[ CAS No. 886365-02-2 ]

Name: 886365-02-2|5-Bromo-4-methylpyridine-2-carboxylic acid|98%
Brand: Ambeed
SKU: A164415
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Quality Control of [ 886365-02-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 886365-02-2 ]

Product Details of [ 886365-02-2 ]

CAS No. :	886365-02-2	MDL No. :	MFCD07375100
Formula :	C₇H₆BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RMSVDYVOLGRLNJ-UHFFFAOYSA-N
M.W :	216.03 g/mol	Pubchem ID :	45790031
Synonyms :

Calculated chemistry of [ 886365-02-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.86
TPSA :	50.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.36
Log Po/w (XLOGP3) :	1.77
Log Po/w (WLOGP) :	1.85
Log Po/w (MLOGP) :	-0.02
Log Po/w (SILICOS-IT) :	1.85
Consensus Log Po/w :	1.36

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.63
Solubility :	0.504 mg/ml ; 0.00233 mol/l
Class :	Soluble
Log S (Ali) :	-2.44
Solubility :	0.781 mg/ml ; 0.00361 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.65
Solubility :	0.489 mg/ml ; 0.00226 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.64

Safety of [ 886365-02-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 886365-02-2 ]

* 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 [ 886365-02-2 ]
Downstream synthetic route of [ 886365-02-2 ]

[ 886365-02-2 ] Synthesis Path-Upstream 1~6

1
[ 1122090-37-2 ]
[ 886365-02-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium permanganate In water; acetone at 20℃; for 72 h;	To a solution of 5-Bromo-4-methyl-2-vinyl-pyridine (600 mg, 3 mmol) in acetone-water (1:1, 54 ml) was added KMnO₄ (957 mg, 6 mmol). The mixture was stirred for 3 days at rt, at which point it was filtered, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid (700 mg, 92percent) as white solid.
92%	With potassium permanganate In water; acetone at 20℃; for 72 h;	To a solution of 5-Bromo-4-methyl-2-vinyl-pyridine (600 mg, 3 mmol) in acetone-water (1:1, 54 ml) was added KMnO₄ (957 mg, 6 mmol). The mixture was stirred for 3 days at rt, at which point it was filtered, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid (700 mg, 92percent) as white solid.
92%	With potassium permanganate In water; acetone at 20℃; for 72 h;	To a solution of 5-Bromo-4-methyl-2-vinyl-pyridine (600 mg, 3 mmol) in acetone-water (1:1, 54 ml) was added KMnO₄ (957 mg, 6 mmol). The mixture was stirred for 3 days at rt, at which point it was filtered, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid (700 mg, 92percent) as white solid.

92%

With potassium permanganate In water; acetone at 20℃; for 72 h;

To a solution of 5-Bromo-4-methyl-2-vinyl-pyridine (600 mg, 3 mmol) in acetone-water (1:1, 54 ml) was added KMnO₄ (957 mg, 6 mmol).
The mixture was stirred for 3 days at rt, at which point it was filtered, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid (700 mg, 92percent) as white solid.

Reference： [1] Patent: US2011/71150, 2011, A1, . Location in patent: Page/Page column 33-34
[2] Patent: US2013/158040, 2013, A1, . Location in patent: Paragraph 0134
[3] Patent: US2013/158049, 2013, A1, . Location in patent: Paragraph 0168
[4] Patent: US2013/158066, 2013, A1, . Location in patent: Paragraph 0134
[5] Patent: WO2012/143329, 2012, A1,

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

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

3
[ 3430-26-0 ]
[ 124-38-9 ]
[ 886365-02-2 ]

Reference： [1] Patent: WO2016/109221, 2016, A1, . Location in patent: Page/Page column 129

4
[ 3430-26-0 ]
[ 886365-02-2 ]

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,

5
[ 1122090-38-3 ]
[ 886365-02-2 ]

Reference： [1] Patent: WO2012/143329, 2012, A1,

6
[ 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

[ 886365-02-2 ] Synthesis Path-Downstream 1~21

1
[ 1122090-37-2 ]
[ 886365-02-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium permanganate; In water; acetone; at 20℃; for 72h;	To a solution of 5-Bromo-4-methyl-2-vinyl-pyridine (600 mg, 3 mmol) in acetone-water (1:1, 54 ml) was added KMnO4 (957 mg, 6 mmol).The mixture was stirred for 3 days at rt, at which point it was filtered, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid (700 mg, 92percent) as white solid.
92%	With potassium permanganate; In water; acetone; at 20℃; for 72h;	To a solution of 5-Bromo-4-methyl-2-vinyl-pyridine (600 mg, 3 mmol) in acetone-water (1:1, 54 ml) was added KMnO4 (957 mg, 6 mmol). The mixture was stirred for 3 days at rt, at which point it was filtered, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid (700 mg, 92percent) as white solid.
92%	With potassium permanganate; In water; acetone; at 20℃; for 72h;	To a solution of 5-Bromo-4-methyl-2-vinyl-pyridine (600 mg, 3 mmol) in acetone-water (1:1, 54 ml) was added KMnO4 (957 mg, 6 mmol). The mixture was stirred for 3 days at rt, at which point it was filtered, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid (700 mg, 92percent) as white solid.

