[ CAS No. 1380089-33-7 ] {[proInfo.proName]}

Name: 1380089-33-7|(4-Bromo-3-methylisoxazol-5-yl)methyl acetate|97%
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SKU: A262561
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Quality Control of [ 1380089-33-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1380089-33-7 ]

SDS Specification

Alternatived Products of [ 1380089-33-7 ]

Product Details of [ 1380089-33-7 ]

CAS No. :	1380089-33-7	MDL No. :	MFCD24387374
Formula :	C₇H₈BrNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	USGKSLUGKUUZSM-UHFFFAOYSA-N
M.W :	234.05	Pubchem ID :	67814794
Synonyms :

Calculated chemistry of [ 1380089-33-7 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.43
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.03
TPSA :	52.33 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) :	-6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.34
Log Po/w (XLOGP3) :	1.18
Log Po/w (WLOGP) :	1.66
Log Po/w (MLOGP) :	0.83
Log Po/w (SILICOS-IT) :	2.1
Consensus Log Po/w :	1.62

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.14
Solubility :	1.68 mg/ml ; 0.00716 mol/l
Class :	Soluble
Log S (Ali) :	-1.87
Solubility :	3.12 mg/ml ; 0.0133 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.97
Solubility :	0.253 mg/ml ; 0.00108 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.5

Safety of [ 1380089-33-7 ]

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 [ 1380089-33-7 ]

* 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 [ 1380089-33-7 ]
Downstream synthetic route of [ 1380089-33-7 ]

[ 1380089-33-7 ] Synthesis Path-Upstream 1~6

1
[ 43214-88-6 ]
[ 1380089-33-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: With N-Bromosuccinimide In acetic acid at 110℃; for 1 h; Stage #2: With sodium hydrogencarbonate In acetic acid at 20℃;	[00237] (4-Bromo-3-methylisoxazol-5-yl)methyl acetate. . To a solution of (3- methylisoxazol-5-yl)methyl acetate (0.979 g, 6.31 mmol) in AcOH (10 mL, 175 mmol) was added N-bromosuccinimide (1.30 g, 7.30 mmol) and H₂SO₄ (0.65 mL, 12.19 mmol). The reaction was heated to 110 °C. After 1 h, the reaction mixture was cooled to roomtemperature and carefully poured into a beaker containing ice and saturated NaHC0₃. The bi- phasic was vigorously stirred and basic solution (pH -8-9) was extracted with EtOAc (2 x 15 mL). The organic layer was washed with 2percent sodium thiosulfate, washed with brine (20 mL), dried over Na₂S0₄, and concentrated to give a light yellow oil. The oil was purified on Biotage system (isocratic elution 10percent EtOAc : 90percent Hexanes) to give the titled compound (1.30 g, 5.55 mmol, 88percent Yield) as a colorless yellow oil. LC/MS m/z 234 [M+H]⁺.
88%	at 110℃; for 1 h;	To a solution of (3-methylisoxazol-5-yl)methyl acetate (0.979 g, 6.31 mmol) in AcOH (10 mL, 175 mmol) was added N-bromosuccinimide (1.30 g, 7.30 mmol) and H2SO4 (0.65 mL, 12.19 mmol). The reaction was heated to 110 °C. After 1 h, the reaction mixture was cooled to room temperature and carefully poured into a beaker containing ice and saturated NaHCO3. The bi-phasic mixture was vigorously stirred and basic solution (pH 8-9) was extracted with EtOAc (2 x 15 mL). The organic layer was washed with 2percent sodium thiosulfate, washed with brine (20 mL), dried over Na2SO4, and concentrated to give a light yellow oil. The oil was purified on Biotage system (isocratic elution 10percent EtOAc : 90percent Hexanes) to give the titled compound (1.30 g, 5.55 mmol, 88percent Yield) as a colorless yellow oil. LC/MS m/z 234 [M+H]⁺.
74.8%	at 110℃; for 1 h;	To a solution of (3-methylisoxazol-5-yl)methyl acetate (200 g, 1.29 mol) in AcOH (2.00 L) was added N-bromosuccinimide (230 g, 1.29 mol) and H2S04 (140 mL, 2.62 mol). The reaction was heated to 110 °C. After 1 h, the reaction mixture was cooled to room temperature and carefully poured into a beaker containing ice and saturated NaHCO3. The biphasic mixture was vigorously stirred and basic solution (pH —8-9) was extracted with EtOAc (2x). The organic layer was washed with 2percent sodium thiosulfate, washed with brine 0 dried over Na2SO4, and concentrated to give a light yellow oil. The oil was purified on Biotage system (isocratic elution 10percent EtOAc : 90percent Hexanes) to give the titled compound (225 g, 74.8percent yield) as a colorless yellow oil. LC/MS m/z 234 [M+H]⁺

31%

at 110℃; for 1 h;

