[ CAS No. 1256810-26-0 ] {[proInfo.proName]}

Name: 1256810-26-0|6-Bromo-3-methoxypicolinic acid|95%
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SKU: A216593
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Quality Control of [ 1256810-26-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1256810-26-0 ]

CAS No. :	1256810-26-0	MDL No. :	MFCD11846420
Formula :	C₇H₆BrNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KRGGGVKGKFLABG-UHFFFAOYSA-N
M.W :	232.03	Pubchem ID :	71463965
Synonyms :

Calculated chemistry of [ 1256810-26-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.39
TPSA :	59.42 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) :	-6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.43
Log Po/w (XLOGP3) :	1.71
Log Po/w (WLOGP) :	1.55
Log Po/w (MLOGP) :	-0.6
Log Po/w (SILICOS-IT) :	1.41
Consensus Log Po/w :	1.1

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.59
Solubility :	0.591 mg/ml ; 0.00255 mol/l
Class :	Soluble
Log S (Ali) :	-2.57
Solubility :	0.62 mg/ml ; 0.00267 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.39
Solubility :	0.954 mg/ml ; 0.00411 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.01

Safety of [ 1256810-26-0 ]

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 [ 1256810-26-0 ]

* 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 [ 1256810-26-0 ]
Downstream synthetic route of [ 1256810-26-0 ]

[ 1256810-26-0 ] Synthesis Path-Upstream 1~6

1
[ 1256810-26-0 ]
[ 945954-95-0 ]

Reference： [1] Patent: WO2007/31558, 2007, A1, . Location in patent: Page/Page column 33

2
[ 945954-94-9 ]
[ 1256810-26-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With lithium hydroxide monohydrate; water In 1,4-dioxane at 25℃;	A mixture of methyl 6-bromo-3-methoxypicolinate (4 g, 18.4 mmol) and LiOH- H₂0 (1.6 g, 36.9 mmol) in dioxane / H₂0 (5 / 1, 40 mL) was stirred at RT overnight. After pH was adjusted to 7, the mixture was filtered to provide crude 6-bromo-3-methoxypicolinic acid (3.1 g, yield: 81 percent). 1H- MR (CDC1₃ , 400 MHz) δ 10.71 (m, 1H), 7.70 (d, J= 8.0 Hz, 1H), 7.40 (d, J= 8.0 Hz, 1H), 4.01 (s, 3H). MS (M+H)⁺: 232 / 234.

Reference： [1] Patent: WO2014/121418, 2014, A1, . Location in patent: Page/Page column 45
[2] Patent: WO2007/31558, 2007, A1, . Location in patent: Page/Page column 32
[3] Patent: WO2014/209727, 2014, A1, . Location in patent: Page/Page column 39-40
[4] Patent: WO2014/205593, 2014, A1, . Location in patent: Page/Page column 42

3
[ 945954-95-0 ]
[ 1256810-26-0 ]

Reference： [1] Patent: WO2013/134562, 2013, A1, . Location in patent: Paragraph 00325

4
[ 62733-99-7 ]
[ 1256810-26-0 ]

Reference： [1] Patent: WO2014/121418, 2014, A1,
[2] Patent: WO2014/209727, 2014, A1,
[3] Patent: WO2014/205593, 2014, A1,

5
[ 321601-48-3 ]
[ 1256810-26-0 ]

Reference： [1] Patent: WO2014/121418, 2014, A1,
[2] Patent: WO2014/209727, 2014, A1,
[3] Patent: WO2014/205593, 2014, A1,

6
[ 874-24-8 ]
[ 1256810-26-0 ]

