[ CAS No. 41731-23-1 ]

Name: 41731-23-1|2-Bromo-5-methylthiazole|97%
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Product Details of [ 41731-23-1 ]

CAS No. :	41731-23-1	MDL No. :	MFCD08460610
Formula :	C₄H₄BrNS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FJPZHYAYNAUKKA-UHFFFAOYSA-N
M.W :	178.05	Pubchem ID :	21906106
Synonyms :

Calculated chemistry of [ 41731-23-1 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.78
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) :	-5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.99
Log Po/w (XLOGP3) :	2.38
Log Po/w (WLOGP) :	2.21
Log Po/w (MLOGP) :	0.92
Log Po/w (SILICOS-IT) :	3.3
Consensus Log Po/w :	2.16

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.97
Solubility :	0.19 mg/ml ; 0.00107 mol/l
Class :	Soluble
Log S (Ali) :	-2.88
Solubility :	0.232 mg/ml ; 0.0013 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.53
Solubility :	0.524 mg/ml ; 0.00294 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.52

Safety of [ 41731-23-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 41731-23-1 ]

* 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 [ 41731-23-1 ]
Downstream synthetic route of [ 41731-23-1 ]

[ 41731-23-1 ] Synthesis Path-Upstream 1~7

1
[ 41731-23-1 ]
[ 68-12-2 ]
[ 13838-78-3 ]

Reference： [1] Patent: US2014/275528, 2014, A1, . Location in patent: Paragraph 0281; 0282
[2] Patent: WO2014/143799, 2014, A2, . Location in patent: Page/Page column 368

2
[ 7305-71-7 ]
[ 41731-23-1 ]

Reference： [1] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14622 - 14626
[2] Chemical Communications, 2011, vol. 47, # 1, p. 460 - 462
[3] Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 23, p. 11356 - 11360
[4] Patent: EP1721905, 2006, A1, . Location in patent: Page/Page column 37
[5] Journal of the American Chemical Society, 2013, vol. 135, # 9, p. 3407 - 3410

3
[ 7305-71-7 ]
[ 7789-45-9 ]
[ 41731-23-1 ]

Reference： [1] Patent: US2004/97425, 2004, A1,

4
[ 3581-89-3 ]
[ 41731-23-1 ]

Reference： [1] Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 758,763

5
[ 110-85-0 ]
[ 41731-23-1 ]
[ 118113-05-6 ]

Reference： [1] Patent: US2007/112011, 2007, A1,

6
[ 41731-23-1 ]
[ 131748-91-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With N-Bromosuccinimide In dichloromethane; water at 90℃; for 3 h; UV-irradiation; Reflux	Step 1: Synthesis of 2-bromo-5-(bromomethyl)thiazole. A solution of 2- bromo-5-methylthiazole (1 g, 5.6 mmol) and N-bromosuccinimide (1.1 g, 6.18mmol, 1.1 eq) in 40 mL of DCM and 40 mL of H20 was stirred under UVirradiation at 90°C in a round bottom flask outfitted with a reflux condenser for 3 hours. The reaction was then cooled to room temperature, poured into aseparatory funnel, and extracted. The aqueous layer was extracted twice more with DCM, the organic layers combined, dried with MgSO4, filtered through cotton, concentrated and purified by automated chromatography with a 0percent to 3percent gradient of EtOAc in hexanes to yield 1.24 g (78percent). ‘H NMR (400 MHz, CDC13) d 7.46 (d, J 0.9 Hz, 1H), 4.57 (d, J 0.9 Hz, 3H). ‘C NMR (101 MHz,CDC13) d 141.92, 139.80, 137.39, 22.37. MS (ESI): m/z: 255.8 [M+H].

