425392-44-5|Ethyl 2-bromo-5-chlorothiazole-4-carboxylate| Ambeed

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Quality Control of [ 425392-44-5 ] Purity: 98% SDS Specification

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Product Details of [ 425392-44-5 ]

CAS No. :	425392-44-5
Formula :	C₆H₅BrClNO₂S
M.W :	270.53
SMILES Code :	O=C(C1=C(Cl)SC(Br)=N1)OCC
MDL No. :	MFCD08704625
InChI Key :	GNUVSLOHOLUDJE-UHFFFAOYSA-N
Pubchem ID :	11196524

Safety of [ 425392-44-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 425392-44-5 ]

* 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.

Downstream synthetic route of [ 425392-44-5 ]

[ 425392-44-5 ] Synthesis Path-Downstream 1~18

1
[ 5720-07-0 ]
[ 425392-44-5 ]
[ 425392-48-9 ]

References: [1]Organic Letters,2002,vol. 4,p. 1363 - 1365.

2
[ 5720-06-9 ]
[ 425392-44-5 ]
5-chloro-2-(2-methoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 1363 - 1365.

3
[ 7486-35-3 ]
[ 425392-44-5 ]
5-chloro-2-vinyl-thiazole-4-carboxylic acid ethyl ester [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 1363 - 1365.

4
[ 136539-01-0 ]
[ 425392-44-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 80℃;	Tert-butyl nitrite (1.5 eq, 34.8 mmol) and copper (II) bromide (1.5 eq, 34.8) were dissolved in acetonitrile (180 mL). Ethyl 2-amino-5-chlorothiazole-4-carboxylate (1 eq, 23.2 mmol) in acetonitrile (60 mL) was added by dropping funnel over 45 min and upon complete addition the reaction stirred at 80 C overnight. The reaction was determined to be complete by TLC (4: 1 Hex/EtOAc). The reaction was concentrated in vacuo, taken up in NaHCCb, and extracted with EtOAc (50 mL x 3). The organics were collected and washed with brine (100 mL), dried with Na2S04, filtered and concentrated to give the title compound in quantitative yield.
46%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 80℃; for 2.0h;	A solution of ethyl 2-amino-5-chloro-l,3-thiazole-4-carboxylate (2.00 g, 9.678 mmol, 1.00 equiv), tert-butyl nitrite (1.20 g, 11.637 mmol, 1.20 equiv), cupric bromide (2.59 g, 11.596 mmol, 1.20 equiv) in acetonitrile (50 mL) was stirred for 2 h at 80 C. The resulting solution was concentrated under vacuum and the residue was purified by a silica gel column chromatography eluted with dichloromethane/methanol (40:1) to give the title compound (1.2 g, 46%) as a white solid. LC-MS (ES, m/z): 270 [M+H]+.
	With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 5 - 65℃;	16.2. 2-Bromo-5-chloro-thiazole-4-carboxylic acid ethyl esterTo a suspension of CuBr2 (250.8 mg) in CH3CN (4 mL) was added at 5C isopentyl nitrite (0.23 mL). After stirring for 5 min was added in portions at 5C intermediate 16.1. ELN145- 0048.2. (281.8 mg) and the reaction mixture was carefully heated to 65C for 1.5 h. The reaction mixture was evaporated to dryness, the residue diluted with H2O and stirred at RT for I h. The precipitate was filtrated and washed with H2O, CH2Cl2 (5x1.5 mL). The filtrate was evaporated, the residue taken up in Et2O (4 mL) and stirred at RT overnight. The mixture was filtrated, taken up in Hept (1.5 mL), stirred for 1 h again, filtrated and evaporated to dryness to give 224 mg of the desired product. 1H NMR δ, 4.46 (q, 2 H), 1.44 (t, 3 H).

References: [1]Patent: WO2019/40511,2019,A1 .Location in patent: Paragraph 00286.
[2]Organic Letters,2003,vol. 5,p. 2911 - 2914.
[3]Organic Letters,2002,vol. 4,p. 1363 - 1365.
[4]Patent: WO2016/135163,2016,A1 .Location in patent: Paragraph 0209.
[5]Tetrahedron Letters,2002,vol. 43,p. 7051 - 7053.
[6]Patent: WO2010/122504,2010,A1 .Location in patent: Page/Page column 54.
[7]ChemMedChem,2020,vol. 15,p. 1691 - 1698.