Reference： [1] Patent: WO2014/121418, 2014, A1,

[ 1256810-26-0 ] Synthesis Path-Downstream 1~27

1
[ 945954-94-9 ]
[ 1256810-26-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With lithium hydroxide monohydrate; water; In 1,4-dioxane; at 25℃;	A mixture of methyl 6-bromo-3-methoxypicolinate (4 g, 18.4 mmol) and LiOH- H20 (1.6 g, 36.9 mmol) in dioxane / H20 (5 / 1, 40 mL) was stirred at RT overnight. After pH was adjusted to 7, the mixture was filtered to provide crude 6-bromo-3-methoxypicolinic acid (3.1 g, yield: 81 %). 1H- MR (CDC13 , 400 MHz) delta 10.71 (m, 1H), 7.70 (d, J= 8.0 Hz, 1H), 7.40 (d, J= 8.0 Hz, 1H), 4.01 (s, 3H). MS (M+H)+: 232 / 234.
	With sodium tetrahydroborate; In methanol; at 20℃; for 48h;	44 mmol of sodium borohydride are added in portions to a solution of 2.2 mmol of methyl 6- bromo-3-methoxypyridine-2-carboxylate in 750 ml of methanol. The mixture is stirred at room temperature for 2 days. Water is added to the reaction mixture, and it is extracted with dichloromethane (3x). The combined organic phases are dried with sodium sulphate and concentrated. The solid resulting after addition of n-hexane is filtered off with suction and dried.
	With lithium hydroxide monohydrate; In 1,4-dioxane; water; at 20℃;	A solution of methyl 6-bromo-3 -methoxypicolinate (3.0 g, 12.19 mmol) and LiOH-H20 (1.4 g, 33.36 mmol) in 1,4-dioxane / H20 (15 mL / 15 mL) was stirred at RT overnight. The mixture was filtered and the filtrate was adjusted to pH = 3 by aqueous HC1 (2 M) and extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2S04 and concentrated to give the crude product of 6-bromo-3-methoxypicolinic acid (2.1 g, yield: 73 %) without further purification. XH-NMR (CDC13, 400 MHz) delta 10.05 (br s, 1H), 7.70 (d, J = 8.8 Hz, 1H), 7.40 (d, J = 8.8 Hz, 1H), 4.01 (s, 3H). MS (M+H)+: 232 / 234.

With lithium hydroxide monohydrate; In 1,4-dioxane; water; at 25℃;

A solution of methyl 6-bromo-3-methoxypicolinate (3.0 g, 12.19 mmol) andLiOHH2O (1.4 g, 33.36 mmol) in 1,4-dioxane / H20 (15 mL / 15 mL) was stirred at RT overnight. The mixture was filtered and the filtrate was adjusted to pH = 3 by aqueous HC1 (2 M) and extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2504 andconcentrated to give the crude product of 6-bromo-3-methoxypicolinic acid (2.1 g, yield: 73 %)without further purification. ?H-NMR (CDC13, 400 MHz) 10.05 (br s, 1H), 7.70 (d, J = 8.8 Hz,1H), 7.40 (d, J = 8.8 Hz, 1H), 4.01 (s, 3H). MS (M+H): 232 / 234.

Reference： [1]Patent: WO2014/121418,2014,A1 .Location in patent: Page/Page column 45
[2]Patent: WO2007/31558,2007,A1 .Location in patent: Page/Page column 32
[3]Patent: WO2014/209727,2014,A1 .Location in patent: Page/Page column 39-40
[4]Patent: WO2014/205593,2014,A1 .Location in patent: Page/Page column 42

2
[ 1256810-26-0 ]
[ 945954-95-0 ]

Yield	Reaction Conditions	Operation in experiment
		3.3 mmol of oxalyl chloride are added to a solution of 1 ml of dimethyl sulphoxide in 10 ml of dichloromethane at -60C. The mixture is stirred at -60C until the evolution of gas subsides. A solution of the solid in 10 ml of dichloromethane is added dropwise at -60C. The reaction mixture is stirred at -30C for 30 minutes, again cooled to -60C, and 8.8 mmol of triethyl- amine are added. The mixture is stirred at room temperature for 30 minutes. Water and dichloromethane are added, the phases are separated, and the aqueous phase is extracted with dichloromethane (3x). It is evaporated, mixed with toluene, dried with sodium sulphate and evaporated. The crude title compound is identified by means of the Rf.

Reference： [1]Patent: WO2007/31558,2007,A1 .Location in patent: Page/Page column 33

3
[ 945954-95-0 ]
[ 1256810-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; at 20℃; for 16h;	To a solution of 6-bromo-3-methoxypicolinaldehyde (0.13 g, 0.60 mmol) in THF (6 mL) and tBuOH (6 mL) was added 2-methyl-2-butene (0.64 mL, 2.41 mmol), followed by an aqueous solution (2 mL) of sodium dihydrogen phosphate (0.29 mg, 2.4 mmol) and NaC102 (0.22 mg, 2.4 mol). The resulting mixture was stirred at RT for 16 hrs. The volatiles were then evaporated in vacuo and the residue thus obtained was purified on silica gel eluting with a solvent gradient of 0 to 10% MeOH in DCM (with 2% acetic acid as an additive in DCM) to afford 6-bromo-3-methoxypicolinic acid as a solid.

