[ CAS No. 1190862-70-4 ] {[proInfo.proName]}

Name: 1190862-70-4|Ethyl 5-bromo-6-methylnicotinate|97%
Brand: Ambeed
SKU: A184656
Rating: 90 (22 reviews)

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Quality Control of [ 1190862-70-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1190862-70-4 ]

SDS Specification

Alternatived Products of [ 1190862-70-4 ]

Product Details of [ 1190862-70-4 ]

CAS No. :	1190862-70-4	MDL No. :	MFCD19440560
Formula :	C₉H₁₀BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AFNPRVLCAREGEN-UHFFFAOYSA-N
M.W :	244.09	Pubchem ID :	58170478
Synonyms :

Calculated chemistry of [ 1190862-70-4 ]

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 :	0.0
Molar Refractivity :	52.99
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) :	-6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.52
Log Po/w (XLOGP3) :	2.16
Log Po/w (WLOGP) :	2.33
Log Po/w (MLOGP) :	1.7
Log Po/w (SILICOS-IT) :	2.67
Consensus Log Po/w :	2.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.86
Solubility :	0.339 mg/ml ; 0.00139 mol/l
Class :	Soluble
Log S (Ali) :	-2.62
Solubility :	0.591 mg/ml ; 0.00242 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.75
Solubility :	0.0432 mg/ml ; 0.000177 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.89

Safety of [ 1190862-70-4 ]

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

Application In Synthesis of [ 1190862-70-4 ]

* 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 [ 1190862-70-4 ]
Downstream synthetic route of [ 1190862-70-4 ]

[ 1190862-70-4 ] Synthesis Path-Upstream 1~2

1
[ 1190862-70-4 ]
[ 1190862-72-6 ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: With water; sodium hydroxide In ethanol at 20℃; for 3 h; Stage #2: With hydrogenchloride In ethanol; water	2M Aqueous sodium hydroxide solution (1.91 mL, 3.8 mmol) was added to a stirred solution of ethyl 5-bromo-6-methylnicotinate (preparation 47c, 0.41 g, 1.7 mmol) in ethanol (14 mL) at room temperature. After 3 hours, the solvent was evaporated and water was added to the residue. The pH was adjusted to 4-5 with concentrated hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried (MgSO₄) and evaporated to give the title compound (0.16 g, 43percent) as a white solid. LRMS (m/z): 216/218 (M+1)⁺.

Reference： [1] Patent: EP2108641, 2009, A1, . Location in patent: Page/Page column 55-56

2
[ 13061-96-6 ]
[ 1190862-68-0 ]
[ 1190862-70-4 ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium carbonate In 1,4-dioxane at 110℃; for 72 h; Inert atmosphere	An oven-dried resealable Schlenk tube was charged with ethyl 5,6-dibromonicotinate (preparation 47b, 1.09 g, 3.5 mmol), methylboronic acid (0.24 g, 4.0 mmol), potassium carbonate (1.46 g, 10.6 mmol) and 1,4-dioxane (27 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and then tetrakis(triphenylphosphine)palladium(0) (0.41 g, 0.35 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was sealed and the mixture was stirred and heated in an oil bath to 110 °C. After 3 days, the mixture was cooled, filtered through Celite.(R). and the filtrate was evaporated. Purification of the residue by flash chromatography (97:3 to 9:1 hexanes/ethyl acetate) gave the title compound (0.41 g, 45percent) as a solid. LRMS (m/z): 244/246 (M+1)⁺. ¹H-NMR δ (CDCl₃): 1.41 (t, J=9.0Hz, 3H), 2.74 (s, 3H), 4.41 (q, J=9.0Hz, 2H), 8.40 (d, J=3.0Hz, 1H), 9.01 (d, J=3.0Hz, 1H).

Reference： [1] Patent: EP2108641, 2009, A1, . Location in patent: Page/Page column 55-56

[ 1190862-70-4 ] Synthesis Path-Downstream 1~8

1
[ 1190862-70-4 ]
[ 1190862-72-6 ]

Yield	Reaction Conditions	Operation in experiment
43%		2M Aqueous sodium hydroxide solution (1.91 mL, 3.8 mmol) was added to a stirred solution of <strong>[1190862-70-4]ethyl 5-bromo-6-methylnicotinate</strong> (preparation 47c, 0.41 g, 1.7 mmol) in ethanol (14 mL) at room temperature. After 3 hours, the solvent was evaporated and water was added to the residue. The pH was adjusted to 4-5 with concentrated hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried (MgSO4) and evaporated to give the title compound (0.16 g, 43%) as a white solid. LRMS (m/z): 216/218 (M+1)+.

