[ CAS No. 4175-78-4 ] {[proInfo.proName]}

Name: 4175-78-4|2,5-Dibromothiazole|97%
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SKU: A661115
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Quality Control of [ 4175-78-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 4175-78-4 ]

Product Details of [ 4175-78-4 ]

CAS No. :	4175-78-4	MDL No. :	MFCD00016891
Formula :	C₃HBr₂NS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XIBIQFJKUZZLLX-UHFFFAOYSA-N
M.W :	242.92	Pubchem ID :	312394
Synonyms :

Calculated chemistry of [ 4175-78-4 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	37.51
TPSA :	41.13 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) :	-5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	3.0
Log Po/w (WLOGP) :	2.67
Log Po/w (MLOGP) :	1.38
Log Po/w (SILICOS-IT) :	3.74
Consensus Log Po/w :	2.53

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.76
Solubility :	0.0418 mg/ml ; 0.000172 mol/l
Class :	Soluble
Log S (Ali) :	-3.53
Solubility :	0.072 mg/ml ; 0.000296 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.0
Solubility :	0.24 mg/ml ; 0.000989 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.73

Safety of [ 4175-78-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4175-78-4 ]

* 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 [ 4175-78-4 ]
Downstream synthetic route of [ 4175-78-4 ]

[ 4175-78-4 ] Synthesis Path-Upstream 1~6

1
[ 288-47-1 ]
[ 3034-53-5 ]
[ 4175-78-4 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1986, vol. 22, # 6, p. 663 - 666[2] Khimiya Geterotsiklicheskikh Soedinenii, 1986, vol. 22, # 6, p. 837 - 840

2
[ 4175-78-4 ]
[ 3034-55-7 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1986, vol. 22, # 6, p. 663 - 666[2] Khimiya Geterotsiklicheskikh Soedinenii, 1986, vol. 22, # 6, p. 837 - 840
[3] Journal of Organic Chemistry, 2006, vol. 71, # 10, p. 3754 - 3761

3
[ 3034-22-8 ]
[ 4175-78-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With copper(ll) bromide; isopentyl nitrite In acetonitrile at 60℃; for 4 h;	A solution of 2-amino-5-bromothiazole (1-21) (5.5 g, 30.72 mmol) in acetonitrile (50 mL) was treated with copper (II) bromide (3.43 g, 15.36 mmol) and isoamyl nitrite (4.9 mL, 36.87 mmol), and the resulting reaction mixture was heated at 60°C for 4 hours. The volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL) , followed by extraction with ethyl acetate (25 mL x 2), The combined organic layers were washed with brine (50 mL) , dried over anhydrous Na2S04 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (60-120 mesh) using 10percent EtOAc in hexanes to give the desired product 1-22 (5.05 g, 68percent) as a yellow liquid; LCMS : m/z 243.6 [M+2].
68%	With copper(ll) bromide; isopentyl nitrite In acetonitrile at 60℃; for 4 h;	Step I: 2,5-dibromothiazole (1-22) A solution of 2-amino-5-bromothiazole (1-21) (5.5 g, 30.72 mmol) in acetonitrile (50 mL) was treated with copper(II) bromide (3.43 g, 15.36 mmol) and isoamyl nitrite (4.9 mL, 36.87 mmol), and the resulting reaction mixture was heated at 60° C. for 4 hours. The volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL), followed by extraction with ethyl acetate (25 mL*2). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (60-120 mesh) using 10percent EtOAc in hexanes to give the desired product 1-22 (5.05 g, 68percent) as a yellow liquid; LCMS: m/z 243.6 [M⁺+2].

Reference： [1] Patent: WO2015/88045, 2015, A1, . Location in patent: Paragraph 0260
[2] Patent: US2017/8885, 2017, A1, . Location in patent: Paragraph 0672-0673
[3] Bulletin de la Societe Chimique de France, 1962, p. 2075 - 2078
[4] Journal of Organic Chemistry, 2017, vol. 82, # 11, p. 5947 - 5951

4
[ 288-47-1 ]
[ 4175-78-4 ]

Yield	Reaction Conditions	Operation in experiment
77%	With carbon tetrabromide; sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 3 h;	Compound thiazole (1 mmol, 84.9 mg)Carbon tetrabromide (2.1 mmol, 696.4 mg) was placed in a 10 mL round bottom flask.Added 5 mL of N,N-dimethylformamide and sodium tert-butoxide (4.0 mmol, 384.4 mg).Stir at room temperature for 3 hours,TLC monitored the endpoint of the reaction.The mixture was poured into water and extracted with dichloromethane. The organic phase was collected and dried. The dichloromethane was removed by rotary evaporation at low temperature to obtain a crude product.The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluent (volume ratio = 30:1).2,5-Dibromothiazole (colorless liquid, slow crystallisation at low temperature, 186.4 mg, yield 77percent) was obtained.

Reference： [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 6, p. 886 - 890
[2] Patent: CN107501023, 2017, A, . Location in patent: Paragraph 0059; 0060

5
[ 3034-53-5 ]
[ 4175-78-4 ]

Reference： [1] Synthesis, 2012, vol. 44, # 7, p. 1026 - 1029
[2] Journal of Organic Chemistry, 2017, vol. 82, # 11, p. 5947 - 5951
[3] Journal of Organic Chemistry, 2006, vol. 71, # 10, p. 3754 - 3761
[4] Helvetica Chimica Acta, 1954, vol. 37, p. 2057,2064
[5] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 4, p. 845 - 849

6
[ 288-47-1 ]
[ 3034-53-5 ]
[ 4175-78-4 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1986, vol. 22, # 6, p. 663 - 666[2] Khimiya Geterotsiklicheskikh Soedinenii, 1986, vol. 22, # 6, p. 837 - 840

[ 4175-78-4 ] Synthesis Path-Downstream 1~88

1
[ 3034-22-8 ]
[ 4175-78-4 ]

Yield	Reaction Conditions	Operation in experiment
68%	With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 60℃; for 4h;	A solution of 2-amino-5-bromothiazole (1-21) (5.5 g, 30.72 mmol) in acetonitrile (50 mL) was treated with copper (II) bromide (3.43 g, 15.36 mmol) and isoamyl nitrite (4.9 mL, 36.87 mmol), and the resulting reaction mixture was heated at 60C for 4 hours. The volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL) , followed by extraction with ethyl acetate (25 mL x 2), The combined organic layers were washed with brine (50 mL) , dried over anhydrous Na2S04 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (60-120 mesh) using 10% EtOAc in hexanes to give the desired product 1-22 (5.05 g, 68%) as a yellow liquid; LCMS : m/z 243.6 [M+2].
68%	With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 60℃; for 4h;	Step I: 2,5-dibromothiazole (1-22) A solution of 2-amino-5-bromothiazole (1-21) (5.5 g, 30.72 mmol) in acetonitrile (50 mL) was treated with copper(II) bromide (3.43 g, 15.36 mmol) and isoamyl nitrite (4.9 mL, 36.87 mmol), and the resulting reaction mixture was heated at 60 C. for 4 hours. The volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL), followed by extraction with ethyl acetate (25 mL*2). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (60-120 mesh) using 10% EtOAc in hexanes to give the desired product 1-22 (5.05 g, 68%) as a yellow liquid; LCMS: m/z 243.6 [M++2].

Reference： [1]Patent: WO2015/88045,2015,A1 .Location in patent: Paragraph 0260
[2]Patent: US2017/8885,2017,A1 .Location in patent: Paragraph 0672-0673
[3]Bulletin de la Societe Chimique de France,1962,p. 2075 - 2078
[4]Journal of Organic Chemistry,2017,vol. 82,p. 5947 - 5951

2
[ 288-47-1 ]
[ 3034-53-5 ]
[ 4175-78-4 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1986,vol. 22,p. 663 - 666
Khimiya Geterotsiklicheskikh Soedinenii,1986,vol. 22,p. 837 - 840

3
[ 4175-78-4 ]
[ 6165-68-0 ]
[ 54987-01-8 ]

Reference： [1]Heterocycles,1990,vol. 30,p. 645 - 658

4
[ 4175-78-4 ]
[ 116886-71-6 ]
[ 128141-00-4 ]

Reference： [1]Heterocycles,1990,vol. 30,p. 645 - 658

5
[ 4175-78-4 ]
[ 119405-65-1 ]
[ 128140-99-8 ]

Reference： [1]Heterocycles,1990,vol. 30,p. 645 - 658

6
[ 4175-78-4 ]
[ 108306-54-3 ]
[ 111185-09-2 ]
[ 111185-11-6 ]

Reference： [1]Synthesis,1987,p. 185 - 186

7
[ 4175-78-4 ]
[ 108306-54-3 ]
[ 111185-07-0 ]

Reference： [1]Synthesis,1987,p. 185 - 186

8
[ 4175-78-4 ]
[ 108306-58-7 ]
[ 111185-09-2 ]

Reference： [1]Synthesis,1987,p. 185 - 186

10
[ 4175-78-4 ]
[ 3034-55-7 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1986,vol. 22,p. 663 - 666
Khimiya Geterotsiklicheskikh Soedinenii,1986,vol. 22,p. 837 - 840
[2]Journal of Organic Chemistry,2006,vol. 71,p. 3754 - 3761

11
[ 3034-52-4 ]
[ 4175-78-4 ]
5-bromo-2'-chloro-2,5'-bithiazole [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 3754 - 3761

12
[ 903886-71-5 ]
[ 4175-78-4 ]
5-(5-bromo-thiazol-2-yloxy)-2-isopropoxy-pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3770 - 3773

13
[ 4175-78-4 ]
[ 99-89-8 ]
[ 903886-70-4 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3770 - 3773

14
[ 4175-78-4 ]
[ 637-89-8 ]
4-(5-bromothiazol-2-ylsulfanyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 0.333333h;	EXAMPLE 103; N-(3-{2-[(4-isopropoxyphenyl)thio]-1,3-thiazol-5-yl}-1-methylprop-2-ynyl)acetamide; EXAMPLE 103A; 4-(5-Bromo-thiazol-2-ylsulfanyl)-phenol; A solution of 4-mercaptophenol (300 mg, 2.38 mmol) and <strong>[4175-78-4]2,5-dibromothiazole</strong> (635 mg, 2.61 mmol) in DMF (5 mL) was treated with K2CO3 (290 mg, 2.1 mmol) and the resulting mixture was heated at 90 C. for 20 min. The reaction was cooled to 25 C., diluted with water (20 mL) and extracted with 1:1 EtOAc/Et2O (100 mL). The organic layer was washed with water (3×25 mL), and brine (25 mL), dried (Na2SO4), filtered, and evaporated. The crude product was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 25% EtOAc in hexanes to provide 586 mg (85%) of Example 103A as a white solid.

