1259396-11-6|Methyl 5-bromo-2-methylthiophene-3-carboxylate| Ambeed

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Quality Control of [ 1259396-11-6 ] Purity: 95% (stabilized with Cu+HQ+MgO) SDS Specification

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Product Details of [ 1259396-11-6 ]

CAS No. :	1259396-11-6
Formula :	C₇H₇BrO₂S
M.W :	235.10
SMILES Code :	O=C(C1=C(C)SC(Br)=C1)OC
MDL No. :	MFCD14636529
InChI Key :	KOLUIHOYXGOSFO-UHFFFAOYSA-N
Pubchem ID :	57839448

Safety of [ 1259396-11-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1259396-11-6 ]

* 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.

Downstream synthetic route of [ 1259396-11-6 ]

[ 1259396-11-6 ] Synthesis Path-Downstream 1~35

1
[ 1918-78-1 ]
[ 1259396-11-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.
[2]Patent: US2012/101137,2012,A1 .
[3]European Journal of Medicinal Chemistry,2015,vol. 102,p. 471 - 476.
[4]European Journal of Medicinal Chemistry,2018,vol. 156,p. 269 - 294.

2
[ 1259396-11-6 ]
[ 1334598-73-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.

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[ 1334598-77-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.

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[ 1334598-01-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.

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[ 1334598-04-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.

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[ 1334598-15-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.

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[ 1334598-18-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.

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[ 1334598-23-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.

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[ 1334598-64-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.

10
[ 1259396-11-6 ]
(2-(methylsulfonyl)-phenyl)boronic acid [ No CAS ]
[ 1334598-50-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.

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[ 308103-40-4 ]
[ 1334598-41-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.

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2-(aminocarbonyl)benzeneboronic acid [ No CAS ]
[ 1334598-54-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.

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[ 53562-51-9 ]
[ 1259396-11-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃;	To a solution of 10 (156g, 999mmol) in DMF (750mL), NBS (178g, 1.00mol) was added at room temperature and stirred overnight. The reaction mixture was diluted with water and extracted with n-hexane. The organic layer was washed with saturated aqueous NaHCO3 and brine and dried over Na2SO4. After filtration, the solvent was concentrated under reduced pressure to give 226g (96%) of 11 as a yellow oil: 1H NMR (400MHz, CDCl3) delta 7.33 (s, 1H), 3.83 (s, 3H), 2.67 (s, 3H).
93%	With N-Bromosuccinimide; acetic acid; In N,N-dimethyl-formamide; at 20℃; for 16h;	A mixture of methyl 2-methylthiophene-3-carboxylate (23.3 g, 0.15 mmol), N-bromosuccinimide (31.8 g, 0.18 mmol) in acetic acid (8.94 g, 0.15 mmol) and dimethylformamide (250 mL) was stirred at room temperature for 16 hours. The mixture was filtered through a pad of silica gel (petroleum ether) to afford the desired product (35 g, 93% yield).
70%	With N-Bromosuccinimide; acetic acid; at 20℃; for 18h;	Methyl 2-methylthiophene-3-carboxylate (4.62 g, 29.6 mmol) was dissolved in DMF (23 mL) and AcOH (15 mL). N-Bromosuccinimide (5.54 g, 29.6 mmol) was added and the reaction was stirred at RT for 18 h. The mixture was evaporated to dryness then dissolved in EA and washed with sat. aq. NaHCO3 to give methyl 5-bromo-2-methylthiophene-3-carboxylate (4.90 g, 70%) as an orange oil. MS (M+1) 236.1.