Reference： [1] Patent: WO2014/145331, 2014, A1, . Location in patent: Page/Page column 68; 69
[2] Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 1, p. 204 - 212
[3] Patent: US2015/51402, 2015, A1, . Location in patent: Paragraph 0084
[4] Patent: US5034404, 1991, A,

7
[ 41731-23-1 ]
[ 1206708-88-4 ]

Yield	Reaction Conditions	Operation in experiment
36%	With bromine In chloroform; acetonitrile for 16 h; Reflux	Step 1 : To a solution of 2-bromo-5-methyl-thiazole (3.0 g, 16.9 mmol) in a mixture of CHCI₃ (30 mL) and CH₃CN (30 mL) was added bromine (2.6 mL, 50.6 mmol) and the RM was heated at reflux for 16 h. The RM was quenched with sodium thiosulfate solution and extracted with CH₂CI₂. The combined organic layers were washed with water and brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by CC (Si0₂, EtOAc/Hex) to yield 2,4-dibromo-5-methyl-thiazole (1.6 g, 36percent).

Reference： [1] Journal of Materials Chemistry C, 2015, vol. 3, # 16, p. 4156 - 4161
[2] Journal of the American Chemical Society, 2015, vol. 137, # 7, p. 2738 - 2747
[3] Patent: WO2015/22073, 2015, A1, . Location in patent: Page/Page column 108

[ 41731-23-1 ] Synthesis Path-Downstream 1~64

1
[ 3581-89-3 ]
[ 41731-23-1 ]

Reference： [1]Proceedings - Indian Academy of Sciences, Section A,1953,p. 758,763

2
[ 109-83-1 ]
[ 41731-23-1 ]
2-[methyl-(5-methyl-thiazol-2-yl)-amino]-ethanol [ No CAS ]

Reference： [1]Yakugaku Kenkyu,1958,vol. 30,p. 248,255
Chem.Abstr.,1960,p. 512

3
[ 41731-23-1 ]
[ 6325-93-5 ]
[ 855230-93-2 ]

Reference： [1]Patent: US2362087,1939,
[2]Patent: US2385224,1939,

4
[ 41731-23-1 ]
[ 63-74-1 ]
[ 953-90-2 ]

Reference： [1]Proceedings - Indian Academy of Sciences, Section A,1953,p. 758,763

5
diazotized 5-methyl-thiazol-2-ylamine [ No CAS ]
[ 41731-23-1 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 6260

6
[ 41731-23-1 ]
[ 847547-16-4 ]

Yield	Reaction Conditions	Operation in experiment
		(2) A 2.59M solution of n-butylithium in hexane (2.40 ml) was added dropwise to a solution of 2-bromo-5-methyltiazole (1.00 g) in tetrahydrofuran (10 ml) at -78C, and the mixture was stirred for 40 minutes at the same temperature. A solution of iodine (1.55 g) in tetrahydrofuran (5 ml) was added dropwise thereto at -78C, and the mixture was stirred for 30 minutes at the same temperature. A saturated aqueous solution of ammonium chloride (20 ml) was added to the reaction solution so as to quench the reaction, and this solution was left to room temperature. This solution was charged with water (20 ml) and extracted twice with ethyl acetate (100 ml). The organic layer was washed with a saturated aqueous solution of sodium thiosulfate (50 ml), and then dried over anhydrous magnesium sulfate. After the solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=85:15) to yield 2-iodo-5-methylthiazole (764 mg) as a brown oil. 1H NMR (300 MHz, CDCl3) delta ppm: (300 MHz, CDCl3) deltappm: 2.47 (3H, d, J = 1.2 Hz), 7.26 (1H, d, J = 1.2 Hz)

Reference： [1]Patent: EP1721905,2006,A1 .Location in patent: Page/Page column 38

7
[ 7305-71-7 ]
[ 41731-23-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 0℃; for 3h;	(1) After t-butyl nitrite (1.99 g) was added dropwise to a suspension of 2-amino-5-methyltiazole (2.00 g) in acetonitrile (20 ml) while ice-cooling, copper(II) bromide (4.30 g) was gradually added thereto. This suspension was stirred for 3 hours at 0C. The reaction solution was charged with 1N hydrochloric acid (100 ml) and then extracted twice with ethyl acetate (200 ml). After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated. The residue was purified by silica gel column chromatography (neutral; hexane:ethyl acetate=80:20) to yield 2-bromo-5-methylthiazole (1.31 g) as a yellow oil. 1H NMR (300 MHz, CDCl3) delta ppm: 2.44 (3H, d, J = 1.2 Hz), 7.25 (1H, d, J = 1.1 Hz)