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3770 - 3773
[2]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 44

15
[ 4175-78-4 ]
[ 7495-77-4 ]
[ 903886-65-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In dimethyl sulfoxide; at 95℃;	EXAMPLE 92; N-(3-{2-[3-(cyclohexylmethoxy)-5-methylphenoxy]-1,3-thiazol-5-yl}-1-methylprop-2-ynyl)acetamide; EXAMPLE 92A; 4-Bromo-2-(4-isopropoxy-phenoxy)-thiazole; To a solution of 4-Isopropoxy-phenol (CASNo. 7495-774, 1.62 g, 10.64 mmole) in DMSO (25 mL) was added in turn, potassium carbonate (3 g, 21.7 mmole) and <strong>[4175-78-4]2,5-dibromothiazole</strong> (2.64 g, 11.7 mmole). The reaction mixture was heated at 95 C. overnight. The reaction mixture was cooled down, added water and extracted with ethyl acetate (2×40 mL). The reaction mixture was diluted with ethyl acetate (100 mL), added water (100 mL) and separated. The organic phase was washed with water (100 mL×2) and brine, dried over magnesium sulfate and evaporated in vacuum. The product was purified on silica column using a gradient of 3-10% ethyl acetate in hexane and yielded 3.11 g (99%) of white solid. 1H NMR (300 MHz, CHLOROFORM-D) delta ppm 7.07-7.23 (m, 3H) 6.81-6.96 (m, 2H) 4.40-4.62 (heptet, J=6.25 Hz, 1H) 1.34 (d, J=6.25 Hz, 4H), MS (ESI) M/Z 315 (M+1)+.

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 40
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2498 - 2503
[3]Journal of Medicinal Chemistry,2006,vol. 49,p. 3770 - 3773

16
[ 4175-78-4 ]
[ 70551-46-1 ]
[ 904961-99-5 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3770 - 3773
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

17
[ 4175-78-4 ]
[ 54840-15-2 ]
[ 903886-67-9 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3770 - 3773

18
[ 4175-78-4 ]
[ 79887-17-5 ]
2,5-bis[(4-hexyloxyphenyl)ethynyl]thiazole [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 363,p. 77 - 84

19
[ 4175-78-4 ]
[ 79887-19-7 ]
2,5-bis[(4-octyloxyphenyl)ethynyl]thiazole [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 363,p. 77 - 84

20
[ 4175-78-4 ]
[ 115573-46-1 ]
2,5-bis[(4-decyloxyphenyl)ethynyl]thiazole [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 363,p. 77 - 84

21
[ 4175-78-4 ]
[ 121051-42-1 ]
2,5-bis[(4-dodecyloxyphenyl)ethynyl]thiazole [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 363,p. 77 - 84

22
[ 4175-78-4 ]
[ 160094-57-5 ]
2,5-bis[(4-tetradecyloxyphenyl)ethynyl]thiazole [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 363,p. 77 - 84

23
[ 4175-78-4 ]
1-[(S)-2-methylbutyloxy]-4-ethynylbenzene [ No CAS ]
2,5-bis[((S)-4-(3-methyl)butyloxyphenyl)ethynyl]thiazole [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 363,p. 77 - 84

24
[ 94-71-3 ]
[ 4175-78-4 ]
5-bromo-2-(2-ethoxy-phenoxy)-thiazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

25
[ 120-47-8 ]
[ 4175-78-4 ]
[ 916796-13-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

26
[ 4175-78-4 ]
[ 827-99-6 ]
5-bromo-2-(3-trifluoromethoxy-phenoxy)-thiazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

27
[ 4175-78-4 ]
[ 713-68-8 ]
5-bromo-2-(3-phenoxy-phenoxy)-thiazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

28
[ 4175-78-4 ]
[ 4812-20-8 ]
5-bromo-2-(2-isopropoxy-phenoxy)-thiazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

29
[ 4175-78-4 ]
[ 4167-74-2 ]
[ 916795-99-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

30
[ 4175-78-4 ]
[ 831-82-3 ]
5-bromo-2-(4-phenoxy-phenoxy)-thiazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

31
[ 4175-78-4 ]
[ 7781-98-8 ]
[ 904961-84-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

32
[ 4175-78-4 ]
[ 23576-79-6 ]
[4-(5-bromo-thiazol-2-yloxy)-phenyl]-isopropyl-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

33
[ 4175-78-4 ]
[ 90-05-1 ]
5-bromo-2-(2-methoxy-phenoxy)-thiazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

34
[ 4175-78-4 ]
[ 123-31-9 ]
[ 904961-21-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate; In N,N-dimethyl-formamide; at 180℃; for 0.166667h;Microwave irradiation;Product distribution / selectivity;	EXAMPLE 11; N-(3-{2-[4-(cyclopentylmethoxy)phenoxy]-1,3-thiazol-5-yl}-1-methylprop-2-yl)acetamide; EXAMPLE 11A; 4-[(5-bromo-1,3-thiazol-2-yl)oxy]phenol; A mixture of hydroquinone (440 mg, 4.0 mmol), <strong>[4175-78-4]2,5-dibromothiazole</strong> (486 mg, 2.0 mmol) and potassium carbonate (276 mg, 2.0 mmol) in DMF (4 mL) was heated in a microwave oven at 180 C. for 10 minutes. The mixture was partitioned between ethyl acetate and saturated NaHCO3 (30 mL, 1:1). The organic phase was washed with brine (×3), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel column with ethyl acetate/hexane (1/2) to provide 408 mg titled compound (yield 76%).
63%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 3h;Product distribution / selectivity;	EXAMPLE 81; N-(3-{2-[4-(allyloxy)phenoxy]-1,3-thiazol-5-yl}-1-methylprop-2-ynyl)acetamide; EXAMPLE 81A; 4-(5-Bromo-thiazol-2-yloxy)-phenol; A solution of <strong>[4175-78-4]2,5-dibromothiazole</strong> (3 g, 12.35 mmol), and hydroquinone (2.04 g, 18.53 mmol) in DMF (30mL) was treated with potassium carbonate (1.71 g, 12.35 mmol) and the mixture was heated at 130 C. for 3 h. The reaction was cooled to 25 C., poured into water (200 mL) and extracted with diethyl ether (3×150 mL). The combined organic layers were washed with water (3×150 mL) and brine (150 mL), dried over sodium sulfate and concentrated on a rotary evaporator. The crude concentrate (3.2 g) was purified by flash chromatography on silica gel eluting with a solvent gradient from 1% to 5% methanol in chloroform to provide 2.1 g (63%) of Example 81 a as a tan solid. 1H NMR (300 MHz, DMSO-D6) delta ppm 6.82 (d, J=8.82 Hz, 2H) 7.19 (d, J=8.82 Hz, 2H) 7.40 (s, 1H) 9.70 (s, 1H); MS (ESI) m/z 273.7 (M+H)+.

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 24
[2]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 37
[3]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

35
[ 4175-78-4 ]
[ 108-46-3 ]
[ 904961-08-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 2h;	EXAMPLE 1; N-(3-{2-[3-(cyclohexylmethoxy)phenoxy]-1,3-thiazol-5-yl}-1-methylprop-2-ynyl)acetamide; EXAMPLE 1A; A solution of <strong>[4175-78-4]2,5-dibromothiazole</strong> (5 g, 20.58 mmol) and resorcinol (4.53 g, 41.16 mmol) in DMF (100 mL) was treated with potassium carbonate (2.86g, 20.58 mmol) and the mixture was heated at 130 C. for 2 h. The reaction was cooled to 25 C., poured into water (400 mL) and extracted with diethyl ether (3×250 mL). The combined organic layers were washed with water (3×150 mL) and brine (150 mL), dried over sodium sulfate and concentrated on a rotary evaporator. The crude concentrate (6.4 g) was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 25% ethyl acetate in hexanes to provide 3.6 g (64%) of Example 1a as awhite solid. 1H NMR (300 MHz, DMSO-D6) delta ppm 6.67-6.88 (m, 2H) 7.28 (t, J=8.27 Hz, 1H) 7.51 (s, 1H) 9.90 (s, 1H); MS (ESI) m/z 273.6(M+H)+.