92%

With potassium permanganate; In water; acetone; at 20℃; for 72h;

To a solution of 5-Bromo-4-methyl-2-vinyl-pyridine (600 mg, 3 mmol) in acetone-water (1:1, 54 ml) was added KMnO4 (957 mg, 6 mmol). The mixture was stirred for 3 days at rt, at which point it was filtered, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid (700 mg, 92percent) as white solid.

Reference： [1]Patent: US2011/71150,2011,A1 .Location in patent: Page/Page column 33-34
[2]Patent: US2013/158040,2013,A1 .Location in patent: Paragraph 0134
[3]Patent: US2013/158049,2013,A1 .Location in patent: Paragraph 0168
[4]Patent: US2013/158066,2013,A1 .Location in patent: Paragraph 0134
[5]Patent: WO2012/143329,2012,A1

2
[ 3430-26-0 ]
[ 886365-02-2 ]

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

3
[ 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

4
[ 886365-02-2 ]
[ 1279105-91-7 ]

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

5
[ 1122090-38-3 ]
[ 886365-02-2 ]

Reference： [1]Patent: WO2012/143329,2012,A1

6
[ 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

7
[ 886365-02-2 ]
[ 1443684-69-2 ]

Reference： [1]Patent: US2013/158040,2013,A1

8
[ 886365-02-2 ]
[ 2561-17-3 ]
C₁₅H₁₀FNO₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 7976 - 7996

9
[ 886365-02-2 ]
[ 2561-17-3 ]
(R)-6-((3-fluorophenyl)ethynyl)-N-(3-hydroxy-3-methylbutan-2-yl)-5-methylnicotinamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 7976 - 7996

10
[ 886365-02-2 ]
C₇H₈BrNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With borane-THF; In tetrahydrofuran; at 0 - 23℃;	Step 1: [0420] To a solution of <strong>[886365-02-2]5-bromo-4-methylpicolinic acid</strong> (400 mg, 1.85 mmol) in dry THF (3 mL) was added borane THF complex (1M in THF, 7.4 mL, 7.4 mmol) at 0° C. and the mixture was stirred at RT overnight. The mixture was cooled to 0° C. and aqueous NH4Cl was added. The mixture was extracted with EtOAc, the combined organic layers were dried and the volatiles were removed under reduced pressure (308 mg, 82percent).

Reference： [1]Patent: US2015/166505,2015,A1 .Location in patent: Paragraph 0418; 0419; 0420

11
[ 886365-02-2 ]
5-bromo-2-(methoxymethyl)-4-methylpyridine [ No CAS ]

Reference： [1]Patent: US2015/166505,2015,A1

12
[ 886365-02-2 ]
5-bromo-4-methylpicolinoyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With thionyl chloride; at 90℃; for 2h;	5-Bromo-4-methylpicolinoyl chloride (B19.1) (0412) A mixture of <strong>[886365-02-2]5-bromo-4-methylpicolinic acid</strong> (5.6 mmol, 1.2 g) and 10 mL thionyl chloride was stirred at 90° C. for 2 h. After cooling to the rt, the mixture was concentrated to give the title compound (1 g, 77percent) as a yellow solid. LC-MS: [M+H]+=236.1.
77%	With thionyl chloride; at 90℃; for 2h;	A mixture of 5-bromo-4- methylpicolinic acid (5.6 mmol, 1 .2g) and 10 mL thionyl chloride was stirred at 90 °C for2 h. After cooling to the rt, the mixture was concentrated to give the title compound (ig,77percent) as a yellow solid. LC-MS: [M+H] = 236.1.
	With thionyl chloride; at 90℃; for 1.5h;	Intermediate 43. Step 2; 5-bromo-4-methyl-N-(4-(trifluoromethyl) pyridin-2-yl) picolinamide <strong>[886365-02-2]5-bromo-4-methylpicolinic acid</strong> (600 mg, 2.78 mmol) and SOCI2 (10 mL, 137 mmol) were heated to reflux at 90 °C. Excess SOCI2 was removed by distillation after 1.5 hours. Anhydrous toluene (5 mL) was added to the residue, and then evaporated to remove remaining SOCI2 to give the corresponding acid chloride. To a solution of 4-(trifluoromethyl)pyridin-2-amine (540 mg, 3.33 mmol) and Et3N (1.161 mL, 8.33 mmol) in CH2CI2 (6 mL), the solution of acid chloride in anhydrous CH2CI2 (10 mL) was added over a period of 10 min at 0 °C. The reaction mixture was then stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using EtOAc to give 5-bromo-4-methyl-N-(4-(trifluoromethyl) pyridin-2-yl) picolinamide. 1HNMR (400 MHz, CDCI3): delta = 10.52 (s, 1 H), 8.66 (d, J= 14.8 Hz, 2 H), 8.51 (d, J= 4.4 Hz, 1 H), 8.13 (s, 1 H), 7.28 (d, J = 4.8 Hz, 1 H), 2.51 (s, 3 H). MS: 359.9 (M+l) ppm.