5
[ 536-74-3 ]
[ 425392-44-5 ]
5-chloro-2-phenylethynyl-thiazole-4-carboxylic acid ethyl ester [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 1363 - 1365.

6
pyridin-2-ylzinc(II) bromide [ No CAS ]
[ 425392-44-5 ]
5-chloro-2-pyridin-2-yl-thiazole-4-carboxylic acid ethyl ester [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 1363 - 1365.

7
[ 425392-44-5 ]
[ 98-80-6 ]
[ 59937-01-8 ]
[ 425392-45-6 ]
[ 425392-46-7 ]

References: [1]Organic Letters,2002,vol. 4,p. 1363 - 1365.

8
[ 425392-44-5 ]
2-bromo-5-chlorothiazole-4-carboxylic acid [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 7051 - 7053.

9
[ 122775-35-3 ]
[ 425392-44-5 ]
5-chloro-2-(3,4-dimethoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester [ No CAS ]

References: [1]Organic Letters,2003,vol. 5,p. 2911 - 2914.

10
[ 5398-36-7 ]
[ 425392-44-5 ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 7051 - 7053.
[2]Organic Letters,2002,vol. 4,p. 1363 - 1365.
[3]Patent: WO2016/135163,2016,A1 .
[4]ChemMedChem,2020,vol. 15,p. 1691 - 1698.

11
[ 425392-44-5 ]
2-(4-methoxy-phenyl)-5-phenyl-thiazole-4-carboxylic acid ethyl ester [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 1363 - 1365.

12
[ 425392-44-5 ]
[ 98-80-6 ]
[ 425392-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 2.0h;Reflux;	16.3. δ-Chloro^-phenyl-thiazole-i-carboxylic acid ethyl esterTo a solution of intermediate 16.2 (173 mg) in DME (1 mL) was added phenylboronic acid (67 mg), followed by [Pd(PPh3)4] (129 mg) and a solution Of K2CO3 (80.0 mg) in H2O (0.4 mL). The reaction mixture was heated at reflux for 2 h. The reaction mixture was allowed to cool down to RT and was extracted with EtOAc (3x). The combined org. layers were dried over MgSO4 and evaporated to dryness. CC (EtOAc/Hept 0:1 to EtOAc/Hept 1 :0) gave 93 mg of the desired product as yellowish oil. LC-MS: tR = 1.07 min; [M+H]+: 268.16.

References: [1]Patent: WO2010/122504,2010,A1 .Location in patent: Page/Page column 54.

13
[ 425392-44-5 ]
ethyl 2-(3-[2-[(3R)-3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl]ethynyl]phenyl)-5-[(1-methyl-1H-pyrazol-4-yl)amino]-1,3-thiazole-4-carboxylate [ No CAS ]

References: [1]Patent: WO2016/135163,2016,A1 .

14
[ 425392-44-5 ]
ethyl 2-(3-[2-[(3R)-3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl]ethynyl]phenyl)-5-[(oxetan-3-yl)amino]-1,3-thiazole-4-carboxylate [ No CAS ]

References: [1]Patent: WO2016/135163,2016,A1 .

15
potassium trifluoro(3-{2-[(3R)-3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl]ethynyl}phenyl)boranuide [ No CAS ]
[ 425392-44-5 ]
(R)-ethyl 5-chloro-2-(3-((3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)phenyl)thiazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In ethanol; water; at 85℃;Inert atmosphere; Sealed tube;	General procedure: A tube containing a solution of arylchloride/bromide (1 eq) and aryltrifluoroborate (1 eq) in Ethanol was purged with nitrogen before addition of Pd(OAc)2(0.06 eq), RuPhos (0.12 eq), and Sodium Carbonate (2 eq). The tube was sealed with a cap lined with a disposable Teflon septum was heated at 85 C for 12-20 hours. The reaction mixture was allowed to cool to room temperature and was either filtered thru celite and submitted directly to reverse phase HPLC purification or extracted with dichloromethane and a solution of saturated ammonium chloride before drying, evaporating and submitting to reverse phase purification or using in the subsequent step without purification.Similar to the procedure as described in General Procedure U, ethyl 2-bromo-5- chlorothiazole-4-carboxylate was reacted with potassium (ii)-trifluoro(3 -((3 -hydroxy- 1 -methyl - 2-oxopyrrolidin-3-yl)ethynyl)phenyl)borate to give the title compound (180 mg, 40%) as a light yellow solid. LC-MS (ES, m/z): 376 [M+H]+.