70%	With N-Bromosuccinimide; In acetic acid; N,N-dimethyl-formamide; at 0 - 25℃; for 15h;	The compound 2-methylthiophene-3-carboxylic acid methyl ester (10.0 g, 64.0 mmol) was dissolved in a mixed solution of N,N-dimethylformamide (50 mL) and acetic acid (50 mL).N-bromosuccinimide (11.4 g, 64.0 mmol) was slowly added at 0 C, and the reaction was carried out at 25 C for 15 hours.After the reaction was completed, the reaction liquid was concentrated, and 1 L of ethyl acetate was added, and the mixture was washed three times with a saturated aqueous sodium chloride solution (1 L×3).The organic phase was dried and concentrated and the residue was purified by medium-pressure preparative column chromatography (0-80% methanol, gradient) to give the title compound 10.5g,The yield was 70.0%.
	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃;	2-Methylthiophene-3-carboxylic acid methyl ester (156 g) was dissolved in N,N-dimethylformamide (750 mL), N-bromosuccinimide (178 g) was added thereto, and stirring was conducted overnight at room temperature. Water was added to the reaction liquid, and extraction was conducted by using hexane. The organic phase was washed sequentially with an aqueous sodium hydrogen sulfate solution and saturated brine and dried over anhydrous sodium sulfate. Filtration was conducted, and the filtrate was then concentrated under a reduced pressure to give the title compound (226 g).1H-NMR (CDCl3) delta (ppm): 2.67 (3H, s), 3.84 (3H, s), 7.33 (1H, s).
16.1 g	With N-Bromosuccinimide; acetic acid; In N,N-dimethyl-formamide;	3 (12.00 g, 76.82 mmol) was dissolved in 100 ml DMF/aceticacid (3:2). N-bromosuccinimide (13.70 g, 77.00 mmol) was added at room temperature andstirred overnight. Thereaction mixture was diluted with H2O(30 ml) and extractedwith ethyl acetate (60 ml ×2). The organic phase waswashed with saturated aqueous sodium bisulfate solution (30 ml) and saturated brine solution (30 ml), dried over Na2SO4,and filtrated, then the solvent was evaporated under reduced pressure to give 4(16.10 g, 789.1%) as a pale yellow viscous oil. 1H NMR (400 MHz, CDCl3)delta 7.33 (s, 1H), 3.84 (s, 3H), 2.67 (s, 3H). MS (EI) m/z: 235 (M+).

References: [1]European Journal of Medicinal Chemistry,2018,vol. 156,p. 269 - 294.
[2]Patent: WO2018/68017,2018,A1 .Location in patent: Page/Page column 132.
[3]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5417 - 5422.
[4]Patent: US2018/170948,2018,A1 .Location in patent: Paragraph 0406.
[5]Patent: CN110294746,2019,A .Location in patent: Paragraph 0176; 0189-0191.
[6]Patent: US2012/101137,2012,A1 .Location in patent: Page/Page column 14.
[7]European Journal of Medicinal Chemistry,2015,vol. 102,p. 471 - 476.

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[ 1259396-19-4 ]

References: [1]Patent: US2012/101137,2012,A1 .

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[ 1259396-20-7 ]

References: [1]Patent: US2012/101137,2012,A1 .
[2]European Journal of Medicinal Chemistry,2018,vol. 156,p. 269 - 294.

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[ 1259396-23-0 ]

References: [1]Patent: US2012/101137,2012,A1 .
[2]European Journal of Medicinal Chemistry,2018,vol. 156,p. 269 - 294.

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[ 1259396-11-6 ]
[ 1259396-26-3 ]

References: [1]Patent: US2012/101137,2012,A1 .
[2]European Journal of Medicinal Chemistry,2018,vol. 156,p. 269 - 294.

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[ 1259396-41-2 ]

References: [1]European Journal of Medicinal Chemistry,2018,vol. 156,p. 269 - 294.

