[ CAS No. 886365-47-5 ]

Name: 886365-47-5|1-(5-Bromo-2-chloropyridin-3-yl)ethanone|98%
Brand: Ambeed
SKU: A644929
Rating: 97 (25 reviews)

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Quality Control of [ 886365-47-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 886365-47-5 ]

SDS Specification

Alternatived Products of [ 886365-47-5 ]

Product Details of [ 886365-47-5 ]

CAS No. :	886365-47-5	MDL No. :	MFCD08436181
Formula :	C₇H₅BrClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SQKOULMBBLJIKX-UHFFFAOYSA-N
M.W :	234.48 g/mol	Pubchem ID :	25417865
Synonyms :

Calculated chemistry of [ 886365-47-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.14
TPSA :	29.96 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) :	-6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.92
Log Po/w (XLOGP3) :	2.19
Log Po/w (WLOGP) :	2.7
Log Po/w (MLOGP) :	1.47
Log Po/w (SILICOS-IT) :	2.97
Consensus Log Po/w :	2.25

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.01
Solubility :	0.229 mg/ml ; 0.000975 mol/l
Class :	Soluble
Log S (Ali) :	-2.45
Solubility :	0.826 mg/ml ; 0.00352 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.84
Solubility :	0.0342 mg/ml ; 0.000146 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.78

Safety of [ 886365-47-5 ]

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 [ 886365-47-5 ]

* 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 [ 886365-47-5 ]
Downstream synthetic route of [ 886365-47-5 ]

[ 886365-47-5 ] Synthesis Path-Upstream 1~5

1
[ 885223-63-2 ]
[ 886365-47-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With methylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 0.5 h; Inert atmosphere	To a solution of compound 12b (2.0 g, 7.15 mmol) in anhydrous THF (15mL) was added methylmagnesium bromide (1M in THF, 8 mL, 8 mmol) dropwise at 0 °C under Argon atmosphere. The resulting mixture was stirred at room temperature for 30 min. The reaction was quenched with sat. NH₄Cl solution, diluted with water (50 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over anhydrous Na₂SO₄, filtered and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 6:1, v/v) to give the title compound 12c (1.5 g, 90percent yield) as a yellow solid.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 790 - 793

2
[ 1111638-41-5 ]
[ 886365-47-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With pyridine; chromium(VI) oxide In dichloromethane at 0 - 20℃; Silica gel	Preparation of 1-(5-bromo-2-chloropyridin-3-yl)ethanone (D-2-5). <n="106"/>To a stirred solution of pyridine (13 g, 0.165 mol) in CH₂CI₂ (200 mL) was added CrO₃ (8.25 g, 0.083 mol) and silica gel (20 mL) portionwise at 0 °C. After the addition, the reaction mixture was stirred for 10 minutes. Compound D-2-4 (6.5 g, 27.5 mmol) was then added and the resulting mixture was stirred at room temperature overnight. TLC (petroleum ether/EtOAc 8:1 ) indicated most of compound D-2-4 was consumed. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give crude compound D-2-5, which was purified by column chromatography (silica gel petroleum ether/EtOAc 20:1) to give pure compound D-2-5 (5 g, yield: 77percent) as a yellow oil.

Reference： [1] Patent: WO2009/16460, 2009, A2, . Location in patent: Page/Page column 104-105