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 14622 - 14626
[2]Chemical Communications,2011,vol. 47,p. 460 - 462
[3]Journal of Agricultural and Food Chemistry,2008,vol. 56,p. 11356 - 11360
[4]Patent: EP1721905,2006,A1 .Location in patent: Page/Page column 37
[5]Journal of the American Chemical Society,2013,vol. 135,p. 3407 - 3410

8
[ 41731-23-1 ]
[ 54166-95-9 ]
6-chloro-2-methyl-5H-[1,3]-thiazolo[2,3-b]quinazolin-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 12 2-methyl-6-chloro-5H-thiazolo-(2,3-b)-quinazolin-5-one (compound 14) 10.2 g of 6-chloroanthranilamide and 10.74 g of <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> were stirred at 140 C. for 2 hours. After working up in the conventional manner there was obtained 11.7 g (78%) of the above compound; m.p. 235-236 C.

Reference： [1]Patent: US5030727,1991,A

9
[ 110-85-0 ]
[ 41731-23-1 ]
[ 118113-05-6 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis of 1-(5-methylthiazol-2-yl)piperazine 1-(5-Methylthiazol-2-yl)piperazine was obtained by the reaction of <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> [Precursor BBB32] with piperazine according to the conditions described above Precursor BBB1.

Reference： [1]Patent: US2007/112011,2007,A1

10
[ 7305-71-7 ]
[ 7789-45-9 ]
[ 41731-23-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butylnitrite; In acetonitrile;	Preparation 30 2-Bromo-5-methyl-1,3-thiazole To a solution of 2-amino-5-methyl-1,3-thiazole (11.7 g) in acetonitrile (200 ml) was added dropwise tert-butyl nitrite (8.33 ml) at 0 C. followed by addition of copper(II) bromide (5 g) over 0.5 minutes. After stirring at 0 C. for 3 hours, the mixture was concentrated and partitioned between 1N hydrochloric acid and ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered through a pad of Celite, and concentrated in vacuo to give the title compound (3.24 g) as an oil. ESI-MS: 177.8(M+H) 1H-NMR (300 MHz, CDCl3) delta 7.25(s, 1H), 2.44(s, 3H).

Reference： [1]Patent: US2004/97425,2004,A1

11
[ 41731-23-1 ]
[ 131748-91-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With N-Bromosuccinimide; In dichloromethane; water; at 90℃; for 3h;UV-irradiation; Reflux;	Step 1: Synthesis of 2-bromo-5-(bromomethyl)thiazole. A solution of 2- bromo-5-methylthiazole (1 g, 5.6 mmol) and N-bromosuccinimide (1.1 g, 6.18mmol, 1.1 eq) in 40 mL of DCM and 40 mL of H20 was stirred under UVirradiation at 90C in a round bottom flask outfitted with a reflux condenser for 3 hours. The reaction was then cooled to room temperature, poured into aseparatory funnel, and extracted. The aqueous layer was extracted twice more with DCM, the organic layers combined, dried with MgSO4, filtered through cotton, concentrated and purified by automated chromatography with a 0% to 3% gradient of EtOAc in hexanes to yield 1.24 g (78%). ?H NMR (400 MHz, CDC13) d 7.46 (d, J 0.9 Hz, 1H), 4.57 (d, J 0.9 Hz, 3H). ?C NMR (101 MHz,CDC13) d 141.92, 139.80, 137.39, 22.37. MS (ESI): m/z: 255.8 [M+H].
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane;Reflux;	11.8 g of 2-bromo-5-methylthiazole, 18.85 g of N-bromosuccinicimide (NBS), 42.4 mg of azobisisobutyronitrile (AIBN), and carbon tetrachloride (150 mL), were added into a 250 mL single-neck flask equipped with a magnetic stirrer, and, the reaction mixture was stirred at reflux temperature for 20 to 30 hours. After cooling down, the reaction mixture was extracted by carbon tetrachloride. The organic layer was separated while the aqueous layer was extracted with carbon tetrachloride twice. The organic phases were combined, and dried over anhydrous sodium sulfate after washed with an iced aqueous sodium chloride solution twice, then remove the solvent under reduced pressure to obtain 13.8 g of 2-bromo-5-bromomethylthiazole which was used in the next reaction directly without purification
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;	REFERENCE EXAMPLE 8 A mixture of 4.45g of 2-bromo-5-methylthiazole, 4.89g of N-bromosuccinimide, 0.2g of benzoyl peroxide and 50ml of carbon tetrachloride was refluxed for 50 minutes and then cooled to room temperature. An insoluble substance was removed by filtration and the filtrate was concentrated. The residue was purified by a column chromatography [developing solvent: hexanedichloromethane (2:3)] to afford 4.53g of 2-bromo-5(bromomethyl) thiazole as a yellow solid. 1 H-NMR(CDCl3) 4.64(2H,s), 7.54(1H,s)