To a solution of compound 12 ( 130 mg, 837.9 umol, 1 eq) in acetic acid (1.5 mL) was added NBS (178.9 mg, 1 mmoi, 1.2 eq) and sulfuric acid (164 mg, 1.7 mmoi, 2 eq). The reaction mixture was heated at 110 °C for 1 h when TLC showed the starting material was consumed completely. The reaction mixture was cooled to 25 °C and carefully poured into a vigorously stirred solution of ice cooled saturated NaHC0₃. The solution (pH 8-9) was extracted with EtOAc (3 x 20 mL). The combined organic fractions were washed with 2percent sodium thiosuifate (50 mL), brine(2 x 50 mL), dried over anhydrous Na₂S0₄, filtered and concentrated under vacuum. The residue was purified by column chromatography (0-10percent EtOAc in PE) to afford compound 13 (60 mg, 256.4 umol, 31percent yield) as a yellow oil: H-l NM R (400 MHz, CDCI₃) δ 2.14 (s, 3H), 2.32 (s, 3H), 5.17 (s, 2H).

Reference： [1] Patent: WO2012/75383, 2012, A2, . Location in patent: Page/Page column 82
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 9, p. 835 - 840
[3] Patent: WO2013/184878, 2013, A1, . Location in patent: Paragraph 00241; 00242
[4] Patent: WO2013/184876, 2013, A1, . Location in patent: Paragraph 00144; 00147; 00148
[5] Patent: WO2016/97870, 2016, A1, . Location in patent: Paragraph 0168
[6] Patent: WO2017/30814, 2017, A1, . Location in patent: Paragraph 00229

2
[ 14716-89-3 ]
[ 64-19-7 ]
[ 1380089-33-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	at 120℃; for 3 h;	To a solution of 20 (3.20 g, 28.32 mmol) in AcOH (5 mE) was addedN-bromosuccinimide (6.05 g, 33.98 mmol) and H2S04 (0.1 mE). The reaction mixture was heated to 120° C. for 3 h. The reaction mixture was concentrated, the residue was dissolved in EtOAc (200 mE), washed with saturated NaHCO3 (100 mE), saturated Na25203 (3x50 mE) and brine (100 mE). The organic layer was dried over sodium sulfate, filtered and concentrated to give 21(5.50 g, 83percent) as a pale yellow solid: ‘H NMR (300 MHz, CDC13) ö 5.16 (s, 2H), 2.31 (s, 3H), 2.13 (s, 3H).
83%	at 120℃; for 3 h;	General procedure: To a solution 20 (3.20g, 28.32mmol) in AcOH (5mL) was added N-bromosuccinimide(6.05g, 33.98mmol) and H2SO4 (0.1mL). The reaction mixture was heated to120 continued 3h. The reaction mixture was concentrated,The residue was dissolved in EtOAc (200mL) at, washed with saturatedNaHCO3 (100mL), saturated Na2S2O3 (3 × 50mL) and brine(100 mL) and washed. The organic layer was dried over sodium sulfate,filtered and concentrated to give a pale yellow solid of 21 (5.50g,83percent)

Reference： [1] Patent: US2016/145248, 2016, A1, . Location in patent: Paragraph 0305; 0306
[2] Patent: CN105473581, 2016, A, . Location in patent: Paragraph 0344; 0345; 0375; 0387
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 5, p. 1346 - 1350[4] Angew. Chem., 2018, vol. 130, p. 1360 - 1364,5

3
[ 627-09-8 ]
[ 1380089-33-7 ]

Reference： [1] Patent: WO2013/184876, 2013, A1,

4
[ 4857-42-5 ]
[ 1380089-33-7 ]

Reference： [1] Patent: WO2016/97870, 2016, A1,

5
[ 1004-96-2 ]
[ 1380089-33-7 ]

Reference： [1] Patent: WO2016/97870, 2016, A1,

6
[ 14716-89-3 ]
[ 1380089-33-7 ]