3
[ 885223-63-2 ]
[ 75-16-1 ]
[ 886365-47-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	at 0 - 20℃; for 0.5 h; Inert atmosphere	To a solution of compound4(2.0 g, 7.15 mmol) in anhydrous THF (15mL) was addedmethylmagnesium bromide(1M in THF, 8 mL, 8 mmol) dropwise at 0°Cunderargon atmosphere. The resulting mixture was stirred at room temperaturefor 30 min. The reaction was quenched with sat. NH₄Cl solution,diluted withwater(50 mL) and extracted with ethyl acetate (50 mL×3).The combined organic layers werewashed with water (50 mL) and brine (50 mL), dried over anhydrous Na₂SO₄, filtered and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=6:1, v/v) to give the title compound5as a yellow solid(1.5 g, 90percent yield). ¹H NMR (400 MHz, DMSO-d₆) δ 8.71 (d,J= 2.5 Hz, 1H), 8.46 (d,J= 2.5 Hz, 1H), 2.62 (s, 3H).
54.3%	at -78℃; for 3 h;	Starting material 5-bromo-2- chloro-N-methoxy-N-methylnicotinamide (5.0 g, 17.89 mmol) was charged into a 250 ml round bottom flask and the flask was chilled to -78 ⁰C. Methyl magnesium bromide 96.5 ml, 19.68 mmol) in 5 ml THF was added dropwise via addition funnel. The resulting mixture was allowed to stir for 3 hours at -78 ⁰C. After removing the THF solvent via rotatory evaporation under reduced pressure, the reaction mixture was partitioned between ethylacetate and saturated aqueous sodium bicarbonate. After removing the ethylacetate, the resulting crude product was subject to a silica gel column with 20percent ethylacetate in hexane. The resulting product (2.28 g, y=54.3percent) was used for the following step.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 18, p. 4538 - 4541
[2] Patent: WO2006/44860, 2006, A2, . Location in patent: Page/Page column 43-44

4
[ 885223-63-2 ]
[ 676-58-4 ]
[ 886365-47-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 20, p. 5578 - 5585

5
[ 29241-65-4 ]
[ 886365-47-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 20, p. 5578 - 5585
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 790 - 793
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 18, p. 4538 - 4541

[ 886365-47-5 ] Synthesis Path-Downstream 1~47

1
[ 885223-63-2 ]
[ 75-16-1 ]
[ 886365-47-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran; at 0 - 20℃; for 0.5h;Inert atmosphere;	To a solution of compound4(2.0 g, 7.15 mmol) in anhydrous THF (15mL) was addedmethylmagnesium bromide(1M in THF, 8 mL, 8 mmol) dropwise at 0Cunderargon atmosphere. The resulting mixture was stirred at room temperaturefor 30 min. The reaction was quenched with sat. NH4Cl solution,diluted withwater(50 mL) and extracted with ethyl acetate (50 mL×3).The combined organic layers werewashed with water (50 mL) and brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=6:1, v/v) to give the title compound5as a yellow solid(1.5 g, 90% yield). 1H NMR (400 MHz, DMSO-d6) delta 8.71 (d,J= 2.5 Hz, 1H), 8.46 (d,J= 2.5 Hz, 1H), 2.62 (s, 3H).
54.3%	In tetrahydrofuran; at -78℃; for 3h;	Starting material 5-bromo-2- chloro-N-methoxy-N-methylnicotinamide (5.0 g, 17.89 mmol) was charged into a 250 ml round bottom flask and the flask was chilled to -78 0C. Methyl magnesium bromide 96.5 ml, 19.68 mmol) in 5 ml THF was added dropwise via addition funnel. The resulting mixture was allowed to stir for 3 hours at -78 0C. After removing the THF solvent via rotatory evaporation under reduced pressure, the reaction mixture was partitioned between ethylacetate and saturated aqueous sodium bicarbonate. After removing the ethylacetate, the resulting crude product was subject to a silica gel column with 20% ethylacetate in hexane. The resulting product (2.28 g, y=54.3%) was used for the following step.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4538 - 4541
[2]Patent: WO2006/44860,2006,A2 .Location in patent: Page/Page column 43-44