Reference： [1]Patent: WO2014/145331,2014,A1 .Location in patent: Page/Page column 68; 69
[2]Journal of Agricultural and Food Chemistry,2008,vol. 56,p. 204 - 212
[3]Patent: US2015/51402,2015,A1 .Location in patent: Paragraph 0084
[4]Patent: US5034404,1991,A

12
[ 41731-23-1 ]
[ 5188-07-8 ]
N-Hal-succinimide; Hal=Cl, Br [ No CAS ]
[ 1092391-06-4 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2008,vol. 56,p. 11356 - 11360

13
[ 41731-23-1 ]
[ 63968-64-9 ]
C₁₉H₂₇NO₅S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 3594 - 3601

14
[ 41731-23-1 ]
[ 1187451-03-1 ]
[ 1187451-04-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 90℃; for 24h;Inert atmosphere;	To tert-butyl [tert-butoxycarbonyl(6-{(pyridin-2-ylsulfonyl)[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzyl]aminomethyl}pyridin-2-yl)amino]acetate (404 mg) (containing 0.577 mmol of a pure content) obtained in Example 22-(b) were added <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (212 mg, 1.19 mmol), a mixed solvent (toluene:ethanol=7:3 (V/V), 11.5 ml) and a 2M aqueous sodium carbonate solution (0.58 ml), which was deaerated under reduced pressure, followed by argon substitution. Tetrakis(triphenylphosphine)palladium (66.6 mg, 0.0576 mmol) was then added, followed by stirring at 90C for 24 hours under argon atmosphere. After completion of the reaction, water was added to the reaction solution, followed by extraction with toluene. The separated organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=1:03:2 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (291 mg) as a yellow oil. (Yield: 76%) Mass spectrum (CI, m/z): 666 (M++1). 1H-NMR spectrum (CDCl3, ppm): 8.59 (ddd, J=4.7, 1.7, 1.0Hz, 1H), 7.81 (ddd, J=7.9, 1.6, 1.0Hz, 1H), 7.80-7.72 (m, 3H), 7.65 (d, J=7.8Hz, 1H), 7.51-7.42 (m, 2H), 7.38 (ddd, J=7.2, 4.7, 1.6Hz, 1H), 7.32-7.26 (m, 2H), 6.91 (dd, J=7.3, 0.7Hz, 1H), 4.74 (s, 2H), 4.49 (s, 2H), 4.45 (s, 2H), 2.51 (d, J=1.2Hz, 3H), 1.52 (s, 9H), 1.42 (s, 9H).
76%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 90℃; for 24h;Inert atmosphere;	22-(c) tert-Butyl [tert-butoxycarbonyl(6-[4-(5-methylthiazol-2-yl)benzyl](pyridin-2-ylsulfonyl)aminomethyl}pyridin-2-yl)amino]acetate To tert-butyl [tert-butoxycarbonyl(6-{(pyridin-2-ylsulfonyl)[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzyl]aminomethyl}pyridin-2-yl)amino] acetate (404 mg) (containing 0.577 mmol of a pure content) obtained in Example 22-(b) were added <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (212 mg, 1.19 mmol), a mixed solvent (toluene:ethanol=7:3 (V/V), 11.5 ml) and a 2M aqueous sodium carbonate solution (0.58 ml), which was deaerated under reduced pressure, followed by argon substitution. Tetrakis(triphenylphosphine)palladium (66.6 mg, 0.0576 mmol) was then added, followed by stirring at 90C for 24 hours under argon atmosphere. After completion of the reaction, water was added to the reaction solution, followed by extraction with toluene. The separated organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate= 1:0?3:2 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (291 mg) as a yellow oil. (Yield: 76%) Mass spectrum (CI, m/z): 666 (M++1). 1H-NMR spectrum (CDCl3, deltappm): 8.59 (ddd, J=4.7, 1.7, 1.0Hz, 1H), 7.81 (ddd, J=7.9, 1.6, 1.0Hz, 1H), 7.80-7.72 (m, 3H), 7.65 (d, J=7.8Hz, 1H), 7.51-7.42 (m, 2H), 7.38 (ddd, J=7.2, 4.7, 1.6Hz, 1H), 7.32-7.26 (m, 2H), 6.91 (dd, J=7.3, 0.7Hz, 1H), 4.74 (s, 2H), 4.49 (s, 2H), 4.45 (s, 2H), 2.51 (d, J=1.2Hz, 3H), 1.52 (s, 9H), 1.42 (s, 9H).