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 20
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

36
[ 4175-78-4 ]
[ 108-95-2 ]
5-bromo-2-phenoxy-thiazol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6078 - 6081

37
[ 4175-78-4 ]
[ 167683-93-4 ]
[ 936247-37-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1961 - 1965

38
[ 4175-78-4 ]
[ 17332-11-5 ]
[ 936247-39-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1961 - 1965

39
[ 4175-78-4 ]
[ 5307-05-1 ]
[ 936247-40-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1961 - 1965

40
[ 4175-78-4 ]
[ 1568-70-3 ]
[ 936247-42-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1961 - 1965

41
[ 672-13-9 ]
[ 4175-78-4 ]
[ 936247-41-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1961 - 1965

42
[ 4175-78-4 ]
[ 18113-03-6 ]
[ 936247-38-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In N,N-dimethyl-formamide; at 105℃; for 3h;	Step 1 Preparation of Compound a24 (0440) 2,5-Dibromo-thiazole (8.6g, 35mmol) and Compound a23 (6.0g, 38mmol) were dissolved in DMF (90mL), and potassium carbonate (9.8g, 71mmol) was added, and the mixture was stirred at 105 C for 3 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give compound a24 (12g, 100% yield). 1H NMR (CDCl3) delta: 3.81 (s, 3H), 6.84 (dd, J = 8.9, 3.0 Hz, 1H), 7.00 (d, J = 3.0 Hz, 1H), 7.11 (s, 1H), 7.23 (d, J = 8.9 Hz, 1H).
94%	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 6h;	Step 1 Preparation of Compound 14 (0533) To DMF solution of the compound 12 (7.63 g, 31.4 mmol) and compound 13 (5.98 g, 37.7 mmol), potassium carbonate (5.21 g, 37.7 mmol) was added. The mixture was stirred at 120 C. for 6 hours. Water was added to the reaction mixture, the mixture was extracted with diethylether. The organic layer was washed with saturated brine, dried over magnesium sulfate. The solvent was condensed under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate) to afford Compound 14 (9.42 g, yield 94%). (0534) 1H-NMR (CDCl3) delta: 7.23 (d, J=8.9 Hz, 1H), 7.11 (s, 1H), 7.00 (d, J=3.0 Hz, 1H), 6.84 (dd, J=8.9, 3.0 Hz, 1H), 3.81 (s, 3H).

Reference： [1]Patent: EP3059225,2016,A1 .Location in patent: Paragraph 0440
[2]Patent: US2015/246938,2015,A1 .Location in patent: Paragraph 0533-0534
[3]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1961 - 1965

43
[ 4175-78-4 ]
[ 106-51-4 ]
[ 904961-21-3 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1078 - 1082

44
[ 201811-58-7 ]
[ 4175-78-4 ]
[ 929118-53-6 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1078 - 1082

45
[ 4175-78-4 ]
[ 5188-07-8 ]
[ 956293-02-0 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 4099 - 4102

46
[ 4175-78-4 ]
[ 141449-85-6 ]
[ 848593-79-3 ]

Yield	Reaction Conditions	Operation in experiment
69%	With N-ethyl-N,N-diisopropylamine; at 110℃; for 2h;	EXAMPLE 44A 5-(5-Bromo-thiazol-2-yl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic Acid Tert-Butyl Ester To the product of Example 6C (1.0 g, 4.2 mmol) in N,N-diisopropylethylamine (1.5 mL, 8.4 mmol) was added <strong>[4175-78-4]2,5-dibromothiazole</strong> (Aldrich, 0.89 g, 4.2 mmol). This mixture was warmed to 110 C. and stirred for 2 h. The reaction mixture was cooled to ambient temperature, concentrated under reduced pressure, and purified by column chromatography (SiO2, 20-40% ethyl acetate-hexanes gradient) to afford 1.1 g of the title compound (2.9 mmol, 69% yield). 1H NMR (CDCl3, 300 MHz) delta 1.46 (s, 9H), 2.97-3.09 (m, 2H), 3.21-3.41 (m, 4H), 3.60-3.71 (m, 4H), 7.09 (s, 1H); MS (DCI/NH3) m/z 376 (M+H)+.
69%	With N-ethyl-N,N-diisopropylamine; at 110℃; for 2h;	Example 260A 5-(5-Bromo-thiazol-2-yl)-hexa hydro-pyrrolo[3,4-c]pyrrole-2-carboxylic Acid tert-butyl Ester A solution of Example 6C (1.0 g, 4.2 mmol) in N,N-diisopropylethylamine (1.5 mL, 8.4 mmol) was treated with <strong>[4175-78-4]2,5-dibromothiazole</strong> (0.89 g, 4.2 mmol, Aldrich). This mixture was warmed to 110 C. and stirred for 2 hours. The reaction mixture was cooled to ambient temperature, concentrated under reduced pressure, and purified by column chromatography (SiO2, 20-40% ethyl acetate/hexanes gradient) to afford 1.1 g of the title compound (2.9 mmol, 69% yield). 1H NMR (CDCl3, 300 MHz) delta 1.46 (s, 9H), 2.97-3.09 (m, 2H), 3.21-3.41 (m, 4H), 3.60-3.71 (m, 4H), 7.09 (s, 1H); MS (DCl/NH3) m/z 376 (M+H+).

Reference： [1]Patent: US2005/65178,2005,A1 .Location in patent: Page/Page column 40
[2]Patent: US2005/101602,2005,A1 .Location in patent: Page/Page column 69

47
[ 4175-78-4 ]
[ 14396-90-8 ]
[ 484673-76-9 ]

Yield	Reaction Conditions	Operation in experiment
55%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 70℃; for 5h;	Step 2: Only degassed solvents were used under anhydrous conditions. A mixture of 312a (1. 5 eq), 2, 5-dibromothiazole (1 eq), bis (triphenylphosphine)- palladium (II) chloride (3%), and Cul (3%) in 2: 1 THF : TEA was stirred at 70C for 5 h, cooled to ambient temperature, filtered through a pad of silica gel, concentrated, and purified by silica gel chromatography (eluting with 3: 1: 1 hexanes: EtOAc: DCM) to afford 312b (55%).

Reference： [1]Patent: WO2004/96822,2004,A2 .Location in patent: Page 260; 261

48
[ 4175-78-4 ]
[ 17997-47-6 ]
[ 862500-43-4 ]

Yield	Reaction Conditions	Operation in experiment
14%	bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); at 140℃; for 0.05h;Microwave irradiation;	Reference example 3; 2- .-pyridine; A microwave vial (20 mL) was charged with a solution, in DMF (20 mL), of 2- tributylstannanyl-pyridine (Aldrich ; 80%, 2.19g, 4.76 mmol), 2, 5-dibromo-thiazole (Aldrich; 2.0 g, 8.23 mmol) and dichlorobis (triphenylphosphine) palladium (II) (395 mg, 0.56 mmol). The resulting mixture was microwave irradiated for 3 minutes at 140 C then diluted with methanol (20 mL) and applied to an SCX-2 cartridge (70 g; sulphonic acid ion-exchange resin). Elution, first with methanol, allowed removal of DMF and excess stannane, and further elution with 2 M ammonia in methanol afforded the enriched pyridyl- thiazole product. Subsequent flash silica-gel chromatography, gradient eluting from cyclohexane to 20% diethylether in cyclohexane, afforded 2- (5-bromo-thiazol-2-yl)- pvridine (161 mg, 14%) as an amber oil that solidified on standing. 1H NMR (CDCl3) : 8. 58 (d, 1H), 8.10 (d, 1H), 7.79 (dt, 1H), 7.78 (s, 1H), 7. 33 (ddd, 1H).

Reference： [1]Patent: WO2005/75469,2005,A1 .Location in patent: Page/Page column 32

49
[ 4175-78-4 ]
[ 541-41-3 ]
ethyl 2,4-dibromo-1,3-thiazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; at -70 - 0℃; for 0.5h;	A solution of 14 ml of 1. 6 N n-butylithium in hexane was added slowly to a solution of diisopropylamine (3. 1 ml, 22 mmol) in 80 ml THF cooled in a dry ice/acetone bath under an inert atmosphere. The solution was warmed to 0 C and RE-COOLED TO-70 C. A solution of 2, 5-dibromothiazole in 20 ml THF was added and the mixture was stirred for 30 min before adding ethyl chloroformate (2.1 ml, 22 MMOL). After warming to room temperature, the mixture was quenched with aqueous NAHC03 and diluted with EtOAc. The EtOAc was separated and washed with water and brine. Drying (MGS04) and removal of solvent gave an oil that was purified by chromatography (1 : l hexanes-DCM followed by gradient elution to 100% DCM) to give 4.5 g of product as an oil that slowly solidified. MS (ES . : 316 (M+H) 1H NMR (CDCL3) No.: 1.4 (t, 3H); 4.4 (q, 2H).