Reference： [1]Patent: EP2108641,2009,A1 .Location in patent: Page/Page column 55-56

2
[ 13061-96-6 ]
[ 1190862-68-0 ]
[ 1190862-70-4 ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 110℃; for 72h;Inert atmosphere;	An oven-dried resealable Schlenk tube was charged with ethyl 5,6-dibromonicotinate (preparation 47b, 1.09 g, 3.5 mmol), methylboronic acid (0.24 g, 4.0 mmol), potassium carbonate (1.46 g, 10.6 mmol) and 1,4-dioxane (27 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and then tetrakis(triphenylphosphine)palladium(0) (0.41 g, 0.35 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was sealed and the mixture was stirred and heated in an oil bath to 110 C. After 3 days, the mixture was cooled, filtered through Celite and the filtrate was evaporated. Purification of the residue by flash chromatography (97:3 to 9:1 hexanes/ethyl acetate) gave the title compound (0.41 g, 45%) as a solid. LRMS (m/z): 244/246 (M+1)+. 1H-NMR delta (CDCl3): 1.41 (t, J=9.0Hz, 3H), 2.74 (s, 3H), 4.41 (q, J=9.0Hz, 2H), 8.40 (d, J=3.0Hz, 1H), 9.01 (d, J=3.0Hz, 1H).

Reference： [1]Patent: EP2108641,2009,A1 .Location in patent: Page/Page column 55-56

3
[ 1190862-70-4 ]
7-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-(di-tert-butoxycarbonyl)amine [ No CAS ]
C₂₅H₃₁N₅O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		17C: A mixture of 1A (250 mg, 0.605 mmol), bis(pinacolato)diboron (192 mg,0.756 mmol), potassium acetate (178 mg, 1.815 mmol) and PdC12(dppf)-CH2C12 adduct (24.70 mg, 0.030 mmol) in dioxane (6 mL) was heated at 100 C for 60 mm. After cooling to rt, <strong>[1190862-70-4]ethyl 5-bromo-6-methylnicotinate</strong> (150 mg, 0.615 mmol) and1,1 ?-bis(di-tert-butylphosphino)ferrocenepalladium dichloride (20.03 mg, 0.031 mmol) were added. The reaction mixture was degassed by nitrogen sparge for 5 mm. 2M K3P04 (aq) (0.922 mL, 1.844 mmol) was quickly added and the reaction mixture heated at 100 C for 15 mm. After cooling to rt, volatiles were removed in vacuo. The cmde residue was purified with column chromatography on the Isco system (40 g, 0-100%EtOAc/Hex to afford 17C (300 mg, 0.573 mmol, 93 % yield) as a crystalline beige solid. MS ESI m/z 498.0 (M+H)

Reference： [1]Patent: WO2018/148626,2018,A1 .Location in patent: Page/Page column 81

4
[ 1190862-70-4 ]
C₇H₃⁽²⁾H₃BrNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
784 mg	With [D]-sodium hydroxide; In water; at 140℃;	Ethyl 5-bromo-6-methyl-pyridine-3-carboxylate (1 g, 4.1 mmol) was dissolved in heavy water (10 mL).Deuterated sodium hydroxide (1.51 g, 14.75 mmol) was added thereto, and the reaction solution was heated to 140 C overnight.After the reaction was completed, it was cooled to room temperature, and the pH was adjusted to 3-4 with a 2N aqueous HCl solution, and the precipitated solid was filtered, washed with a small amount of water, and dried.A white solid 784 mg was obtained.

Reference： [1]Patent: CN104341425,2018,B .Location in patent: Paragraph 0236; 0238; 0239; 0240

5
[ 1190862-70-4 ]
ethyl 5-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-6-methylnicotinate [ No CAS ]

Reference： [1]Patent: WO2019/89442,2019,A1

6
[ 1190862-70-4 ]
5-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-6-methylnicotinic acid, lithium salt [ No CAS ]

Reference： [1]Patent: WO2019/89442,2019,A1

7
[ 1190862-70-4 ]
N-[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-6-methylpyridine-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2019/89442,2019,A1

8
[ 1190862-70-4 ]
[ 73183-34-3 ]
ethyl 6-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.0%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 60℃;	16A: Ethyl 6-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate : A degassed solution of <strong>[1190862-70-4]ethyl 5-bromo-6-methylnicotinate</strong> (600 nig, 2.458 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (874 mg, 3.44 mmol), potassium acetate (374 mg, 3.81 mmol) and PdCl2(dppf)-CH2Cl2 adduct (161 mg, 0.197 mmol) in dioxane (10 mL) was heated to 60 C with vigorous mixing ON. The reaction mixture was concentrated onto Celite, then purified by flash chomatography utilizing a 40g ISCO column and eluting with 0-90% EtOAc in hexanes. The pure fractions were concentrated to afford ethyl 6-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (490 mg, 1.599 mmol, 65.0 % yield) as a waxy white solid. MSESI m/z 291.8 (M+H)

Reference： [1]Patent: WO2019/89442,2019,A1 .Location in patent: Page/Page column 82

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[ 1190862-70-4 ]

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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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H220	Extremely flammable gas
H221	Flammable gas
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Health hazards
Code	Phrase
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
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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H336	May cause drowsiness or dizziness
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H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
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. 1190862-70-4 ] {[proInfo.proName]}

Quality Control of [ 1190862-70-4 ]

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Calculated chemistry of [ 1190862-70-4 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1190862-70-4 ]

Application In Synthesis of [ 1190862-70-4 ]

[ 1190862-70-4 ] Synthesis Path-Upstream 1~2

[ 1190862-70-4 ] Synthesis Path-Downstream 1~8

Related Functional Groups of [ 1190862-70-4 ]

Bromides

Esters

Related Parent Nucleus of [ 1190862-70-4 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

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Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1190862-70-4 ]

Related Parent Nucleus of
[ 1190862-70-4 ]