2
[ 886365-47-5 ]
5-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With hydrazine; at 20℃;	Starting material l-(5- bromo-2-chloropyridin-3-yl)ethanone (5.8 g, 24.7 mmol) and 100 ml anhydrous hydrazine was charged into 500 ml round bottom flask and the resulting mixture was allowed to stir at room temperature for overnight. After removing the excess hydrazine via rotatory evaporation under reduced pressure, the remaining residue was diluted with distilled water and solid was appeared. After filtering the water, the resulting solid was taken up in ethylacetate and saturated aqueous sodium bicarbonate and was extracted by ethylacetate twice. The combined organic layer was washed with water and brine and dried over sodium sulfate. The crude product was eluted through a short silica gel column (3 inch in length) with ethylacetate as a white solid (4.0 g, y=77%).
20%	With hydrazine; In ethanol; at 20℃;Product distribution / selectivity;	Preparation of 5-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine (D-2-6).A mixture of compound D-2-5 (4 g, 16 mmol) and hydrazine (30 mL) in ethanol (300 mL) was stirred at room temperature overnight. TLC (petroleum ether/EtOAc 5:1 ) indicated complete consumption of starting material. The reaction mixture was concentrated in vacuo and the residue was purified via column chromatography (silica gel, petroleum ether/EtOAc 15:1 ) to yield crude compound D-2-6, which was further purified by preparative HPLC to yield pure compound D-2-6 (800 mg, yield: 20%) as a white solid.

Reference： [1]Patent: WO2006/44860,2006,A2 .Location in patent: Page/Page column 43-44
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5578 - 5585
[3]Patent: WO2009/16460,2009,A2 .Location in patent: Page/Page column 105

3
[ 1111638-41-5 ]
[ 886365-47-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With pyridine; chromium(VI) oxide; In dichloromethane; at 0 - 20℃;Silica gel;	Preparation of 1-(5-bromo-2-chloropyridin-3-yl)ethanone (D-2-5). <n="106"/>To a stirred solution of pyridine (13 g, 0.165 mol) in CH2CI2 (200 mL) was added CrO3 (8.25 g, 0.083 mol) and silica gel (20 mL) portionwise at 0 C. After the addition, the reaction mixture was stirred for 10 minutes. Compound D-2-4 (6.5 g, 27.5 mmol) was then added and the resulting mixture was stirred at room temperature overnight. TLC (petroleum ether/EtOAc 8:1 ) indicated most of compound D-2-4 was consumed. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give crude compound D-2-5, which was purified by column chromatography (silica gel petroleum ether/EtOAc 20:1) to give pure compound D-2-5 (5 g, yield: 77%) as a yellow oil.

Reference： [1]Patent: WO2009/16460,2009,A2 .Location in patent: Page/Page column 104-105

4
[ 885223-63-2 ]
[ 676-58-4 ]
[ 886365-47-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5578 - 5585

5
[ 29241-65-4 ]
[ 886365-47-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5578 - 5585
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 790 - 793
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4538 - 4541

6
[ 886365-47-5 ]
[ 1401731-54-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5578 - 5585

7
[ 593-85-1 ]
[ 886365-47-5 ]
[ 1552301-50-4 ]

Yield	Reaction Conditions	Operation in experiment
42%	In dimethyl amine; at 135℃; for 3h;	A mixture of compound 12c (1.0 g, 4.26 mmol) and guanidine carbonate (1.04 g, 8.52 mmol) in DMA (25 mL) was stirred at 135 C for 3hrs. After cooling, the reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with water (50 mL×2) and brine (50 mL), dried over anhydrous Na 2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, dichloromethane/methanol/ammonium water 400:10:1, v/v) to give the title compound 12d (340 mg, 42% yield) as a brown solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 790 - 793

8
[ 885223-63-2 ]
[ 886365-47-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With methylmagnesium bromide; In tetrahydrofuran; at 0 - 20℃; for 0.5h;Inert atmosphere;	To a solution of compound 12b (2.0 g, 7.15 mmol) in anhydrous THF (15mL) was added methylmagnesium bromide (1M in THF, 8 mL, 8 mmol) dropwise at 0 C under Argon atmosphere. The resulting mixture was stirred at room temperature for 30 min. The reaction was quenched with sat. NH4Cl solution, diluted with water (50 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 6:1, v/v) to give the title compound 12c (1.5 g, 90% yield) as a yellow solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 790 - 793

9
[ 886365-47-5 ]
[ 1552301-52-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 790 - 793
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4538 - 4541

10
[ 886365-47-5 ]
N-(5-(2-amino-4-methylpyrido[2,3-d]pyrimidin-6-yl)-2-methoxypyridin-3-yl)butane-1-sulfonamide [ No CAS ]