Reference： [1]Patent: WO2013/134562,2013,A1 .Location in patent: Paragraph 00325

4
[ 874-24-8 ]
[ 1256810-26-0 ]

Reference： [1]Patent: WO2014/121418,2014,A1

5
[ 62733-99-7 ]
[ 1256810-26-0 ]

Reference： [1]Patent: WO2014/121418,2014,A1
[2]Patent: WO2014/209727,2014,A1
[3]Patent: WO2014/205593,2014,A1

6
[ 321601-48-3 ]
[ 1256810-26-0 ]

Reference： [1]Patent: WO2014/121418,2014,A1
[2]Patent: WO2014/209727,2014,A1
[3]Patent: WO2014/205593,2014,A1

7
[ 1256810-26-0 ]
[ 1622052-62-3 ]
[ 1622052-63-4 ]

Reference： [1]Patent: WO2014/121418,2014,A1
[2]Patent: WO2014/121418,2014,A1

8
[ 1256810-26-0 ]
[ 1622053-07-9 ]

Reference： [1]Patent: WO2014/121418,2014,A1

9
[ 1256810-26-0 ]
[ 1622053-08-0 ]
[ 1622053-09-1 ]

Reference： [1]Patent: WO2014/121418,2014,A1
[2]Patent: WO2014/121418,2014,A1

10
[ 1256810-26-0 ]
[ 18645-88-0 ]
[ 1622053-07-9 ]
[ 1622053-06-8 ]

Yield	Reaction Conditions	Operation in experiment
37%; 14%	With polyphosphoric acid (PPA); at 120℃; for 14h;	A mixture of <strong>[1256810-26-0]6-bromo-3-methoxypicolinic acid</strong> (1.84 g, 7.93 mmol) and 3- fluorobenzene-l,2-diamine (1.0 g, 7.93 mmol) was stirred in PPA (3 mL) on a pre-heated oil- bath at 120 C for 14 h. The mixture was poured to ice-water and basified to pH = 8 with Na2C03. Then the mixture was filtrated to collect the brown solid as 6-bromo-2-(4-fluoro-lH- benzo[d]imidazol-2-yl)pyridin-3-ol (900 mg, yield: 37%). The filtrated was extracted with ethyl acetate, and the organic layer was washed with brine and dried over Na2S04. After concentrated, the residue was purified by column chromatography to give the product of 2-(6-bromo-3- methoxypyridin-2-yl)-4-fluoro-lH-benzo[d] imidazole (350 mg, yield: 14%). 1H- MR (CDC13, 400 MHz) delta 10.43-10.56 (m, 1H), 7.46 (d, J= 8.8 Hz, 1H), 7.33 (d, J= 8.8 Hz, 1H), 7.21-7.30 (m, 2H), 6.90-6.98 (m, 1H), 4.05 (s, 3H). MS (M+H) : 322 / 324.

Reference： [1]Patent: WO2014/121418,2014,A1 .Location in patent: Page/Page column 45; 46

11
[ 1256810-26-0 ]
6-bromo-N-(4-chlorobenzyl)-3-hydroxypicolinamide [ No CAS ]

Reference： [1]Patent: WO2014/209727,2014,A1
[2]Patent: WO2014/205593,2014,A1

12
[ 1256810-26-0 ]
6-bromo-3-(4-chlorobenzyl)-2H-pyrido[2,3-e][1,3]oxazin-4(3H)-one [ No CAS ]

Reference： [1]Patent: WO2014/209727,2014,A1
[2]Patent: WO2014/205593,2014,A1

13
[ 1256810-26-0 ]
5-(3-(4-chlorobenzyl)-4-oxo-3,4-dihydro-2H-pyrido[2,3-e][1,3]oxazin-6-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2014/209727,2014,A1
[2]Patent: WO2014/205593,2014,A1