Reference： [1]Patent: WO2005/26149,2005,A1 .Location in patent: Page/Page column 123-124

50
[ 95-65-8 ]
[ 4175-78-4 ]
C₁₁H₁₀BrNOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With MP-carbonate; triethylamine; at 150℃; for 0.333333h;Microwave irradiation;	EXAMPLE 113; N-{3-[2-(3,4-dimethylphenoxy)-1,3-thiazol-5-yl]-1-methylprop-2-ynyl}acetamide; A Smith Process vial (0.5-2 ml) was charged with a stir bar. To the vessel were added dibromothiazole(36 mg, 0.15 mmol) and 3,4-dimethylphenol (0.16 mmol). MP-Carbonate (0.45 mmol, 3 mmol/g loading) was added to above solution. The reaction vessel was sealed and heated in microwave to 150 C. for 1200 s. After cooling, the reaction vessel was uncapped. Without further work-up, triethylamine (63 mul, 0.45 mmol) and alkyne (18 mg, 0.16 mmol) were added to the resulting mixture followed by PdCl2(PPh3)2 (5.3 mg, 0.0075 mmol) and CuI (1 mg, 0.0045 mmol). The resulting reaction mixture was capped and heated in microwave to 150 C. for another 1200 s. After cooling, the vessel was again uncapped and filtered through a small plug of silica gel. The filtrate was collected and dried. HPLC purification gave the desired products. 1H NMR delta; 1.32 (d, 3H, J=7.1 Hz), 1.81 (s, 3H), 2.23 (s, 3H), 2.24 (s, 3H), 4.81 (m, 1H),7.08 (dd, 1H, J=8.2, 2.5 Hz) 7.16 (d, 1H, J=2.5 Hz), 7.32 (d, 1H, J=8.2 Hz), 7.47 (s, 1H), 8.37 (d, 1H, 7.8 Hz); MS (ESI) m/z 314.9 (M+H)

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 46

51
[ 4175-78-4 ]
[ 135-19-3 ]
[ 904962-67-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate; In dimethyl sulfoxide; at 130℃; for 0.5h;Microwave irradiation;	EXAMPLE 121; N-{1-methyl-3-[2-(2-naphthyloxy)-1,3-thiazol-5-yl]prop-2-ynyl}acetamide; EXAMPLE 121A; 5-Bromo-2-(naphthalene-2-yloxy)-thiazole; 2,5-Dibromothiazole (0.250 g, 1.03 mmoL) was dissolved in anhydrous DMSO (4.0 mL). This was treated with 2-naphthol (0.156 g, 1.08 mmoL) followed by potassium carbonate (0.144 g, 1.03 mmoL). The solution was then heated in the microwave at 130 C. for 30 minutes. The contents of the reaction were then poured into brine (25 mL) and extracted with CH2Cl2 (3×25 mL). The combined extracts were washed with brine (5×25 mL) then dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 1 EtOAc/19 hexanes) to afford the title compound (0.246 g, 79%). MS (CI) m/e 305.9(M+H); 1H NMR (300 MHz, CDCl3) delta ppm 7.19 (s, 1H) 7.37 (dd, J=8.82, 2.21 Hz, 1H) 7.42-7.54 (m, 2H) 7.71 (d, J=2.21 Hz, 1H) 7.75-8.02 (m, 3H)

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 48

52
[ 95-87-4 ]
[ 4175-78-4 ]
C₁₁H₁₀BrNOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With MP-carbonate; at 150℃; for 0.333333h;Microwave irradiation;	EXAMPLE 119; N-{3-[2-(2,5-dimethylphenoxy)-1,3-thiazol-5-yl]-1-methylprop-2-ynyl}acetamide; A Smith Process vial (0.5-2 ml) was charged with a stir bar. To the vessel were added dibromothiazole(36 mg, 0.15 mmol) and 2,5-dimethylphenol (0.16 mmol). MP-Carbonate (0.45 mmol, 3 mmol/g loading) was added to above solution. The reaction vessel was sealed and heated in microwave to 150 C. for 1200 s. After cooling, the reaction vessel was uncapped. Without further work-up, triethylamine (63 mul, 0.45 mmol ) and Example 5B (18 mg, 0.16 mmol) were added to the resulting mixture followed by PdCl2(PPh3)2 (5.3 mg, 0.0075 mmol) and CuI (1 mg, 0.0045 mmol). The resulting reaction mixture was capped and heated in microwave to 150 C. for another 1200 s. After cooling, the vessel was again uncapped and filtered through a small plug of silica gel. The filtrate was collected and dried. HPLC purification gave the desired products. 1H NMR delta; 1.32 (d, 3H, J=7.2 Hz), 1.81 (s, 3H), 2.13 (s, 3H), 2.29 (s, 3H), 4.81 (m, 1H),7.08 (d, 1H, J=7.5 Hz) 7.12 (s, 1H), 7.24 (d, 1H, J=7.5 Hz), 7.45 (s, 1H), 8.37 (d, 1H, 7.8 Hz); MS (ESI) m/z 314.9 (M+H).

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 47

53
[ 4175-78-4 ]
[ 123-08-0 ]
[ 904961-29-1 ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 4h;	EXAMPLE 16; N-(3-{2-[4-(1-hydroxy-3-methylbutyl)phenoxy]-1,3-thiazol-5-yl}-1-methylprop-2-ynyl)acetamide; EXAMPLE 16A; 4-(5-Bromo-thiazol-2-yloxy)-benzaldehyde; A mixture of <strong>[4175-78-4]2,5-dibromothiazole</strong> (3 g, 12.4 mmol), 4-hydroxybenzaldehyde (1.73 g, 14.2 mmol) and potassium carbonate (1.71 g, 12.4 mmol) in DMF (25 mL) was heated in an oil bath at 120 C. for 4 hours. The reaction was cooled to 25 C., poured into water (150 mL) and extracted with 1:1 ethyl acetate/ether (200 mL). The organic layer was washed with water (4×100 mL) and brine (2×100 mL), dried (Na2SO4), filtered and evaporated to provide 3.6 g of a residual pale orange oil. The residue was purified by flash chromatography on silica gel eluting with a solvent gradient from 3% to 14% ethyl acetate in hexanes to provide 2 g (57%) of Example 16A as a white solid. 1H NMR (300 MHz, DMSO-D6) delta ppm 7.53 (s, 1H) 7.58 (d, J=8.46 Hz, 2H) 8.03 (d, J=8.82 Hz, 2H) 10.01 (s, 1H); MS (DCI) m/z 286 (M+H)+.

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 25

54
[ 504-15-4 ]
[ 4175-78-4 ]
[ 904962-30-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 2h;	EXAMPLE 91; N-(3-{2-[3-(cyclohexylmethoxy)-5-methylphenoxy]-1,3-thiazol-5-yl}-1-methylprop-2-ynyl)acetamide; EXAMPLE 91A; 3-[(5-bromo-1,3-thiazol-2-yl)oxy]-5-methylphenol; A solution of <strong>[4175-78-4]2,5-dibromothiazole</strong> (200 mg, 0.82 mmol), and 5-methyl-benzene-1,3-diol (204 mg, 1.64 mmol) in DMF (8 mL) was treated with potassium carbonate (115 g, 0.82 mmol) and the mixture was heated at 130 C. for 2 h. The reaction was cooled to 25 C., poured into water (30 mL) and extracted with diethyl ether (3×35mL). The combined organic layers were washed with water (3×25 mL) and brine (25 mL), dried over sodium sulfate and concentrated on a rotary evaporator. The crude concentrate (350 mg) was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 25% ethyl acetate in hexanes to provide 191 mg (81%) of Example 91a as a white solid. 1H NMR (300 MHz, DMSO-D6) delta ppm 2.24 (s, 3H) 6.01 (s, 1H) 6.41-6.64 (m, 2H) 7.44 (s, 1H) 9.01 (s, 1H); MS (ESI) m/z 283.8 (M+H)+.

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 40

55
[ 4175-78-4 ]
[ 98-67-9 ]
[ 904962-01-2 ]

Yield	Reaction Conditions	Operation in experiment
74%		EXAMPLE 69; N-{3-[2-(4-[isopropyl(methyl)amino]sulfonyl}phenoxy)-1,3-thiazol-5-yl]-1-methylprop-2-ynyl}acetamide; EXAMPLE 69A; 4-(5-bromo-thiazol-2-yloxy)-benzenesulfonic acid; 4-Hydroxybenzenesulfonic acid (0.543 g, 2.03 mmoL, 65% w/w in H2O), <strong>[4175-78-4]2,5-dibromothiazole</strong> (0.443 g, 1.82 mmoL), and potassium carbonate (0.730 g, 5.29 mmoL) were dissolved in DMF (2 mL). The mixture was then heated in the microwave at 160 C. for 10 min. The reaction was cooled and the reaction filtered. The filtrate was acidified with 4N HCl in dioxane (2 mL) and filtered again. The filtrate was concentrated in vacuo to provide the title compound (0.453 g, 74%). MS (ESI) m/e 335.7 (M+H); 1H NMR (300 MHz, DMSO-d6) delta ppm 7.45 (s, 1H) 7.40 (d, J=8.46 Hz, 2H) 6.66 (d, J=8.46 Hz, 2H).

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 35

56
[ 4175-78-4 ]
[ 499-75-2 ]
C₁₃H₁₄BrNOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With MP-carbonate; at 150℃; for 0.333333h;Microwave irradiation;	EXAMPLE 120; N-{3-[2-(5-isopropyl-2-methylphenoxy)-1,3-thiazol-5-yl]-1-methylprop-2-ynyl}acetamide; A Smith Process vial (0.5-2 ml) was charged with a stir bar. To the vessel were added dibromothiazole(36 mg, 0.15 mmol) and 3-(2-methyl-ethyl)-6-methylphenol (0.16 mmol). MP-Carbonate (0.45 mmol, 3 mmol/g loading) was added to above solution. The reaction vessel was sealed and heated in microwave to 150 C. for 1200 s. After cooling, the reaction vessel was uncapped. Without further work-up, triethylamine (63 mul, 0.45 mmol) and Example 5B (18 mg, 0.16 mmol) were added to the resulting mixture followed by PdCl2(PPh3)2 (5.3 mg, 0.0075 mmol) and CuI (1 mg, 0.0045 mmol). The resulting reaction mixture was capped and heated in microwave to 150 C. for another 1200 s. After cooling, the vessel was again uncapped and filtered through a small plug of silica gel. The filtrate was collected and dried. HPLC purification gave the desired products. 1H NMR delta; 1.18 (d, 6H, J=6.0 Hz), 1.32 (d, 3H, J=7.2 Hz), 1.81 (s, 3H), 2.13 (s, 3H), 4.81 (m, 1H), 7.16 (d, 1H, J=7.5 Hz) 7.16 (s, 1H), 7.28 (d, 1H, J=7.5 Hz), 7.45 (s, 1H), 8.37 (d, 1H, 7.8 Hz); MS (ESI) m/z 343.0 (M+H)