With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; at 0 - 20℃; for 42h;Inert atmosphere;

To a solution of <strong>[886365-02-2]5-bromo-4-methylpicolinic acid</strong> (2.00 g, 9.26 mmol) and anhydrous DMF (0.14 mL, 1.9 mmol) in anhydrous tetrahydrofuran (31 mL) under nitrogen and at 0° C., was added oxalyl chloride over 10 min (1.61 mL, 18.5 mmol). The ice bath was removed, allowing the mixture to come to rt. After 42 h, the mixture was concentrated to dryness. The crude acid chloride was then dissolved in anhydrous tetrahydrofuran (31 mL) and L-valinol (1.1 mL, 9.3 mmol) was added. The reaction mixture was stirred for 7 days and then poured into sat. aq. sodium bicarbonate and extracted with isopropyl acetate. The organics were washed with brine, dried over magnesium sulfate and then concentrated to dryness. The residue thus obtained was purified by flash column chromatography (heptane/iPrOAc, 100:0-0:100) to afford the title compound as a yellow liquid (1.08 g, 39percent); 1H NMR (400 MHz, DMSO-d6) delta 8.73 (s, 1H), 8.24 (br d, J=9.7 Hz, 1H), 8.03 (s, 1H), 4.73 (t, J=5.4 Hz, 1H), 3.78-3.70 (m, 1H), 3.63-3.54 (m, 1H), 3.54-3.44 (m, 1H), 2.46 (s, 3H), 1.96-1.87 (m, 1H), 0.91 (d, J=6.6 Hz, 3H), 0.86 (d, J=6.9 Hz, 3H).

Reference： [1]Patent: US2016/176882,2016,A1 .Location in patent: Paragraph 0411; 0412
[2]Patent: WO2017/221100,2017,A1 .Location in patent: Paragraph 00206
[3]Patent: WO2016/109221,2016,A1 .Location in patent: Page/Page column 129-130
[4]Patent: US2018/282328,2018,A1 .Location in patent: Paragraph 2331; 2332

13
[ 886365-02-2 ]
(5-bromo-4-methylpyridin-2-yl)(pyrrolidin-1-yl)methanone [ No CAS ]

Reference： [1]Patent: US2016/176882,2016,A1

14
[ 886365-02-2 ]
5-bromo-N,N,4-trimethylpicolinamide [ No CAS ]

Reference： [1]Patent: US2016/176882,2016,A1
[2]Patent: WO2017/221100,2017,A1

15
[ 25519-82-8 ]
[ 886365-02-2 ]
2-(4-(4-methoxybenzoyl)piperidinylcarbonyl)-4-methyl-5-bromopyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;	Compound 7-105 was synthesized as follows: 2-(4-(4-methoxybenzoyl)piperidinylcarbonyl)-4-methyl-5-bromopyridine: To a mixture of 5-bromo-4-methylpyridine-2-carboxylic acid (0.400 g, 1.85 mmol, 1.0 eq) and <strong>[25519-82-8]4-(4-methoxybenzoyl)piperidine hydrochloride</strong> (0.474 g, 1.85 mmol, 1.0 eq) was added dimethylformamide (10 mL) followed by triethylamine (0.64 mL, 4.36 mmol, 2.5 eq). HATU (0.774 g, 2.04 mmol, 1.1 eq) was added forming a yellow solution, which was stirred at room temperature for 1 day. The reaction was partitioned between EtOAc (120 mL) and water-NaHCO3 (1:1, 120 mL). The organics were further washed with brine (120 mL), water (120 mL) and brine (100 mL), dried (Na2SO4) and concentrated under reduced pressure. MPLC (0?10percent MeOH-CH2Cl2) yielded the title compound (0.693 g, 89percent) as a yellow oil; 1H nmr (CDCl3) delta 8.55 (1H, s, pyH-3 or H-6), 7.90 (2H, d, J 9.0 Hz, 2H of C6H4OMe), 7.48 (1H, s, pyH-3 or H-6), 6.91 (2H, d, J 9.0 Hz, 2H of C6H4OMe), 4.64 (1H, m, 1H of BzpipH-2, H-6), 4.01 (1H, m, 1H of BzpipH-2, H-6), 3.83 (3H, s, OCH3), 3.49 (1H, m, BzpipH-4), 3.23 (1H, m, 1H of BzpipH-2, H-6), 3.03 (1H, m, 1H of BzpipH-2, H-6), 2.39 (3H, s, pyCH3), 1.95 (1H, m, 1H of BzpipH-3, H-5), 1.86-1.75 (3H, s, 3H of BzpipH-3, H-5); m/z 417, 419 [M+H]+.