Reference： [1] Patent: WO2016/97870, 2016, A1,

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Yield	Reaction Conditions	Operation in experiment
	With triethylamine;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); at 110℃; for 4.0h;Inert atmosphere;	[00238] -Methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)isoxazol-5-yl)methylacetate. To a 500 mL flask (under N2 (g)) was addeddichlorobis(acetonitrile)palladium(II) (0.551 g, 2.12 mmol) and dicyclohexyl(2',6'- dimethoxybiphenyl-2-yl)phosphine (3.50 g, 8.53 mmol). To the solids were sequentially added a solution of <strong>[1380089-33-7](4-bromo-3-methylisoxazol-5-yl)methyl acetate</strong> (24.8 g, 106 mmol) in 1,4-dioxane (65 mL), Et3N (44.3 mL, 318 mmol), and 4,4,5,5-tetramethyl- 1,3,2- dioxaborolane (24 mL, 160 mmol). The flask was sequentially evacuated and purged under N2, and this process was repeated three times. The reaction mixture was heated to 110 C (under a constant stream of N2 (g)) and allowed to stir for -4 h. LC-MS analysis at this point showed complete conversion of the starting bromo-isoxazole. The reaction mixture was cooled to room temperature and EtOAc (100 mL) was added. After 15 min of stirring, the suspension was filtered over a pad of Celite. The filter cake was washed with EtOAc (3 x 100 mL), concentrated in vacuo, and the solvent was switched using 1,4-Dioxane (2 x 50 mL). The borate ester with used without further purification.
	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); triethylamine; In 1,4-dioxane; at 110℃; for 4.0h;Inert atmosphere;	To a 500 mL flask (under N2 (g)) was added dichlorobis(acetonitrile)palladium(II) (0.55 1 g, 2.12 mmol) and dicyclohexyl(2?,6?- dimethoxybiphenyl-2-yl)phosphine (3.50 g, 8.53 mmol). To the solids were sequentially added a solution of <strong>[1380089-33-7](4-bromo-3-methylisoxazol-5-yl)methyl acetate</strong> (24.8 g, 106 mmol) in 1,4-dioxane (65 mL), Et3N (44.3 mL, 318 mmol), and 4,4,5,5-tetramethyl-1,3,2- dioxaborolane (24.0 mL, 160 mmol). The flask was sequentially evacuated and purged under N2, and this process was repeated three times. The reaction mixture was heated to 110 C (under a constant stream of N2 (g)) and allowed to stir for -4 h. LC-MS analysis at this point showed complete conversion of the starting bromo-isoxazole. The reaction mixture was cooled to room temperature and EtOAc (100 mL) was added. After 15 mm of stirring, the suspension was filtered over a pad of Celite. The filter cake was washed with EtOAc (3 x 100 mL), concentrated in vacuo, and the solvent was switched using 1,4-Dioxane (2 x 50 mL). The borate ester with used without further purification.
12 g	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); triethylamine; In 1,4-dioxane; at 110℃; for 16.3333h;Inert atmosphere;	To a 200 mL flask (under N2) was added dichlorobis(acetonitrile)palladium(II)(0.22 g, 0.85 mmol) and dicyclohexyl(2?,6?-dimethoxybiphenyl-2-yl)phosphine (1.40 g, 3.41 mmol). To the solid were sequentially added a solution of(4-bromo-3-methyl- isoxazol-5y1)methyl acetate (10.0 g, 42.73 mmol) in dry 1,4-dioxane (100 mL), dry Et3N(17.82 mL, 128.20 mmol), and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15.50 mL,106.83 mmol). The flask was sequentially evacuated, purged under N2, and repeated for20 mm. The mixture was heated to 110 C (under N2) for 16 h. The mixture was cooledto RT and filtered through celite pad followed by washing with EtOAc. The filtrate wasconcentrated under reduced pressure. The residue was used for further step withoutfurther purification (12.0 g). ?H NMR (400 MHz, CDC13): oe 5.31 (s, 2H), 2.37 (s, 3H),2.11 (s, 12H).

31%	With N-Bromosuccinimide; sulfuric acid; acetic acid; at 110℃; for 1.0h;	To a solution of compound 12 ( 130 mg, 837.9 umol, 1 eq) in acetic acid (1.5 mL) was added NBS (178.9 mg, 1 mmoi, 1.2 eq) and sulfuric acid (164 mg, 1.7 mmoi, 2 eq). The reaction mixture was heated at 110 C for 1 h when TLC showed the starting material was consumed completely. The reaction mixture was cooled to 25 C and carefully poured into a vigorously stirred solution of ice cooled saturated NaHC03. The solution (pH 8-9) was extracted with EtOAc (3 x 20 mL). The combined organic fractions were washed with 2% sodium thiosuifate (50 mL), brine(2 x 50 mL), dried over anhydrous Na2S04, filtered and concentrated under vacuum. The residue was purified by column chromatography (0-10% EtOAc in PE) to afford compound 13 (60 mg, 256.4 umol, 31% yield) as a yellow oil: H-l NM R (400 MHz, CDCI3) delta 2.14 (s, 3H), 2.32 (s, 3H), 5.17 (s, 2H).
	With N-Bromosuccinimide;	The synthesis of PTM-l-B was carried out according to the above scheme as described in the literature (J. Med. Chem. 2016, 59, 1330-1339). PTM-l-B is the carboxylic acid of CPI- 0610 reported in the literature.

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
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
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H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
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
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
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
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
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. 1380089-33-7 ] {[proInfo.proName]}

Quality Control of [ 1380089-33-7 ]

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[ 1380089-33-7 ] Synthesis Path-Upstream 1~6

[ 1380089-33-7 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 1380089-33-7 ]

Bromides

Esters

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Isoxazoles

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[ 1380089-33-7 ]

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[ 1380089-33-7 ]