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 47-48

57
[ 110-85-0 ]
[ 4175-78-4 ]
[ 223514-48-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine; In tetrahydrofuran; at 160℃; for 0.166667h;Microwave irradiation;	a) l-(5-Bromo-thiazol-2-yl)-piperazine; A mixture of 2.06 mmol <strong>[4175-78-4]2,5-dibromothiazole</strong>, 6.17 mmol piperazine and 6.17 mmol triethylamine in 6 ml tetrahydrofuran in a sealed tube was heated at 1600C for 10 min under microwave irradiation. The reaction mixture was concentrated and the residue was purified by chromatography (SiO2, methanol/dichloromethane) to afford the title compound as a white crystalline solid (yield 94%). MS (m/e): 250.0 ({81Br}M+H+, 100%), 248.0 ({79Br}M+H+, 76%).
85%	In butan-1-ol; at 117℃; for 3h;	A solution of 2,5-Dibromo- thiazole (1.0 g, 4.1 mmol), piperazine ( 0.71 g, 8.2 mmol) in BuOH (5.0 mL) was stirred at 117 0C for 3 hrs. Remove solvent and extracted with 30% IPA in DCM, dry with sodium sulfate, and concentrated in vacuo to give the title product (1.1 g, 85%) as a brown solid. ESIMS m/z 247 (M + H+).
		Synthesis of 1-(5-bromothiazol-2-yl)piperazine 1-(5-Bromothiazol-2-yl)piperazine was obtained by the reaction of <strong>[4175-78-4]2,5-dibromothiazole</strong> with piperazine according to the conditions described above Precursor BBB1.

Reference： [1]Patent: WO2006/72436,2006,A1 .Location in patent: Page/Page column 33
[2]Patent: WO2009/120789,2009,A1 .Location in patent: Page/Page column 124
[3]Patent: US2007/112011,2007,A1

58
[ 4175-78-4 ]
[ 5060-82-2 ]
5-Bromo-2-(7-methoxy-naphthalene-2-yloxy)-thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium carbonate; In N,N-dimethyl-formamide; at 160℃; for 0.25h;Microwave irradiation;	EXAMPLE 100; N-(3-{2-[(7-methoxy-2-naphthyl)oxy]-1,3-thiazol-5-yl}-1-methylprop-2-ynyl)acetamide; EXAMPLE 100A; 5-Bromo-2-(7-methoxy-naphthalene-2-yloxy)-thiazole; 2,5-Dibromothiazole (0.610 g, 2.51 mmoL) was dissolved in anhydrous DMF (2.0 mL). This was treated with 7-methoxy-2-naphthol (0.536 g, 3.08 mmoL) followed by potassium carbonate (0.265 g, 1.92 mmoL). The solution was then heated in the microwave at 160 C. for 15 min. The contents of the reaction were then filtered and the DMF removed under high vacuum. The residue was triturated with MeOH to afford the title compound (0.560 g, 66%). MS (CI) m/e 337.9 (M+H); 1H NMR (300 MHz, CDCl3) delta ppm 3.92 (s, 3H) 7.05-7.31 (m, 5 H) 7.60 (d, J=2.21 Hz, 1H) 7.78 (dd, J=20.59, 8.82 Hz, 1H).

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 43

59
[ 4175-78-4 ]
[ 122-37-2 ]
C₁₅H₁₁BrN₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate; In N,N-dimethyl-formamide; at 180℃; for 0.0833333h;Microwave irradiation;	EXAMPLE 49; 4-[2-(4-anilinophenoxy)-1,3-thiazol-5-yl]but-3-yn-2-ol; EXAMPLE 49A; A 5 mL microwave reaction tube was charged with 2,5-dibromothiazole (61 mg, 0.25 mmol), 4-phenylaminophenol (46 mg, 0.25 mmol), potassium carbonate (103 mg, 0.75 mmol) and dmf (1 mL). The tube was sealed and microwaved at 180 C. for 5 min. LC/MS of an aliquot in methanol showed a complete reaction. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were back-extracted with brine and dried over sodium sulfate, filtered and concentrated. The crude material was purified on a 5000 mg pre-packed silica gel column (7.5% EtOAc/Hexane) to provide 55 mg (63%) of Example 49A. Mass spec (ESD) 348.7 (M+H), 344.8 (M-H). 1H NMR (delta, DMSO):8.32 (s, 1H), 7.42 (s, 1H), 7.28-7.23 (m, 4H), 7.14-7.07 (m, 4H), 6.86 (t, 1H).

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 31

60
[ 4175-78-4 ]
[ 14938-35-3 ]
5-Bromo-2-(4-pentyl-phenoxy)-thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In dimethyl sulfoxide; at 130℃; for 0.5h;Microwave irradiation;	EXAMPLE 14; N-{1-methyl-3-[2-(4-pentylphenoxy-1,3-thiazol-5-yl]prop-2-ynyl}acetamide; EXAMPLE 14A; 5-Bromo-2-(4-pentyl-phenoxy)-thiazole; 4-Pentyl-phenol (221 mg, 1.35 mmol), 2,5-Dibromo-thiazole (300 mg, 1.2 mmol) and K2CO3 (187 mg, 1.35 mmol) were combined in DMSO (3.5 ml). The reaction was placed in the microwave for 30 minutes at 130° C. Upon completion the reaction was poured into water and diluted with EtOAc. The layers were separated and the organics were washed with 15percent NaOH and then with water again. The organics were combined, dried (Na2SO4), filtered and concentrated by rotary evaporation to provide crude Example 14A which was used without further purification. MS (ESI) m/z 326.4 (M+H+); 1H NMR (300 MHz, d3-methanol) delta ppm 0.84-0.96 (m, 2H) 1.25-1.41 (m, 3H) 1.48-1.71 (m, 2H) 2.42-2.53 (m, 1H) 2.60-2.68 (m, 2H) 3.25-3.34 (m, 1H) 7.18 (d, J=9.0 Hz, 2H) 7.23 (s, 1H) 7.27 (d, J=9.0 Hz, 2H).

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 24

61
[ 4175-78-4 ]
[ 39634-42-9 ]
5-bromo-2-{4-[4-(trifluoromethyl)phenoxy]phenoxy}-1,3-thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In N,N-dimethyl-formamide; at 13℃; for 2h;	EXAMPLE 88; N-[1-methyl-3-(2-{3-[4-(trifluoromethyl)phenoxy]phenoxy}-1,3-thiazol-5-yl)prop-2-ynyl]acetamid; EXAMPLE 88A; 5-bromo-2-{4-[4-(trifluoromethyl)phenoxy]phenoxy}-1,3-thiazole; A solution of <strong>[4175-78-4]2,5-dibromothiazole</strong> (243 mg, 1 mmol), and 4-(4-trifluoromethyl-phenoxy)-phenol (255 mg, 1 mmol) in DMF (10 mL) was treated with potassium carbonate (139 mg, 1 mmol) and the mixture was heated at 130 C. for 2 h. The reaction was cooled to 25 C., poured into water (40 mL) and extracted with diethyl ether (3×45 mL). The combined organic layers were washed with water (3×30 mL) and brine (30 mL), dried over sodium sulfate and concentrated on a rotary evaporator. The crude concentrate (3.2 g) was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 25% ethyl acetate in hexanes to provide 400 mg (96%) of Example 88A.

Reference： [1]Patent: US2006/178400,2006,A1 .Location in patent: Page/Page column 39

62
[ 4175-78-4 ]
[ 57260-71-6 ]
[ 623588-36-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 18h;	A solution of l-÷22 (5.0 g, 20.58 mmol) in DMF (50 mL) was treated with 1-Boc-piperizine (5.71 g,. 30.87 mol) and K2C03. After stirring at 70C for 18 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with ice water (50 mL) , followed by extraction with ethyl acetate (25 mL x 2). The combined organic layers were washed with brine (50 mL) , dried over anhydrous Na2S04 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (60-120 mesh) using 10% EtOAc in hexanes to give the desired product 1-23 (5.95 g, 83%) as a yellow syrup; LCriS : m/z 347.9 [M+l].· .
83%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 18h;	Step II: tert-butyl 4-(5-bromothiazol-2-yl)piperazine-1-carboxylate (1-23) A solution of 1-22 (5.0 g, 20.58 mmol) in DMF (50 mL) was treated with 1-Boc-piperizine (5.71 g, 30.87 mol) and K2CO3. After stirring at 70 C. for 18 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with ice water (50 mL), followed by extraction with ethyl acetate (25 mL*2). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (60-120 mesh) using 10% EtOAc in hexanes to give the desired product 1-23 (5.95 g, 83%) as a yellow syrup; LCMS: m/z 347.9 [M++1].
68%	With triethylamine; In tetrahydrofuran; at 160℃; for 0.5h;Microwave irradiation;	a) 4-(5-Bromo-thiazol-2-yl)-piperazine-l-carboxylic acid tert-butyl esterA mixture of 24.7 mmol <strong>[4175-78-4]2,5-dibromothiazole</strong>, 49.4 mmol tert-butyl 1- piperazinecarboxylate and 74.1 mmol triethylamine in 24 ml tetrahydrofuran in a sealed tube was heated at 160 0C for 30 min under microwave irradiation. The reaction mixture was concentrated and the residue was purified by chromatography (SiO2, ethyl acetate/heptane) to afford the title compound as a white crystalline solid (yield 68%). MS (m/e): 350.2 ({8IBr}M+H+, 100%), 348.2 ({79Br}M+H 98%).