Reference： [1]Patent: EP2264009,2010,A1 .Location in patent: Page/Page column 94
[2]Patent: EP2415763,2012,A1 .Location in patent: Page/Page column 96

15
[ 41731-23-1 ]
[ 138547-96-3 ]
[ 1263497-11-5 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 460 - 462

16
[ 41731-23-1 ]
[ 121219-08-7 ]
[ 1263497-09-1 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 460 - 462

17
[ 41731-23-1 ]
[ 139962-95-1 ]
[ 1310531-81-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 20 - 120℃;Microwave irradiation;	To a solution of 2-formyl-4-methoxyphenylboronic acid (200 mg, 1.11 mmol) in DMF (10 mL) and H20 (2 mL) are added <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (217 mg, 1.22 mmol), Pd(PPh3)4 (128 mg, 0.11 mmol) and K2C03 (230 mg, 1.67 mmol) at room temperature. The solution is heated to 120 C for 1 hour in a microwave reactor. The solution is cooled down and 3-mercaptopropyl-functionalized silica gel (500 mg) is added. The solution is stirred for 15 minutes and filtered. The filtrate is washed with H20 (15 mL) and is extracted with EtOAc (3 x 15 mL). The combined organic layer is dried with MgS04 and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash chromatography eluting with 50% EtOAc in heptane to afford 5-methoxy-2-(5- methyl-thiazol-2-yl)-benzaldehyde (160 mg, 63%) as a white foam.

Reference： [1]Patent: WO2011/68821,2011,A1 .Location in patent: Page/Page column 81-82

18
[ 41731-23-1 ]
[ 98-80-6 ]
[ 5221-69-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 110℃; for 5h;Inert atmosphere;	Step 1 : A mixture of <strong>[41731-23-1]2-bromo-5-methyl-thiazole</strong> (2.0 g, 11.2 mmol), phenylboronic acid (1.64 g, 13.5 mmol) and K2C03 (22.5 mmol) in a mixture of dioxane (20 mL) and water (4 mL) was degassed through purging with Ar for 30 min. Pd(PPh3)4 (647 mg, 0.56 mmol) was added and the mixture was heated to 110C for 5 h. The volatiles were removed under reduced pressure, the residue was diluted with EtOAc, was washed with water and brine, dried and the volatiles were removed under reduced pressure. The residue was purified by CC (silica gel, EtOAc/Hex) to yield the desired compound (1.1 g, 56%). LC-MS (method 3): m/z [M+H]+ = 175.6 (MW calc. = 175.25); R, = 2.70 min.