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[ 85909-08-6 ]
[ 1259396-18-3 ]

Yield	Reaction Conditions	Operation in experiment
		Under an argon atmosphere, <strong>[1259396-11-6]5-bromo-2-methylthiophene-3-carboxylic acid methyl ester</strong> (2.00 g) was dissolved in tetrahydrofuran (9.47 mL), isopropylmagnesium bromide (12.9 mL) was added dropwise thereto at -40 C., and stirring was conducted for 1.5 hours. A solution of 2-oxopyrrolidine-1-carboxylic acid t-butyl ester (1.89 g) in tetrahydrofuran (11.2 mL) was added dropwise at -40 C., and stirred at room temperature for 24 hours. The reaction liquid was cooled to -10 C., methanol (17.2 mL) was added thereto, sodium borohydrate (486 mg) was then added thereto in portions, and stirring was conducted for 15 minutes. A saturated aqueous ammonium chloride solution was added to the reaction liquid, and the reaction liquid was extracted with chloroform and dried over anhydrous sodium sulfate. Filtration was conducted, the filtrate was then concentrated under a reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane/ethyl acetate=1/1) to give the title compound (2.13 g) as a yellow oily substance.1H-NMR (CDCl3) delta (ppm): 1.44 (9H, s), 1.51-1.69 (4H, m), 1.79-1.84 (1H, m), 2.70 (3H, s), 3.15-3.19 (1H, m), 3.83 (3H, s), 4.57-4.87 (1H, m), 7.26 (1H, s).

References: [1]Patent: US2012/101137,2012,A1 .Location in patent: Page/Page column 15.

21
[ 1259396-11-6 ]
[ 320343-59-7 ]
[ 1259396-12-7 ]

Yield	Reaction Conditions	Operation in experiment
		Under an argon atmosphere, <strong>[1259396-11-6]5-bromo-2-methylthiophene-3-carboxylic acid methyl ester</strong> (227 g) was dissolved in tetrahydrofuran (350 mL) and cooled to 0 C. Isopropylmagnesium bromide (1500 mL) was added dropwise thereto at 10 C. or less, and stirring was conducted at 0 C. for 2 hours.A solution of (S)-4-(t-butyldimethylsilanyloxy)-2-oxopyrrolidine-1-carboxylic acid t-butyl ester (276 g) in tetrahydrofuran (550 mL) was then added dropwise thereto at 10 C. or less, and stirring was conducted at room temperature for 1.5 hours. The reaction liquid was cooled to 0 C., a 30% aqueous citric acid solution was added dropwise thereto at 10 C. or less to adjust the pH 3, and stirring was conducted at room temperature for 1.5 hours. Ethyl acetate was added to the reaction liquid, and the organic phase was washed sequentially by a 5% aqueous sodium hydrogen carbonate solution and saturated brine and dried over anhydrous sodium sulfate. Filtration was conducted, and the filtrate was then concentrated under a reduced pressure to give a crude product (418 g).Under an argon atmosphere, (R)-5,5-diphenyl-2-methyl-3,4-propano-1,3,2-oxazborolidine (49.1 g) was dissolved in tetrahydrofuran (86 mL), a boran-dimethylsulfide complex (886 mL) was added dropwise thereto at room temperature, and stirring was conducted for 20 minutes. A solution of the above-mentioned crude product (418 g) in tetrahydrofuran (450 mL) was then added dropwise thereto at room temperature over 45 minutes, and stirring was conducted for 30 minutes. The reaction liquid was cooled to 0 C., methanol/saturated brine was added dropwise thereto, ethyl acetate was then added thereto, and the organic phase was washed with saturated brine and dried over anhydrous sodium sulfate. Filtration was conducted, the obtained filtrate was then concentrated under a reduced pressure, and the obtained residue was passed through a short column of a silica gel (ethyl acetate/hexane=1/2) to give a crude product (337 g).Under an argon atmosphere, the above-mentioned crude product (302 g) and triethylamine (265 mL) were dissolved in methylene chloride (800 mL), a solution of methanesulfonyl chloride (73.8 mL) in methylene chloride (295 mL) was added dropwise thereto at 0 C., and stirring was conducted for 30 minutes. Water was added to the reaction liquid, extraction was conducted by using methylene chloride, and the organic phase was dried over anhydrous sodium sulfate. Filtration was conducted, and the filtrate was then concentrated under a reduced pressure to give a crude product (304 g).The above-mentioned crude product (265 g) was dissolved in tetrahydrofuran (265 mL), tetrabutylammonium fluoride (565 mL) was added dropwise thereto at room temperature, and stirring was conducted continuously for 1.5 hours. The reaction liquid was concentrated under a reduced pressure, extracted with ethyl acetate, washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. Filtration was conducted, the filtrate was then concentrated under a reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/5-2/1) to give the title compound (128 g) as a yellow white solid.1H-NMR (CDCl3) delta (ppm): 1.24-1.45 (9H, m), 1.66 (1H, t, J=4.9 Hz), 2.18 (1H, d, J=14.3 Hz), 2.35-2.51 (1H, m), 2.71 (3H, s), 3.51 (1H, d, J=11.7 Hz), 3.66 (1H, t, J=7.7 Hz), 3.83 (3H, s), 4.48-4.58 (1H, m), 5.09 (1H, b r.s), 7.16-7.21 (1H, m).ESI/MS (m/z): 342 (M+H)+, 340 (M-H)-.