50%

With triethylamine; In N,N-dimethyl-formamide; at 65℃; for 16h;

Take 100mL single-mouthed flask, were successively added <strong>[4175-78-4]2,5-dibromothiazole</strong> (2.0g, 8.3mmol), tert-butyl piperazine-1-carboxylate (1.54g, 8.3mmol), TEA (3.6mL, 24.9mmol) , DMF (20mL), 65 deg. C reaction 16h, concentrated to dryness to give a crude product, after purification of the crude product by column chromatography to give pure product 1.4g, yield: 50%.

Reference： [1]Patent: WO2015/88045,2015,A1 .Location in patent: Paragraph 0261
[2]Patent: US2017/8885,2017,A1 .Location in patent: Paragraph 0672; 0674
[3]Patent: WO2006/72436,2006,A1 .Location in patent: Page/Page column 36
[4]Patent: CN105712952,2016,A .Location in patent: Paragraph 0236; 0237; 0238

63
[ 4175-78-4 ]
[ 204513-31-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium borohydrid; In methanol; hexane; ethyl acetate; N,N-dimethyl-formamide;	Synthesis of 2-(Hydroxymethyl)-4-(tri-n-butylstannyl)-thiazole 363 as Illustrated in FIG. 53a . To a solution of <strong>[4175-78-4]2,5-dibromothiazole</strong> (358; 1.0 equiv) in anhydrous ether (0.1 M) was added n-BuLi (1.1 equiv) at -78 C., and the resulting solution was stirred at the same temperature for 30 min, before DMF (1.2 equiv) and hexamethylphosphoramide (HMPA, 1.1 equiv) were added at the same time. After being stirred at -78 C. for 30 min., the reaction mixture was slowly warmed up to room temperature over a period of 2 h. Hexane (2.0 mL) was added and the resulting mixture passed through a short silica cake with 30% ethyl acetate in hexanes. The solvents were evaporated to give the crude aldehyde 359 (72% yield), which was used in the next step without further purification. To the solution of the crude aldehyde 359 in methanol (0.1 M) was added sodium borohydride (2.0 equiv) at 25 C., and the resulting mixture was stirred at the same temperature for 30 min. EtOAc and hexanes were added, and the mixture passed through a short silica cake with ethyl acetate. The solvents were then evaporated and the crude product was purified by flash chromatography (20 To 50% ethyl acetate in hexanes) to give 2-hydroxymethyl-4-bromothiazole 360 in 88% yield.

Reference： [1]Patent: US6441186,2002,B1

64
[ 4175-78-4 ]
[ 106-45-6 ]
[ 915137-41-6 ]

Yield	Reaction Conditions	Operation in experiment
80.9%	With potassium carbonate; In acetonitrile; for 2h;Heating / reflux;	4-Methylbenzenethiol (10.2 g, 82 mmol) and 2,4-dibromothiazole (20 g, 82 mmol) were dissolved in acetonitrile (150 ml) and potassium carbonate (12.5 g, 90.5 mmol) was added. The mixture was heated under reflux for 2 hours, cooled to room temperature and filtered through Celite. The filtrate was concentrated and the residue purified by chromatography on silica gel (eluent 0-50% ethyl acetate in hexane). The product was isolated as orange oil which crystallised upon standing (19 g, 80.9 % yield). 1H-NMR (400 MHz, CDCl3): 2.40 (s, 3H, CH3), 7.25 (d, 2H, 2x CH), 7.53 (m, 3H, 3x CH).

Reference： [1]Patent: WO2006/123088,2006,A2 .Location in patent: Page/Page column 82

65
[ 4175-78-4 ]
[ 926296-77-7 ]
[ 926297-09-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 22h;	To a solution of ethyl (2E) -3- [2-hydroxy-4- (2- methoxyethoxy) phenyl]acrylate (1.48 g) in N, N- dimethylformamide (10 ml) were added 2, 5-dibromothiazole (1.61 g) and potassium carbonate (1.53 g) , and the mixture was stirred at 800C for 22 hr. After cooling, water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO,}) ,, and concentrated. The obtained residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:2, v/v) to give ethyl (2E) -3- [2- [ (5-bromo-l, 3-thiazol-2-yl) oxy]-4- (2- methoxyethoxy) phenyl] acrylate (1.69 g, yield: 71%) as a colorless oil.1H-NMR (300 MHz, CDCl3) delta-'l-31 (3 H, t, J = 7.2 Hz), 3.43 (3 H, s), 3.73 - 3.75 (2 H, m) , 4.10 - 4.14 (2 H, m) , 4.23 (2 H,- q, J = 7.2 Hz), 6.37 (1 H, d, J = 16.1 Hz), 6.83 (1 H, s) , 6.87 (1 H, d, J = 8.7 Hz), 7.16 (1 H, s) , 7.60 (1 H, d, J = 8.7 Hz) , 7.79 (1 H, d, J = 16.1 Hz) .

Reference： [1]Patent: WO2007/18314,2007,A2 .Location in patent: Page/Page column 187

66
[ 4175-78-4 ]
[ 100243-39-8 ]
(S)-3-hydroxy-1-(2-thiazolyl)pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 80℃; for 17h;	A mixture of <strong>[4175-78-4]2,5-dibromothiazole</strong> (15.0 g, 59.9 mmol), (S)-3-hydroxypyrrolidine (6.00 mL, 71.9 mmol) and DIPEA (13.3 mL, 77.9 mmol) in dioxane (875 mL) was stirred at 80 C. for 17 h. The solvents were removed under reduced pressure. Aq. sat. NaHCO3 was added, and the mixture was extracted with CH2Cl2 (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. The crude title product (12.2 g) was used in the next reaction without purification. LC-MS: tR=0.54 min; ES+: 249.06.

Reference： [1]Patent: US2009/88457,2009,A1 .Location in patent: Page/Page column 13

67
[ 4175-78-4 ]
tropine [ No CAS ]
5-bromo-2-[(endo)-8-methyl-8-azabicyclo[3.2.1]octan-3-yloxy]thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 1; 2-[(ggrfO)-8-Methyl-8-azabicyclo[3.2 l]octan-3-yloxy]-5-(lH-indol-5-yl)-thiazole bis(hydrochloric acid)Example IA5-Bromo-2-[(g»^)-8-methyl-8-azabicyclo[3.2.1]octan-3-yloxy]thiazole Tropme (Aldnch, 420 mg, 3.0 mmol) in THF (anhydrous, Aldrich, 20 mL) "was treated with potassium /<?/f-butoxide (Aldnch, 350 mg, 3.50 mmol) at ambient temperature for 1.0 hour. A solution of <strong>[4175-78-4]2,5-dibromothiazole</strong> (Aldnch, 969 mg, 4.0 mmol) in THF (anhydrous, Aldnch, 10 <n="33"/>mL) was added to the above solution at 10-20 0C. The mixture was then stirred at ambient temperature for 3 hours. The mixture was quenched with water (1 mL) and concentrated under reduced pressure. The residue was diluted with CHCl3 (100 mL) and washed with brine (2 x 10 mL). The organic solution was concentrated under reduced pressure and the residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH3 -H2O, v 90/10/2, 1^=0.15) to give the title compound. 1H NMR (300 MHz, CD3OD) delta ppm 2.00-2.12 (m, 8 H), 2.36 (s, 3 H), 3.17 - 3.29 (m, 2 H), 5.10 (tJ=5.09 Hz, 1 H), 7.12 (s, 1 H); MS (DCI/NH3) m/z 303 (M+l)+. 305 (M+ 1)+.

Reference： [1]Patent: WO2009/67579,2009,A1 .Location in patent: Page/Page column 31-32

68
[ 4175-78-4 ]
[ 109-81-9 ]
N₁-(5-bromothiazol-2-yl)-N₁-methylethane-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With copper; copper(l) chloride; In isopropyl alcohol; at 70℃; for 1h;	Synthesis of Exemplary Compound 31: N-(2-((5-Bromothiazol-2-yl)(methyl)amino)ethyl)-3-(3-chlorophenyl)propiolamide; a) Synthesis of N1-(5-bromothiazol-2-yl)-N1-methylethane-1,2-diamine; 15 mg (0.24 mmol) of copper and 68 mg (0.69 mmol) of copper(I) chloride were added to a solution of 1.0 g (4.1 mmol) of <strong>[4175-78-4]2,5-dibromothiazole</strong> and 2.2 ml (24.7 mmol) of N-methylethylenediamine in isopropanol (2.3 ml). The mixture was then heated to 70 C. for 1 h. After cooling to RT, filtration through silica gel was carried out and the filtrate was evaporated under a vacuum. 348 mg (1.5 mmol, 36%) of N1-(5-bromothiazol-2-yl)-N1-methylethane-1,2-diamine were obtained by CC (DCE/EtOH/conc. aq. NH4-OH soln. 5:1:0.06) with the residue.

Reference： [1]Patent: US2009/176756,2009,A1 .Location in patent: Page/Page column 54

69
[ 110-91-8 ]
[ 4175-78-4 ]
[ 933728-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethanol; at 150℃; for 2h;	Step 1: A solution of <strong>[4175-78-4]2,5-dibromothiazole</strong> (1.0 equiv.), morpholine (1.5 equiv.) and triethylamine (4 equiv.) were heated to 150 C. for 2 h in the microwave. After concentration, the mixture was partitioned between water and EtOAc. The organic phase was washed with brine and dried over sodium sulfate. The solution was concentrated and dried under vacuo to give crude N-(4-methyl-3-(2-morpholinothiazol-5-yl)phenyl)-3-(trifluoromethyl)benzamide and was used in the next step without further purification. LCMS (m/z) (M+H)=448.2, Rt=0.83 min.