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 5086 - 5098
[2]Patent: WO2015/22073,2015,A1 .Location in patent: Page/Page column 66
[3]Chemical Communications,2011,vol. 47,p. 7149 - 7151

19
[ 41731-23-1 ]
[ 1440-61-5 ]
[ 1375710-69-2 ]

Yield	Reaction Conditions	Operation in experiment
73%		Example 39a 2-Chloro-1-(5-methylthiazol-2-yl)ethanone Isopropylmagnesium bromide (CAS 920-39-8, 1 M in THF, 12.1 mL, 12.1 mmol) was added dropwise to a solution of <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (CAS 41731-23-1, 2.056 g, 11.55 mmol) in THF (20 mL) at 0 C. and the resulting solution was stirred for 15 min at 0 C. A solution of 2-chloro-1-morpholinoethanone (CAS 1440-61-5, 2.078 g, 12.70 mmol) in THF (5 mL) was added dropwise and the mixture was stirred at 0 C. for 45 min and then at room temperature for 1.5 h. The reaction was quenched by the addition of sat. aq. NH4Cl and the mixture was diluted with diethyl ether. The phases were separated and the aqueous phase was extracted with diethyl ether. The combined organic layers were washed with citric acid, water and sat. aq. NaHCO3, dried over MgSO4 and concentrated to give 2-chloro-1-(5-methylthiazol-2-yl)ethanone (1.48 g, 73%). MS m/z 176, 178 [M+H]+.
36%		[00349] 2-Chloro-l-(5-methylthiazol-2-yl)ethanone. Isopropylmagnesium chloride (2 M in Et20, 2.67 mL, 5.35 mmol) was added dropwise to a solution of <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (1.0 g, 5.62 mmol, 1.05 equiv.) in THF (10 mL) at 0C. The resulting solution was stirred for 15 min at 0C. A solution of 2-chloro-l-morpholinoethanone (959 mg, 5.88 mmol, 1.1 equiv.) in THF (3 mL) was added dropwise and the mixture was stirred at 0 C for 45 min and then at room temperature for 1.5 h. The reaction was quenched by the addition of sat. aq. NH4CI and the mixture was diluted with diethyl ether. The phases were separated and the aqueous phase was extracted with diethyl ether. The combined organic layers were washed with water and sat. aq. NaHCC>3, dried over MgS04 and concentrated to give 2-chloro-l-(5- methylthiazol-2-yl)ethanone. The crude product was purified using automated flash chromato raphy in 36 % isolated yield. ESI-MS (m/z): 176.1 [M+H]+.

Reference： [1]Patent: US2012/122843,2012,A1 .Location in patent: Page/Page column 42
[2]Patent: WO2016/168472,2016,A1 .Location in patent: Paragraph 00349

20
[ 41731-23-1 ]
[ 1414782-20-9 ]
[ 1414782-40-3 ]

Yield	Reaction Conditions	Operation in experiment
32%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 110℃; for 18h;Inert atmosphere;	General procedure: To an oven-dried round-bottom flask containing tert-butyl 2-[(R)-5-bromo-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate 3 (1.0 mmol) was added bis(pinacolato)diboron (1.1 mmol), potassium acetate (4.0 mmol) and 10 mL of anhydrous 1,4-dioxane. The resulting mixture was purged with N2 for three times. Pd(dppf)Cl2 (0.05 mmol) was added, the reaction mixture was purged with N2 again three times and heated under N2 at 110 C for 46 h. The course of the reaction was followed by TLC (5% MeOH in CH2Cl2) and LCMS. The reaction mixture was cooled to room temperature, and the aryl halide 5 (1.1 mmol)], Pd(dppf)Cl2 (0.05 mmol) and 3.5 mL of 2M aqueous solution of potassium carbonate (de-oxygenated by bubbling through N2 for 15 minutes before addition) were added. The reaction mixture was purged with N2 three times and then heated under N2 for 618 h at 110 C. The course of the reaction was followed by LCMS. The reaction mixture was cooled to room temperature, and the solvent removed under reduced pressure. The residue was partitioned between EtOAc (100 mL) and 1N NaOH solution (100 mL). The organic layer was washed with brine (100 mL), dried over Na2SO4 and the solvent was removed under reduced pressure to afford the crude product as a dark brown oil. The crude product was purified by silica gel chromatography, eluting with 010% MeOH in CH2Cl2 to afford the desired product.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6351 - 6354,4

21
[ 41731-23-1 ]
[ 4746-97-8 ]
[ 857650-92-1 ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 1039 - 1044

