo-4-methyl-pyridine-2-carboxylic acid (650 mg, 3.0 mmol) in MeOH (2 ml) was added conc. H2SO4 (0.06 ml). The mixture was refluxed for 14 h, after which it was cooled to 0° C., neutralized with saturated NaHCO3, filtered, concentrated, and purified by column chromatography to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (340 mg, 49percent) as white solid.
49%	With sulfuric acid; for 14h;Reflux;	To a solution of 5-Bromo-4-methyl-pyridine-2-carboxylic acid (650 mg, 3.0 mmol) in MeOH (2 ml) was added conc. H2SO4 (0.06 ml). The mixture was refluxed for 14 h, after which it was cooled to 0° C., neutralized with saturated NaHCO3, filtered, concentrated, and purified by column chromatography to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (340 mg, 49percent) as white solid.

49%

With sulfuric acid; for 14h;Reflux;

To a solution of 5-Bromo-4-methyl-pyridine-2-carboxylic acid (650 mg, 3.0 mmol) in MeOH (2 ml) was added conc. H2SO4 (0.06 ml). The mixture was refluxed for 14 h, after which it was cooled to 0° C., neutralized with saturated NaHCO3, filtered, concentrated, and purified by column chromatography to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (340 mg, 49percent) as white solid.

Reference： [1]Patent: US2011/71150,2011,A1 .Location in patent: Page/Page column 34
[2]Patent: US2013/158040,2013,A1 .Location in patent: Paragraph 0135
[3]Patent: US2013/158049,2013,A1 .Location in patent: Paragraph 0169
[4]Patent: US2013/158066,2013,A1 .Location in patent: Paragraph 0135

5
[ 886365-06-6 ]
(2-fluoro-4-methoxyphenyl)boronic acid [ No CAS ]
[ 1374134-95-8 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In tetrahydrofuran; at 140℃; for 0.333333h;sealed tube; microwave irradiation;	(2-Fluoro-4-methoxyphenyl)boronic acid (177 mg, 1.043 mmol), methyl 5-bromo-4- methylpyridine-2-carboxylate (200 mg, 0.869 mmol), 1,3 bis(di-tert-butylphosphino)ferrocene palladium dichloride (89 mg, 0.130 mmol), cesium carbonate (623 mg, 1.913 mmol) and THF (5 mL) were sealed in a microwave vessel and subject to microwave irradiation at 140 C for 20 min. The reaction crude was combined with the crude from an identical probe reaction (44.3 mg scale). Volatiles were removed under reduced pressure. The resulting pot residue was purified by preparative HPLC (reverse phase, Kromasil 100-5C18, 100x21.1 mm) eluting with acetonitrile/water + 0.1% TFA (30% to 100% organic in 10 min, then to 100% for 2 min, 20 mL/min). Related fractions were pooled and evaporated under reduced pressure to afford a dark solid. This solid was further purified by flash chromatography (Si02, Biotage SNAP Cartridge, silica gel, KP-Sil, 50 g cartridge). The column was eluted with an EtOAc hexanes mixture (0% to 100%). Related fractions were pooled and evaporated to afford a light yellow oil as the titled compound. LCMS calc. = 275.10; found = 276.11 (M+H)+.

Reference： [1]Patent: WO2012/58187,2012,A1 .Location in patent: Page/Page column 94

6
[ 886365-06-6 ]
(2-fluoro-4-methoxyphenyl)boronic acid [ No CAS ]
[ 1374135-71-3 ]

Reference： [1]Patent: WO2012/58187,2012,A1

7
[ 67-56-1 ]
[ 1122090-38-3 ]
[ 886365-06-6 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; for 2h;Reflux;	Intermediate Example Int15.17.03methyl 5-bromo-4-methylpyridine-2-carboxylateTo a stirred suspension of the crude product Int15.17.02 (2.4 g) in methanol (90 mL) was added thionyl dichloride (2.01 mL). The mixture was heated to reflux for 2 h. The solvent was removed in vaccuum. A half-saturated solution of sodium bicarbonate was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum . Silicagel chromatography gave 1 .0 g of the title compound.