Reference： [1]Patent: US2014/275003,2014,A1 .Location in patent: Paragraph 0708; 0709

70
[ 109-01-3 ]
[ 4175-78-4 ]
[ 623588-32-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine; In tetrahydrofuran; at 20 - 90℃;Inert atmosphere;	Step 1In an argon atmosphere, 1-methylpiperazine (4.1 mL, 37.0 mmol) and triethylamine (5.1 mL, 37.0 mmol) were added at room temperature to a tetrahydrofuran (10 mL) solution of <strong>[4175-78-4]2,5-dibromothiazole</strong> (1.5 g, 6.17 mmol) It was. After heating under reflux overnight at 90 C., the solvent was distilled off under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography method (chloroform / methanol) to obtain the title compound (1.55 g, 96%).

Reference： [1]Patent: JP6378918,2018,B2 .Location in patent: Paragraph 0677; 0678

71
[ 4175-78-4 ]
[ 656825-80-8 ]
[ 915135-81-8 ]

Yield	Reaction Conditions	Operation in experiment
98%		Thiourea (86 mg, 1.05 mmol) was added to a solution of <strong>[4175-78-4]2,5-dibromothiazole</strong> (243 mg, 1 mmol) in ethanol (10 ml) at room temperature. The solution was heated under reflux for 2.5 hours. The reaction mixture was cooled to room temperature. To the reaction mixture was added 4-bromomethyl-l-methyl-5-(2,2,2-trifluoroethoxy)-3- trifluoromethyl-l//-pyrazole (341 mg, 1 mmol) (see Example 13 or Example 14), followed by potassium carbonate (179 mg, 1.3 mmol). The mixture was heated under reflux for 30 minutes, then cooled and stored at room temperature for 16 hours. The reaction mixture was filtered and the solid washed with ethyl acetate. The combined organic phases were concentrated and the residue purified by chromatography on silica gel (eluent 0-50% ethyl acetate in hexane) to yield Compound No. 1.001 of Table 32 as a colourless oil (448 mg, 98% yield).

Reference： [1]Patent: WO2006/123088,2006,A2 .Location in patent: Page/Page column 75

72
[ 4175-78-4 ]
[ 10365-98-7 ]
[ 1078734-00-5 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 6725 - 6739

73
[ 4175-78-4 ]
[ 5720-07-0 ]
[ 778581-58-1 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 6725 - 6739

74
[ 4175-78-4 ]
[ 1026688-00-5 ]
(4s)-4-(5-bromothiazol-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane N-borane complex [ No CAS ]
(4r)-4-(5-bromothiazol-2yloxy)-1-azatricyclo[3.3.1.13,7]decane N-borane complex [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 1-azaadamantan-4-ol (or 1-azaadamantan-4-ol N-borane complex, 1 eq.) and a heteroaryl halide (1 1 eq.) in anhydrous tetrahydrofuran (~0.5 M) was chilled to 0 C under a nitrogen atmosphere and treated with potassium tert- butoxide in THF (1.0 M; 1 eq ; Aldrich), added dropwise. The ice bath was removed, <n="63"/>and the mixture was allowed to warm to room temperature overnight. After diluting with water, the mixture was extracted with chloroform (3x), and the combined extracts were purified by flash chromatography (silica gel eluting with a gradient of 5- 10% MeOH-CHCl3 containing 1% NH4OH) to afford the desired product; (4r)-4-(5-Bromo-thiazol-2yloxy)1-aza-tricyclo[3.3.1.13,7]decane (130A1) and (4s)-4-(5-Bromo-thiazol-2yloxy)1-aza-tricyclo[3.3.1.13,7]decane (130A2) A solution of the product of Example 9A (2.4:1 diastereomer mixture; 334 mg, 2.0 mmol) and <strong>[4175-78-4]2,5-dibromothiazole</strong> following the etherification method B to provide a mixture of N-borane complex diastereomers. The diastereomers were separated by silica gel chromatography eluting with hexane/ethyl acetate to furnish the 4r -isomer as the minor product and the 4s-isomer as the major product. Then each isomer was subjected to acidic deboronation Method C to give the titled compounds 130Al and <n="157"/>130A2. Minor product 130A1 : 1H NMR (300 MHz, methanol-D4) delta ppm 1.70 - 1 75 (m, 1 H), 1.95 - 2.13 (m, 4 H), 2.17 (d, J=2, 7 Hz, 1 H), 2 21 (d, J=2.4 Hz, 1 H), 2.97 (d,J=1.4 Hz, 1 H), 3.01 (d, J=1 4 Hz, 1 H), 3.13 (s, 2 H), 3.37 (s, 1 H), 3.41 (s, 1 H), 5 23 (t, J=3.4 Hz, 1 H), 7.11 (s, 1 H). MS (DCI/NH3) m/e= 315, 317 (M+H)+. Major product 130 A2: Major product 130A2: 1H NMR (300 MHz, methanol-D4) delta ppm 1.67 (s, 1 H), 1.85 (s, 1 H), 1.89 (s, 1 H), 2.13 - 2.30 (m, 4 H), 3.05 - 3.16 (m, 4 H), 3.26 (s, 1 H), 5.22 (t, J=3.4 Hz, 1 H), 7.11 (s, 1 H) . MS (DCI/NH3) m/e= 315, 317 (M+H)+.

Reference： [1]Patent: WO2008/58096,2008,A2 .Location in patent: Page/Page column 61-62; 155-156

75
[ 4175-78-4 ]
(4s)-4-(1-azatricyclo[3.3.1.13,7]decan-4-ol) N-borane complex [ No CAS ]
(4s)-4-(5-bromothiazol-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane N-borane complex [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; at -20 - 20℃; for 1.25 - 2.25h;Product distribution / selectivity;	A solution of 1-azaadamantan-4-ol N-borane complex (1 eq.) and a heteroaryl halide (1.1 eq.) in anhydrous DMF (0.5-1 M) was chilled to between -20 and 0 C and treated with sodium hydride (1.5 equiv; 95%, Aldrich). After 15 minutes, the cooling bath was removed and the mixture was allowed to warm to room temperature. When 1 -azaadamantan-4-ol N-borane complex was consumed as determined by TLC analysis (generally 1-2 hours), the mixture was diluted with water and stirred for 1 hour. The resulting solid product was collected by filtration, washed with water, and dried under reduced pressure to afford the desired product; (4s)-4-(5-Bromothiazol-2-yloxy)-1-azatricyclo[3.3.1.13,7]decane N-borane complex Prepared from the product of Example 10A (1.67 g, 10.0 mmol) and 2,5- dibromothiazole (2.90 g, 11.9 mmol; Aldrich) according to Method A: 1H NMR (300 MHz, chloroform-D) delta ppm 1.69 (d, J=12.2 Hz, 2 H), 2.01 (s, 1 H), 2.19 (d, J=12.9 Hz, 2 H), 2.39 (s, 2 H), 3.13 - 3.25 (m, 6 H), 5.19 (t, J=3 4 Hz, 1 H), 7.03 (s, 1 H). MS (DCI/NH3) m/z= 329/331 (M+H)+.

Reference： [1]Patent: WO2008/58096,2008,A2 .Location in patent: Page/Page column 61; 80

76
[ 4175-78-4 ]
[ 6165-69-1 ]
[ 56421-76-2 ]
[ 128140-99-8 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1733 - 1739

77
[ 4175-78-4 ]
[ 5720-07-0 ]
[ 72997-45-6 ]
[ 778581-58-1 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1733 - 1739

78
[ 4175-78-4 ]
[ 13922-41-3 ]
[ 1210372-89-6 ]
2,5-di(1-naphthyl)-1,3-thiazole [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1733 - 1739

79
[ 4175-78-4 ]
[ 135884-31-0 ]
[ 1210372-90-9 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1733 - 1739

80
[ 4175-78-4 ]
[ 98-80-6 ]
[ 53715-67-6 ]
[ 3704-40-3 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1733 - 1739

81
[ 4175-78-4 ]
[ 1216058-85-3 ]
[ 1241953-98-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In dimethyl sulfoxide; at 110℃; for 2h;Inert atmosphere;	A mixture of 3,4-dihydrospiro[chromene-2,4'-piperidin]-5-ol (504 mg, 2.30 mmol), 2,5- dibromothiazole (583 mg, 2.400 mmol), and K2CO3 (795 mg, 5.75 mmol) was suspended in dry DMSO (5 ml), and stirred under N2 at an external temperature of 110 0C for 2 h. The reaction mixture was then cooled down to room temperature, and poured on 5% KHSO4 in water. After stirring for 10 min, the precipitate was collected to give the title compound as a brown solid residue, which was stored under vacuum for 5 h prior to use.

Reference： [1]Patent: WO2010/94120,2010,A1 .Location in patent: Page/Page column 109

82
[ 4175-78-4 ]
[ 1241953-54-7 ]
[ 1241954-06-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 120℃; for 16h;	A mixture of <strong>[4175-78-4]2,5-dibromothiazole</strong> (0.975 g, 4.01 mmol), 5-chloro-3,4-dihydrospiro[chromene-2,4'- piperidine] HCl salt (1 g, 3.65 mmol) and DBU (1.3 mL, 8.62 mmol) in DMF (15 mL) was heated at 120 0C for 16 h. After cooling, the mixture was diluted with water and extracted with CH2Cl2. The CH2Cl2 extract was washed with water (3x), dried (Na2SO4) and concentrated. The resulting residue was dissolved in CH2Cl2 and passed through a short silica pad (eluting with CH2Cl2ZEtOAc (1:1). After evaporation of the filtrate, the resulting residue was swished with Et2O, filtered and dried to give the title compound as a beige powder.