References: [1]Patent: US2012/101137,2012,A1 .Location in patent: Page/Page column 14; 15.

22
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[ 1259396-17-2 ]
[ 1259396-16-1 ]

References: [1]Patent: US2012/101137,2012,A1 .

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[ 1259396-24-1 ]

References: [1]Patent: US2012/101137,2012,A1 .

24
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[ 1259396-30-9 ]

References: [1]Patent: US2012/101137,2012,A1 .

25
[ 1259396-11-6 ]
(-)-2-methyl-5-pyrrolidin-2-ylthiophene-3-carboxylic acid methyl ester (-)-dibenzoyl-L-tartrate [ No CAS ]

References: [1]Patent: US2012/101137,2012,A1 .

26
[ 1259396-11-6 ]
(-)-2-(4-carboxy-5-methylthiophen-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Patent: US2012/101137,2012,A1 .

27
[ 1259396-11-6 ]
(-)-2-[4-(5-fluorothiazol-2-ylcarbamoyl)-5-methylthiophen-2-yl]pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Patent: US2012/101137,2012,A1 .

28
[ 1259396-11-6 ]
C₁₅H₂₀ClNO₃S [ No CAS ]

References: [1]Patent: US2012/101137,2012,A1 .

29
[ 1259396-11-6 ]
C₁₅H₁₉ClFNO₃S [ No CAS ]

References: [1]Patent: US2012/101137,2012,A1 .

30
[ 1259396-11-6 ]
C₁₅H₂₀ClNO₃S [ No CAS ]

References: [1]Patent: US2012/101137,2012,A1 .

31
[ 1259396-11-6 ]
(-)-2-methyl-5-pyrrolidin-2-ylthiophene-3-carboxylic acid (5-fluorothiazol-2-yl)amide [ No CAS ]

References: [1]Patent: US2012/101137,2012,A1 .

32
[ 1259396-11-6 ]
(-)-2-methyl-5-[1-(2-ureidoacetyl)pyrrolidin-2-yl]thiophene-3-carboxylic acid (5-fluorothiazol-2-yl)amide [ No CAS ]

References: [1]Patent: US2012/101137,2012,A1 .

33
[ 1259396-11-6 ]
[ 1467070-68-3 ]

References: [1]Patent: WO2013/149940,2013,A1 .

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[ 1259396-11-6 ]
[ 1467070-86-5 ]

References: [1]Patent: WO2013/149940,2013,A1 .

35
[ 1259396-11-6 ]
[ 1467070-89-8 ]

References: [1]Patent: WO2013/149940,2013,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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[ 1259396-11-6 ]

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P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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
H227	Combustible liquid
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

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CAS No.: 1259396-11-6

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