Reference： [1]Patent: WO2012/143329,2012,A1 .Location in patent: Page/Page column 142

8
[ 886365-06-6 ]
[ 886365-02-2 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate Example Int15.17.045-bromo-4-methylpyridine-2-carboxylic acid To a stirred solution of Int15.17.03 (1 .0 g) in THF (20 mL), methanol (5 mL) and water (5 mL) was added an aqueous solution of lithium hydroxide (6.1 mL; c = 1M). The mixture was stirred at r.t. for 1 h. Aqueous hydrochloric acid was added, until pH 4 was reached. The mixture was extracted with chloroform using a continous liquid /liquid extractor (from Normag Labor- und Prozesstechnik GmbH, llmenau, Germany) for 16 h. The solvent was removed in vacuum to give 870 mg of the title compound.

Reference： [1]Patent: WO2012/143329,2012,A1 .Location in patent: Page/Page column 142-143

9
[ 886365-06-6 ]
[ 5720-07-0 ]
[ 1432055-29-2 ]

Yield	Reaction Conditions	Operation in experiment
2.47 g	With 1,1'-bis(di-tert-butylphosphino)ferrocene palladium dichloride; potassium carbonate; In tetrahydrofuran; water; at 50 - 60℃; for 6h;Inert atmosphere;	Step 1 To a solution of <strong>[886365-06-6]5-bromo-4-methylpyridine-2-carboxylic acid methyl ester</strong> (2.207 g, 9.59 mmol), 4-methoxylphenylboronic acid (1.604 g, 10.55 mmol) and 1,1'-bis(di-tert-butylphosphino)ferrocene palladium dichloride (0.313 g, 0.480 mmol) in THF (30 mL) was added potassium carbonate (2.0 M in water, 10.1 mL, 20.15 mmol). The mixture was purged with nitrogen and heated at 50 C. for 1 hour and at 60 C. for 5 hours. The reaction was poured into ethyl acetate and was washed with brine, dried over sodium sulfate, filtered and concentrated. It was purified by column chromatography to yield methyl 5-(4-methoxyphenyl)-4-methylpyridine-2-carboxylate (2.47 g, 9.59 mmol) as a pink solid. MS ESI calc'd. for C15H16NO3 [M+H]+ 258.1. found 258.1.

Reference： [1]Patent: US2013/109649,2013,A1 .Location in patent: Paragraph 0256; 0257

10
[ 886365-06-6 ]
[ 1432055-31-6 ]

Reference： [1]Patent: US2013/109649,2013,A1

11
[ 886365-06-6 ]
[ 1432055-30-5 ]

Reference： [1]Patent: US2013/109649,2013,A1

12
[ 886365-06-6 ]
[ 141-43-5 ]
[ 1443684-69-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With trimethylaluminum; at 100℃; for 1h;Sealed tube;	5-Bromo-4-methyl-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide 5-Bromo-4-methyl-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide: To <strong>[886365-06-6]5-bromo-4-methyl-pyridine-2-carboxylic acid methyl ester</strong> (200 mg, 0.869 mmol) and 2-amino-ethanol (265 mg, 4.34 mmol) was added (CH3)3Al (0.6 mg, 0.008 mmol). The mixture was placed in a sealed tube and heated at 100 C. for 1 h, after which the mixture was cooled, quenched with water, and extracted with EtOAc. The organic phase was dried, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide (130 mg, 65%) as an off-white solid.
65%	With trimethylaluminum; at 100℃; for 1h;Sealed tube;	Intermediate 11: 5-Bromo-4-methyl-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide 5-Bromo-4-methyl-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide: To <strong>[886365-06-6]5-bromo-4-methyl-pyridine-2-carboxylic acid methyl ester</strong> (200 mg, 0.869 mmol) and 2-amino-ethanol (265 mg, 4.34 mmol) was added (CH3)3Al (0.6 mg, 0.008 mmol). The mixture was placed in a sealed tube and heated at 100 C. for 1 h, after which the mixture was cooled, quenched with water, and extracted with EtOAc. The organic phase was dried, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide (130 mg, 65%) as an off-white solid.
65%	With trimethylaluminum; at 100℃; for 1h;Sealed tube;	5-Bromo-4-methyl-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide 5-Bromo-4-methyl-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide: To <strong>[886365-06-6]5-bromo-4-methyl-pyridine-2-carboxylic acid methyl ester</strong> (200 mg, 0.869 mmol) and 2-amino-ethanol (265 mg, 4.34 mmol) was added (CH3)3Al (0.6 mg, 0.008 mmol). The mixture was placed in a sealed tube and heated at 100 C. for 1 h, after which the mixture was cooled, quenched with water, and extracted with EtOAc. The organic phase was dried, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide (130 mg, 65%) as an off-white solid.