Reference： [1]Patent: WO2010/94120,2010,A1 .Location in patent: Page/Page column 115

83
[ 4175-78-4 ]
[ 178419-47-1 ]
[ 892548-09-3 ]

Yield	Reaction Conditions	Operation in experiment
		Sodium hydride (60% suspension in mineral oil) (15 mg, 0.36 mmol) was added to a solution of (3delta)-spiro[l-azabicyclo[2.2.2]octan-3,5'-oxazolidin-2'-one] (55 mg, 0.30 mmol) in anhydrous N,N-dimethylformamide (0.8 mL), and the resulting mixture was stirred for 30 min at 50 C. 2,5-Dibromothiazole (87 mg, 0.36 mmole) was added into the reaction mixture, which was then stirred at 50 C overnight. The solution was allowed to cool to room temperature, and then saturated aqueous ammonium chloride was added. The resulting mixture was extracted with chloroform, and the chloroform layer was washed with saturated aqueous potassium carbonate, then dried (MgSO4), filtered, and evaporated. The residue was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give the title compound as a yellow oil (11 mg); m/z 344, 346(MH+).

Reference： [1]Patent: WO2006/65209,2006,A1 .Location in patent: Page/Page column 17

84
[ 4175-78-4 ]
[ 2999-46-4 ]
[ 901122-44-9 ]

Yield	Reaction Conditions	Operation in experiment
91.9%		Example 3; A suspension of sodium hydride (60% in mineral oil, 13.6 g, 368 mmol) in N,N-dimethylformamide (160 ml) was cooled to -10C or below under a nitrogen atmosphere. Ethyl isocyanoacetate (36.2 g, 320 mmol) was gradually added dropwise to the cooled suspension, and the mixture was stirred at -3 to 5C for 2 h. This solution was cooled to -20C or below and was added dropwise to a solution of <strong>[4175-78-4]2,5-dibromothiazole</strong> (38.8 g, 160 mmol) in N,N-dimethylformamide over a period of about 20 min, and the mixture was stirred at -5 to -20C for 2 h. Water (8 ml) was added thereto to stop the reaction, and the reaction solution was added to 15 wt% brine (960 ml) under ice cooling. Subsequently, the mixture was adjusted to pH 6 to 7 by the addition of 1 M hydrochloric acid. Subsequently, common salt (102 g) was added thereto at the same temperature, and the mixture was stirred overnight. The resultant precipitate was collected by filtration, was washed with water (136 ml), and was dried under reduced pressure to give ethyl 2-bromoimidazo[5,1-b]thiazole-7-carboxylate (40.4 g, yield 91.9%).
90%		Synthesis of ethyl 2-bromoimidazo[5,1-b]thiazole-7-carboxylate; [Show Image] Example 2; Ethyl isocyanoacetate (0.9 ml, 8.2 mmol) was gradually added dropwise to a suspension of sodium hydride (60% in mineral oil, 378 mg, 9.4 mmol) in N,N-dimethylformamide (5 ml) in an argon atmosphere under ice cooling. The mixture was stirred at the same temperature for 2 h. This solution was added dropwise to a solution of <strong>[4175-78-4]2,5-dibromothiazole</strong> (1.0 g, 4.1 mmol) in tetrahydrofuran (13 ml) cooled to -20C (brine/ice water) through a cannula over a period of 20 min, and, while allowing the temperature to rise to around 0C, the mixture was stirred for 2 h. After the completion of the reaction, saturated brine was added thereto, and the mixture was extracted with ethyl acetate (20 ml x 5). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was washed with ethyl acetate to give ethyl 2-bromoimidazo[5,1-b]thiazole-7-carboxylate. The solvent was removed from the ethyl acetate washing liquor by distillation, and the residue was purified by chromatography on silica gel (hexane : ethyl acetate = 1 : 2). The resultant purification product was combined with the crystal prepared above to give ethyl 2-bromoimidazo[5,1-b]thiazole-7-carboxylate (1.1 g, 90%) as a white solid. 1H-NMR (500 MHz, CDCl3):delta 1.42 (3H, t, J = 7.2 Hz), 4.41 (2H, q, J = 7.2 Hz), 7.60 (1H, s), 7.96 (1H, s). 13C-NMR (125 MHz, CDCl3): delta 14.5, 60.9, 108.2, 118.5, 122.1, 127.3, 137.7, 162.0. FT-IR (neat, cm-1): 3107, 3008, 1705, 1508, 1475, 1454, 1377, 1338, 1325, 1250, 1159, 1109, 1045, 1022, 953, 837, 771, 644. m.p. 171 - 172C (recrystallized from ethyl acetate)

Reference： [1]Patent: EP1840129,2007,A1 .Location in patent: Page/Page column 12
[2]Patent: EP1840129,2007,A1 .Location in patent: Page/Page column 12

85
[ 4175-78-4 ]
[ 39687-95-1 ]
[ 901122-43-8 ]

Yield	Reaction Conditions	Operation in experiment
85%		Synthesis of methyl 2-bromoimidazo[5,1-b]thiazole-7-carboxylate; [Show Image] Example 1; Methyl isocyanoacetate (0.63 ml, 6.9 mmol) was gradually added dropwise to a suspension of sodium hydride (60% in mineral oil, 346 mg, 8.6 mmol) in N,N-dimethylformamide (5 ml) in an argon atmosphere under ice cooling, and the mixture was stirred at the same temperature for 2 h. This solution was added dropwise to a solution of <strong>[4175-78-4]2,5-dibromothiazole</strong> (1.0 g, 4.1 mmol) in tetrahydrofuran (10 ml) cooled to -20C (brine/ice water) through a cannula over a period of 15 min, and, while allowing the temperature to rise to about 0C, the mixture was stirred for 2 h. After the completion of the reaction, saturated brine was added thereto, and the mixture was extracted with dichloromethane (20 ml x 5). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was washed with ethyl acetate to give methyl 2-bromoimidazo[5,1-b]thiazole-7-carboxylate (910 mg, 85%) as a white solid. 1H-NMR (500 MHz, CDCl3): delta 3.95 (3H, s), 7.62 (1H, s), 7.97 (1H, s). 13C-NMR (125 MHz, CDCl3): delta 51.9, 108.2, 118.6, 121.8, 127.4, 137.8, 162.4. FT-IR (KBr, cm-1): 3133, 3033, 3013, 1715, 1507, 1433, 1383, 1343, 1250, 1148, 1046. EI-MS (m/z): 262, 260, 231, 204, 202, 191, 189. Sublimated at 150C or above.

Reference： [1]Patent: EP1840129,2007,A1 .Location in patent: Page/Page column 11-12

86
[ 4175-78-4 ]
[ 1258933-04-8 ]
[ 1258934-18-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene;Inert atmosphere; Reflux;	Example 105; 4-[5-(4-methoxyphenyl)-1,3-thiazol-2-yl]-1,4-diazatricyclo[4.3.1.13,8]undecane; Example 105A 4-(5-bromo-1,3-thiazol-2-yl)-1,4-diazatricyclo[4.3.1.13,8]undecane To a solution of the product of Example 2 (1 g, 6.55 mmol) in toluene (50 mL) under nitrogen was added <strong>[4175-78-4]2,5-dibromothiazole</strong> (3.18 g, 13.1 mmol), potassium carbonate (1.80 g, 13.1 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (403 mg, 0.655 mmol) and palladium(II) acetate (74 mg, 0.328 mmol). The mixture was stirred overnight at reflux. After cooling, the reaction mixture was concentrated under reduced pressure and the residue was purified by chromatography on silica gel (1:2 petroleum ether-ethyl acetate) to afford the title compound: 1H NMR (500 MHz, CDCl3) delta ppm 7.40 (s, 1H), 4.75-4.71 (m, 1H), 3.64-3.59 (q, 2H), 3.48-3.40 (q, 2H), 3.08-3.05 (m, 4H), 2.29-2.18 (m, 3H), 1.88-1.80 (m, 3H).

Reference： [1]Patent: US2010/324027,2010,A1 .Location in patent: Page/Page column 32

87
[ 4175-78-4 ]
[ 942070-45-3 ]
2-bromo-5-(1H-indol-3-yl)thiazole [ No CAS ]
2,4-di(1H-indole-3-yl)thiazole [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 4564 - 4569

88
[ 4175-78-4 ]
[ 851524-96-4 ]
5-(5-bromothiazol-2-yl)pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; toluene; at 80℃; for 16h;Inert atmosphere;	To a solution of <strong>[851524-96-4](6-amino-3-pyridyl)boronic acid</strong> (200.00 mg, 1.45 mmol, 1.00 eq.) in dioxane (5.00 mL), Tol. (5.00 mL) and H20 (2.00 mL) were added Pd(dppf)Cl2.CH2Cl2 (118.41 mg, 145.00 muetaomicron, 0.10 eq.), Na2C03 (461.06 mg, 4.35 mmol, 3.00 eq.) and 2,5- dibromothiazole (528.35 mg, 2.18 mmol, 1.50 eq.). The mixture was stirred at 80C for 16 hrs under N2 and LCMS showed the reaction was complete. The mixture was concentrated and the residue was purified by prep-TLC (PE:EtOAc = 1:2) to give 5-(5-bromothiazol-2- yl)pyridin-2-amine (100.00 mg, crude) as a yellow solid. ESI [M+H] = 257.7/255.7

Reference： [1]Patent: WO2019/14315,2019,A1 .Location in patent: Page/Page column 90

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P378
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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Health hazards
Code	Phrase
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H317	May cause an allergic skin reaction
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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. 4175-78-4 ] {[proInfo.proName]}

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[ 4175-78-4 ] Synthesis Path-Upstream 1~6

[ 4175-78-4 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 4175-78-4 ]

Bromides

Related Parent Nucleus of [ 4175-78-4 ]

Thiazoles

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[ 4175-78-4 ]

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[ 4175-78-4 ]