Reference： [1]Patent: US9409884,2016,B2

16
[ 3430-26-0 ]
[ 124-38-9 ]
[ 886365-02-2 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 43. Step 1; 5-bromo-4-methylpicolinic acid To a solution of 2,5-dibromo-4-methylpyridine (3 g, 11.96 mmol) in anhydrous toluene (40 ml)) was added BuLi (5.74 ml, 14.35 mmol) at -78 °C dropwise. The reaction mixture was stirred at - 78 °C for 1 h. Then the reaction mixture was poured into a 100 mL beaker with dry carbon dioxide (4 g, 91 mmol). The reaction mixture was stirred at 20 °C for another 10 minutes. Then the mixture was poured into saturated citric acid and a yellow precipitate was formed. The suspension was filtered and the solid was collected, dried in vacuo to give 5-bromo-4- methylpicolinic acid. 1HNMR (400 MHz, DMSO-i): delta = 8.71 (s, 1 H), 7.99 (s, 1 H), 2.40 (s, 3 H). MS: 215.9 (M+l) ppm.

Reference： [1]Patent: WO2016/109221,2016,A1 .Location in patent: Page/Page column 129

17
[ 886365-02-2 ]
5-bromo-4-methyl-N-(4-(trifluoromethyl)pyridin-2-yl)picolinamide [ No CAS ]

Reference： [1]Patent: WO2016/109221,2016,A1

18
[ 886365-02-2 ]
4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)picolinamide [ No CAS ]

Reference： [1]Patent: WO2016/109221,2016,A1

19
[ 886365-02-2 ]
methyl (S)-2-(5-(1-amino-6-(trans-2-(1-methyl-1H-pyrazol-4-yl)cyclopropane-1-carboxamido)-2,7-naphthyridin-3-yl)-4-methylpyridin-2-yl)-4,5-dihydrooxazole-4-carboxylate [ No CAS ]

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

20
[ 886365-02-2 ]
(S)-5-bromo-N-(1-hydroxy-3-methylbutan-2-yl)-4-methylpicolinamide [ No CAS ]

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

21
[ 886365-02-2 ]
(S)-methyl 2-amino-3-hydroxypropanoate hydrochloride [ No CAS ]
methyl (5-bromo-4-methylpicolinoyl)-L-serinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%		To a solution of <strong>[886365-02-2]5-bromo-4-methylpicolinic acid</strong> (3.00 g, 13.9 mmol) in anhydrous tetrahydrofuran (46 mL) under nitrogen and at 0° C., was added anhydrous DMF (0.10 mL, 1.4 mmol) followed by dropwise addition of oxalyl chloride over 10 min (1.80 mL, 20.8 mmol). After 5 minutes of stirring, the ice bath was removed, allowing the mixture to come to rt. After 19 h, the mixture was concentrated to dryness. In a separate flask, a solution of L-serine methyl ester hydrochloride (2.38 g, 15.3 mmol) in anhydrous tetrahydrofuran (25 mL) was charged with triethylamine (2.3 mL, 17 mmol) and stirred for 1 h before being poured onto the dried acyl chloride prepared above. The combined reaction mixture was stirred for a further 1.5 h and then poured into sat. aq. sodium bicarbonate and extracted with isopropyl acetate. The organics were washed with brine, dried over magnesium sulfate and then concentrated to dryness. The residue thus obtained was purified by flash column chromatography (CH2Cl2/MeOH, 100:0-95:5) to afford the title compound as a yellow solid (1.457 g, 33percent); 1H NMR (400 MHz, Chloroform-d) delta 8.69 (br d, J=7.9 Hz, 1H), 8.60 (s, 1H), 8.04 (s, 1H), 4.85 (dt, J=7.9, 3.9 Hz, 1H), 4.17-3.98 (m, 2H), 3.83 (s, 3H), 2.57 (t, J=6.1 Hz, 1H), 2.47 (s, 3H).

Reference： [1]Patent: US2018/282328,2018,A1 .Location in patent: Paragraph 2327; 2328

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[ CAS No. 886365-02-2 ]

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[ 886365-02-2 ] Synthesis Path-Upstream 1~6

[ 886365-02-2 ] Synthesis Path-Downstream 1~21

Related Functional Groups of [ 886365-02-2 ]

Bromides

Carboxylic Acids

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Pyridines

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[ 886365-02-2 ]

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[ 886365-02-2 ]