Methyl 2-bromo-5-isopropylthiazole-4-carboxylate

Base Information

• Chemical Name: Methyl 2-bromo-5-isopropylthiazole-4-carboxylate
• CAS No.: 81569-28-0
• Molecular Formula: C8H10BrNO2S
• Molecular Weight: 264.14000
• Hs Code.: 2934100090
• DSSTox Substance ID: DTXSID90432230
• Wikidata: Q72488600
• Mol file: 81569-28-0.mol

Synonyms:Methyl 2-bromo-5-isopropylthiazole-4-carboxylate;81569-28-0;Methyl 2-bromo-5-isopropyl-1,3-thiazole-4-carboxylate;Methyl 2-bromo-5-propan-2-yl-1,3-thiazole-4-carboxylate;methyl 2-bromo-5-(propan-2-yl)-1,3-thiazole-4-carboxylate;Methyl2-bromo-5-isopropylthiazole-4-carboxylate;SCHEMBL6284882;DTXSID90432230;AMY32173;MFCD09265507;AKOS015835057;PS-3836;CS-0159175;FT-0685394;EN300-1458199;J-521964

Chemical Property of Methyl 2-bromo-5-isopropylthiazole-4-carboxylate

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Boiling Point: 312.708oC at 760 mmHg
• Flash Point: 142.921oC
• PSA: 67.43000
• Density: 1.498g/cm3
• LogP: 2.81560
• Storage Temp.: 2-8°C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 262.96156
• Heavy Atom Count: 13
• Complexity: 201

Purity/Quality:

97% ^*data from raw suppliers

Methyl 2-bromo-5-isopropylthiazole-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(N=C(S1)Br)C(=O)OC

Technology Process of Methyl 2-bromo-5-isopropylthiazole-4-carboxylate

There total 1 articles about Methyl 2-bromo-5-isopropylthiazole-4-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

methyl 2-amino-5-isopropyl-1,3-thiazole-4-carboxylate (81569-25-7) → methyl 2-bromo-5-isopropyl-thiazole-4-carboxylate (81569-28-0)

Guidance literature:

With copper(I) bromide; isopentyl nitrite; In acetonitrile; at 80 ℃; for 3h;

Reference yield:

methyl 2-bromo-5-isopropyl-thiazole-4-carboxylate (81569-28-0) → methyl (2S,4R)-4-[({2-[(5S,8R,10R)-1-(9H-fluoren-9-yl)-5,8-diisopropyl-7-methyl-3,6,12-trioxo-2,11-dioxa-4,7-diazatridecan-10-yl]-5-isopropyl-1,3-thiazol-4-yl}carbonyl)amino]-2-methyl-5-phenyl-pentanoate

Guidance literature:

Multi-step reaction with 11 steps

1.1: lithium borohydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 12.5 h / 0 - 23 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 0.5 h / 0 - 23 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.2: 3 h / -78 - -50 °C / Inert atmosphere

4.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; toluene / 36 h / 0 - 23 °C / Inert atmosphere

5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 23 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 23 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 1 h / 23 °C / Inert atmosphere

8.1: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogen phosphate monohydrate / tetrahydrofuran; tert-butyl alcohol; water / 1 h / 23 °C / Inert atmosphere

9.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 0 °C / Inert atmosphere

9.2: 24 h / 0 - 23 °C / Inert atmosphere

10.1: dichloromethane / 2 h / 0 - 23 °C / Inert atmosphere

11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium chlorite; lithium borohydride; n-butyllithium; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 10.1: |Acyloin Condensation;

DOI:10.1021/jacs.7b12692

Reference yield:

methyl 2-bromo-5-isopropyl-thiazole-4-carboxylate (81569-28-0) → methyl (2S,4R)-4-[({2-[(1R,3R)-1-acetoxy-4-methyl-3-{methyl[(2S)-3-methyl-2-({[(2R)-1-methyl-pipe ridin-2-yl]carbonyl}amino)butanoyl]amino}pentyl]-5-isopropyl-1,3-thiazol-4-yl}carbonyl)amino]-2-methyl-5-phenylpentanoate

Guidance literature:

Multi-step reaction with 13 steps

1.1: lithium borohydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 12.5 h / 0 - 23 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 0.5 h / 0 - 23 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.2: 3 h / -78 - -50 °C / Inert atmosphere

4.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; toluene / 36 h / 0 - 23 °C / Inert atmosphere

5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 23 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 23 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 1 h / 23 °C / Inert atmosphere

8.1: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogen phosphate monohydrate / tetrahydrofuran; tert-butyl alcohol; water / 1 h / 23 °C / Inert atmosphere

9.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 0 °C / Inert atmosphere

9.2: 24 h / 0 - 23 °C / Inert atmosphere

10.1: dichloromethane / 2 h / 0 - 23 °C / Inert atmosphere

11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere

12.1: 2,2',2''-triaminotriethylamine / dichloromethane / 2 h / 0 - 23 °C / Inert atmosphere

13.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 24 h / 0 - 23 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium chlorite; lithium borohydride; n-butyllithium; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; 2,2',2''-triaminotriethylamine; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 10.1: |Acyloin Condensation;

DOI:10.1021/jacs.7b12692

upstream raw materials:

methyl 2-amino-5-isopropyl-1,3-thiazole-4-carboxylate