Reference： [1]Patent: US2013/158040,2013,A1 .Location in patent: Paragraph 0138
[2]Patent: US2013/158049,2013,A1 .Location in patent: Paragraph 0171; 0172
[3]Patent: US2013/158066,2013,A1 .Location in patent: Paragraph 0138

13
[ 886365-06-6 ]
[ 1578253-28-7 ]
[ 1578253-27-6 ]

Yield	Reaction Conditions	Operation in experiment
26%	With copper(I) thiophene-2-carboxylate; caesium carbonate; In N,N-dimethyl-formamide; at 180℃; for 48h;Inert atmosphere; Sealed tube;	PREPARATION xl2: 5-(7-Fluoro-1-(tetrahydro-2H-pyran-2-yl)pyrazolo[4,3-b]indol-4(1H)-yl)-4-methylpicolinic acid [0188] 7-Fluoro-l-(tetrahydro-2H-pyran-2-yl)-l,4-dihydropyrazolo[4,3-]indole (200 mg, 0.771 mmol), <strong>[886365-06-6]methyl 5-bromo-4-methylpicolinate</strong> (302 mg, 1.311 mmol), ((thiophene-2- carbonyl)oxy)copper (14.71 mg, 0.077 mmol), CS2CO3 (754 mg, 2.314 mmol) and DMF (1.5 mL) were mixed in an 8 mL tube equipped with a magnetic stir bar to give a brown suspension. The solvent was purged with N2, and the tube was sealed and heated for 48 hours at 180C in a sand bath. The reaction mixture was subsequently partitioned between water (30 mL) and EtOAc (30 mL). The layers were separated. The organic layer was discarded and the aqueous layer was acidified with 6N HCl. The aqueous layer was extracted with EtOAc (2 x 30 mL). The combined organic layers were concentrated to yield a dark syrup, which was triturated with water (10 mL). A yellow solid was filtered off, washed with water (20 mL) and dried to give the title compound, which was used without further purification (80 mg, 26%).

Reference： [1]Patent: WO2014/39831,2014,A1 .Location in patent: Paragraph 0187-0188

14
[ 886365-06-6 ]
[ 1578255-48-7 ]

Reference： [1]Patent: WO2014/39831,2014,A1

15
[ 886365-06-6 ]
5-(7-fluoropyrazolo[4,3-b]indol-4(1H)-yl)-N-(1-(hydroxymethyl)cyclopropyl)-4-methylpicolinamide trifluoroacetate [ No CAS ]

Reference： [1]Patent: WO2014/39831,2014,A1

16
[ 886365-06-6 ]
5-(7-fluoropyrazolo[4,3-b]indol-4(1H)-yl)-N,4-dimethylpicolinamide trifluoroacetate [ No CAS ]

Reference： [1]Patent: WO2014/39831,2014,A1

17
[ 886365-06-6 ]
[ 126689-00-7 ]
C₁₂H₁₅NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 1h;Inert atmosphere; Microwave irradiation;	1-116: <strong>[886365-06-6]5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester</strong> (800 mg, 3.48 mmol) was dissolved in DMF (16 mL). Tetrakis(triphenylphosphine)palladium(0) (462 mg, 0.400 mmol), potassium carbonate (2.07 g, 15.0 mmol), and 2,2-dimethylethenylboronic acid pinacol ester (0.82 mL, 4.0 mmol) were added. Argon was bubbled through the mixture for 5 min. The mixture was heated to 120C in a microwave reactor for 1 h. The mixture was diluted with sat'd ammonium chloride (10 mL) then extracted with EtOAc (3x5 mL). The combined organics were dried over sodium sulfate and concentrated. The resulting crude material was purified by silica gel chromatagraphy using 0-40% EtOAc in heptanes as the gradient to provide compound 1-116.