14
[ 1256810-26-0 ]
[ 104-86-9 ]
6-bromo-N-(4-chlorobenzyl)-3-methoxypicolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 0℃; for 0.0833333h;	To a solution of (4-chlorophenyl)methanamine (610 mg, 4.31 mmol), 6-bromo-3- methoxypicolinic acid (1.0 g, 4.31 mmol) and triethylamine (1.31 g, 12.9 mmol) in DCM (10 mL) was added dropwise T3P (2.74 g, 8.61 mmol) at 0C. Five minutes later, TLC indicated the reaction was complete, and the mixture was suspended in water and extracted with DCM. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the crude 6-bromo-N-(4-chlorobenzyl)-3-methoxypicolinamide (1.3 g, yield: 87%) without further purification. -NMR (DMSO-i, 400 MHz) delta 8.98 (t, J = 6.0 Hz, 1H), 7.69 (d, J = 8.8 Hz, 1H), 7.58 (d, J = 8.8 Hz, 1H), 7.39-7.43 (m, 2H), 7.33 (d, J = 8.4 Hz, 2H), 4.22 (d, J = 6.4 Hz, 2H), 3.84 (s, 3H). MS (M+H)+: 355 / 357.
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 0℃; for 0.0833333h;	To a solution of(4-chlorophenyl)methanamine (610 mg, 4.31 mmol), <strong>[1256810-26-0]6-bromo-3-methoxypicolinic acid</strong> (1.0 g, 4.31 mmol) and triethylamine (1.31 g, 12.9 mmol) in DCM (10 mL)was added dropwise T3P (2.74 g, 8.61 mmol) at 0C. Five minutes later, TLC indicated the reaction was complete, and the mixture was suspended in water and extracted with DCM. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the crude 6-bromo-N-(4-chlorobenzyl)-3-methoxypicolinamide (1.3 g, yield: 87%) without further purification.?H-NMR (DM50-cl6, 400 MHz) 8.98 (t, J = 6.0 Hz, 1H), 7.69 (d, J = 8.8 Hz, 1H), 7.58 (d, J = 8.8Hz, 1H), 7.397.43 (m, 2H), 7.33 (d, J = 8.4 Hz, 2H), 4.22 (d, J = 6.4 Hz, 2H), 3.84 (s, 3H). MS(M+H): 355 / 357.

Reference： [1]Patent: WO2014/209727,2014,A1 .Location in patent: Page/Page column 40
[2]Patent: WO2014/205593,2014,A1 .Location in patent: Page/Page column 42

15
[ 1256810-26-0 ]
(1S,2S)-1-N-(6-fluoro-1,3-benzothiazol-2-yl)cyclopentane-1,2-diamine hydrochloride [ No CAS ]
6-bromo-N-[(1S,2S)-2-[(6-fluoro-1,3-benzothiazol-2-yl)amino]cyclopentyl]-3-methoxypyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU; In tetrahydrofuran; dichloromethane; at 20 - 25℃; for 72h;	To a solution of (IS, 2S)- 1 -A?-(6-fluoro- 1 ,3-benzothiazol -2-yl)cyclopentane- 1 ,2-di amine hydrochloride (Intermediate 1; 343 mg, 1.19 mmol) in dry DCM (4 ml) and THF (2 ml) was added <strong>[1256810-26-0]6-bromo-3-methoxypyridine-2-carboxylic acid</strong> (CAS number 1256810-26-0; (0506) 349 mg, 1.50 mmol), HATU (680 mg, 1 .79 mmol) and tri ethyl amine (498 mu, 3.58 mmol) The reaction mixture was stirred at room temperature for 72 hours then partitioned between DCM and a saturated solution of sodium bicarbonate. The organics were filtered through a hydrophobic frit and concentrated in vacuo. The caide material was purified by column chromatography (silica, 0 - 100 % ethyl acetate / petrol then 0 - 30 % methanol / ethyl acetate) and then further purified by column chromatography (silica, 0 - 100 % ethyl acetate / petrol then 0 - 30 % methanol / ethyl acetate) to afford the title compound. (0507) 1H NMR (DMSO-t) delta ppm 1.50-1.72 (m, 2 H), 1.69-1.78 (m, 2 H), 2,05-2, 18 (m, 2 H), 3.72 (s, 3 H), 4.14-4.25 (m, 2 H), 6.99-7.08 (m, 1 H), 7.29-7.34 (m, 1 H), 7.50-7.69 (m, 3 H), 8, 13-8,21 (m, 1 H), 8,54-8,62 (m, 1 H) (0508) MS ES+: 466 / 468

Reference： [1]Patent: WO2015/124934,2015,A1 .Location in patent: Page/Page column 48

16
[ 1256810-26-0 ]
[ 74-88-4 ]
[ 945954-94-9 ]