References: [1]Patent: WO2016/135163,2016,A1 .Location in patent: Paragraph 0198; 0210.

16
[ 425392-44-5 ]
(2-bromo-5-chlorothiazol-4-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19.2%	With sodium tetrahydroborate; ethanol; at 20℃; for 7.0h;Reflux;	2-Bromo-5-chlorothiazole-4-carboxylic acidEthyl ester (27.0 g, 100 mmol) was dissolved in absolute ethanol (250 mL)Sodium borohydride (11.3 g, 300 mmol) was added, stirred at room temperature for 4 hours, and then heated to reflux for 3 hours.The crude product was purified by column chromatography (ethyl acetate / petroleum ether (v / v) = 1/3) to give a pale yellow oil (4.4 g, 19.2%).

References: [1]Patent: CN104478866,2017,B .Location in patent: Paragraph 0311; 0313; 0314.

17
[ 425392-44-5 ]
ethyl 2,5-bis(4-isopropoxyphenyl)thiazole-4-carboxylate [ No CAS ]

References: [1]ChemMedChem,2020,vol. 15,p. 1691 - 1698.

18
[ 71597-85-8 ]
[ 425392-44-5 ]
ethyl 2,5-bis (4-hydroxyphenyl)thiazole-4-carboxylate [ No CAS ]

References: [1]ChemMedChem,2020,vol. 15,p. 1691 - 1698.

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

Related Functional Groups of
[ 425392-44-5 ]

Bromides

A394682 [1053655-63-2]

Methyl 2-bromo-5-chlorothiazole-4-carboxylate

Similarity: 0.98

A267040 [1027169-53-4]

2-Bromo-5-chlorothiazole-4-carboxylic acid

Similarity: 0.91

A241927 [100367-77-9]

Ethyl 2-bromothiazole-4-carboxylate

Similarity: 0.82

Chlorides

A394682 [1053655-63-2]

Methyl 2-bromo-5-chlorothiazole-4-carboxylate

Similarity: 0.98

A267040 [1027169-53-4]

2-Bromo-5-chlorothiazole-4-carboxylic acid

Similarity: 0.91

A102812 [425392-45-6]

Ethyl 5-chlorothiazole-4-carboxylate

Similarity: 0.84

A187427 [1784463-68-8]

Methyl 5-chlorothiazole-4-carboxylate

Similarity: 0.82

Esters

A394682 [1053655-63-2]

Methyl 2-bromo-5-chlorothiazole-4-carboxylate

Similarity: 0.98

A102812 [425392-45-6]

Ethyl 5-chlorothiazole-4-carboxylate

Similarity: 0.84

A241927 [100367-77-9]

Ethyl 2-bromothiazole-4-carboxylate

Similarity: 0.82

A187427 [1784463-68-8]

Methyl 5-chlorothiazole-4-carboxylate

Similarity: 0.82

Related Parent Nucleus of
[ 425392-44-5 ]

Thiazoles

A394682 [1053655-63-2]

Methyl 2-bromo-5-chlorothiazole-4-carboxylate

Similarity: 0.98

A267040 [1027169-53-4]

2-Bromo-5-chlorothiazole-4-carboxylic acid

Similarity: 0.91

A102812 [425392-45-6]

Ethyl 5-chlorothiazole-4-carboxylate

Similarity: 0.84

A241927 [100367-77-9]

Ethyl 2-bromothiazole-4-carboxylate

Similarity: 0.82

A187427 [1784463-68-8]

Methyl 5-chlorothiazole-4-carboxylate

Similarity: 0.82

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CAS No.: 425392-44-5

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