Reference： [1]Patent: WO2017/4609,2017,A1 .Location in patent: Paragraph 0186

18
[ 886365-06-6 ]
C₁₂H₁₇NO₂ [ No CAS ]

Reference： [1]Patent: WO2017/4609,2017,A1

19
[ 886365-06-6 ]
[ 1122090-36-1 ]

Reference： [1]Patent: WO2017/4609,2017,A1

20
[ 886365-06-6 ]
(+/-)-trans-N-(8-amino-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methylpyrazol-4-yl)cyclopropanecarboxamide [ No CAS ]
[ 73183-34-3 ]
(+/-)-methyl 5-(1-amino-6-((trans)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamido)-2,7-naphthyridin-3-yl)-4-methylpicolinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
126 mg		Into a vial was weighed <strong>[886365-06-6]methyl 5-bromo-4-methylpicolinate</strong> (300 mg, 1.30 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (54.3 mg, 0.0652 mmol), bis(pinacolato)diboron (364 mg, 1.43 mmol), and potassium acetate (384 mg, 3.91 mmol). Under nitrogen, anhydrous 1,4-dioxane (6.5 mL) was added and the vial was sealed. The reaction mixture was stirred at 120 C. for 18 h. After cooling to rt, under nitrogen, to the reaction vessel was added (+-)-(trans)-N-(8-amino-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide (447 mg, 1.30 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (54.3 mg, 0.0652 mmol), and potassium carbonate (540 mg, 3.91 mmol), and water (1.3 mL). The vial was sealed and stirred at 100 C. for 23 h. The reaction mixture was concentrated to dryness and residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-85:15) to afford the target compound as a brown solid (126 mg, 21% over 2 steps); 1H NMR (400 MHz, DMSO-d6) delta 10.95 (s, 1H), 9.38 (s, 1H), 8.71 (s, 1H), 8.28 (s, 1H), 8.01 (s, 1H), 7.56 (s, 1H), 7.37 (br s, 2H), 7.29 (s, 1H), 7.05 (s, 1H), 3.91 (s, 3H), 3.77 (s, 3H), 2.25-2.16 (m, 2H), 1.90 (s, 3H), 1.43-1.34 (m, 1H), 1.24-1.14 (m, 1H).

Reference： [1]Patent: US2018/282328,2018,A1 .Location in patent: Paragraph 2267; 2268

21
[ 886365-06-6 ]
(+/-)-trans-N-(8-amino-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methylpyrazol-4-yl)cyclopropanecarboxamide [ No CAS ]
[ 73183-34-3 ]
(1S,2S)-N-(8-amino-6-(6-(methoxymethyl)-4-methylpyridin-3-yl)-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide [ No CAS ]
(1R,2R)-N-(8-amino-6-(6-(methoxymethyl)-4-methylpyridin-3-yl)-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29.6 mg		General procedure: Into a vial was weighed 1-(5-bromo-4-methylpyridin-2-yl)azetidin-2-one (50 mg, 0.207 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (8.6 mg, 0.0103 mmol), bis(pinacolato)diboron (52.7 mg, 0.207 mmol), and potassium acetate (61.1 mg, 0.622 mmol). Under nitrogen, anhydrous 1,4-dioxane (1.0 mL) was added and the vial was sealed. The reaction mixture was stirred at 100 C. for 17 h. After cooling to rt, under nitrogen, to the reaction vessel was added (+-)-(1S,2S)-N-(8-amino-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide (71.1 mg, 0.207 mmol), chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (8.8 mg, 0.0104 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (5.0 mg, 0.0104 mmol), potassium carbonate (86 mg, 0.622 mmol), and water (0.2 mL). The vial was sealed and stirred at 100 C. for 19 h. The reaction mixture was concentrated to dryness and residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-85:15) and then by HPLC to afford the target compound as a white solid (29.6 mg, 31% over 2 steps); 1H NMR (400 MHz, DMSO-d6) delta 10.92 (s, 1H), 9.35 (s, 1H), 8.34 (s, 1H), 8.24 (s, 1H), 7.56 (s, 1H), 7.52 (s, 1H), 7.29 (s, 1H), 7.28 (br s, 2H), 6.93 (s, 1H), 3.77 (s, 3H), 3.73 (dd, J=4.7, 4.7 Hz, 2H), 3.12 (dd, J=4.7, 4.7 Hz, 2H), 2.44 (s, 3H), 2.24-2.17 (m, 2H), 1.43-1.33 (m, 1H), 1.23-1.14 (m, 1H).

Reference： [1]Patent: US2018/282328,2018,A1 .Location in patent: Paragraph 2274; 2275; 2324; 2325

22
[ 886365-06-6 ]
(+/-)-(trans)-N-(8-(bis(2,4-dimethoxybenzyl)amino)-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide [ No CAS ]
[ 73183-34-3 ]
(+/-)-5-(1-bis(2,4-dimethoxybenzyl)amino)-6-((trans)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamido-2,7-naphthyridin-3-yl)-4-methylpicolinic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Into a vial was weighed <strong>[886365-06-6]methyl 5-bromo-4-methylpicolinate</strong> (1.00 g, 4.35 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (181 mg, 0.217 mmol), bis(pinacolato)diboron (1.21 g, 4.78 mmol), and potassium acetate (1.28 g, 13.0 mmol). Under nitrogen, anhydrous 1,4-dioxane (11 mL) was added and the vial was sealed. The reaction mixture was stirred at 100 C. for 18 h. After cooling to rt, the reaction mixture was concentrated and the residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-90:10) to afford 756 mg of crude aryl pinacolboranate intermediate (contaminated with pinacolborane by 1H NMR). Combining this intermediate (323 mg, ?1.17 mmol) with (+-)-(1S,2S)-N-(8-(bis(2,4-dimethoxybenzyl)amino)-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide (500 mg, 0.777 mmol), chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (32.8 mg, 0.0389 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (18.9 mg, 0.0389 mmol), and potassium phosphate tribasic monohydrate (554 mg, 2.33 mmol) in a vial, tetrahydrofuran (3.9 mL) and water (0.7 mL) were added under nitrogen and the vial was sealed and stirred at 80 C. for 19 h. The reaction mixture still contained starting material and so an equal aliquot of catalyst, ligand and water, as well as potassium phosphate tribasic monohydrate (184 mg, 0.777 mmol) and crude aryl pinacolboranate (215 mg, ?0.77 mmol) were added and stirred at 80 C. for 3 days. The mixture was concentrated to dryness and residue purified by flash column chromatography (CH2Cl2/MeOH, 100:0-90:10). The crude compound thus obtained was a yellow oil that contained the product according to HPLC-MS.

Reference： [1]Patent: US2018/282328,2018,A1 .Location in patent: Paragraph 2263; 2264

23
[ 886365-06-6 ]
(+/-)-(trans)-N-(8-(bis(2,4-dimethoxybenzyl)amino)-6-chloro-2,7-naphthyridin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamide [ No CAS ]
(+/-)-5-(1-amino-6-((trans)-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamido)-2,7-naphthyridin-3-yl)-N,N,4-trimethylpicolinamide [ No CAS ]

Reference： [1]Patent: US2018/282328,2018,A1

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P378
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H311	Toxic in contact with skin
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H316	Causes mild skin irritation
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H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 886365-06-6 ]

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[ 886365-06-6 ] Synthesis Path-Upstream 1~5

[ 886365-06-6 ] Synthesis Path-Downstream 1~23

Related Functional Groups of [ 886365-06-6 ]

Bromides

Esters

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Pyridines

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[ 886365-06-6 ]

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