22
[ 41731-23-1 ]
[ 63503-60-6 ]
[ 1314389-89-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; at 50℃;	To a 20 mL microwave vial was added (3-chlorophenyl)boronic acid (512 mg, 3.28 mmol), 2-.bromo-5-methyl-1,3-thiazole (0.49 mL, 2.7 mmol), K2C03 (754 mg, 5.46 mmol), dioxane (9 mL), PdCl2(dppf DCM (100 mg, 0.136 mmol), and water (1 mL). The vial was sealed and stirred at 50C overnight. The crude product was dissolved in EtOAc, filtered through Celite and concentrated in vacuo. The residue was absorbed onto silica and purified by flash chromatography (MPLC, 30-100% EtOAc-Hexanes) to provide 2-(3-chlorophenyl)-5- methyl-1 ,3-thiazole.LRMS (ESI) calc'd for C10H9C1NS [M+H]+: 210, Found: 210

Reference： [1]Patent: WO2011/84402,2011,A1 .Location in patent: Page/Page column 125

23
[ 41731-23-1 ]
[ 244205-40-1 ]
[ 1423446-91-6 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 3407 - 3410

24
[ 41731-23-1 ]
[ 1066-45-1 ]
[ 1362243-44-4 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 10322 - 10325

25
[ 41731-23-1 ]
[ 123324-71-0 ]
C₁₄H₁₇NS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 3h;Inert atmosphere;	A 25-mL round bottom flask equipped with a magnetic stirrer, a condenser and a nitrogen in/outlet adapter was charged with <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (250 mg, 1.4 mmol), 4- tert-butyiphenylboronic acid (400 mg, 2.1 mmol), water/dioxane (1 mL/3 ml), K2C03 (386 mg, .2 mmol). The resulting solution was degassed for 5 minutes, then Pd(PPh3)4 (30 mg) was added. The reaction mixture was warmed to 100 C and stirred for 3 hours. After being allowed to cool to room temperature, the reaction mixture was diluted with EtOAc (100 mL) and washed with saturated NaHCO3, brine and then dried over Na2SO4. The organic layer was concentrated under reduced pressure and purified on silica gel. Elution with EtOAc/hexanes solvent system afforded the desired compound (145 mg, 45% yield). ?H NMR (300 MHz, CDC13) oe 7.81 (d, J 9.0 Hz, 2H), 7.47 (s, 1H), 7.43 (d, J= 9.0 Hz, 2H), 2.50 (s, 3H), 1.34 (s, 9H).

Reference： [1]Patent: WO2013/106761,2013,A2 .Location in patent: Page/Page column 49; 50

26
[ 41731-23-1 ]
[ 34941-91-8 ]
[ 1608483-00-6 ]

Yield	Reaction Conditions	Operation in experiment
24%		To a dry 10 mL Schlenk flask equipped with a stir bar and placed under N2 atmosphere was added <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (244 mg, 1.37 mmol) in THF (5 mL). The flask was cooled to -78 C. To the solution was added n-butyllithium in hexanes (0.55 mL, 1.37 mmol). The solution was stirred for 15 minutes. To the solution was added zinc(II) chloride in THF (2.74 mL, 1.37 mmol). The solution was immediately allowed to warm to r.t. (using a r.t. water bath) with stirring for 30 min. To the solution was added 2-chloro-4-fluoropyridine (150 mg, 1.14 mmol), then Pd(dppf)Cl2 (42 mg, 0.057 mmol). The vial was placed in a 60 C heating block with stirring for 2.25 h. The reaction solultion was transfered to a 125 mL separatory funnel and was diluted with Et20 (20 mL). The solution was washed with sat. aq. NaHC03 (20 mL). The aq. phase was extracted with EtOAc (25 mL). The combined organics were washed with brine (20 mL); dried over MgS04; filtered; then concentrated in vacuo to afford an orange residue. This material was subjected to silica gel chromatography (hexanes :EtO Ac, 100:0 to 80:20) to afford 2-(4- fluoropyridin-2-yl)-5-methylthiazole as a white solid (54 mg, 24%). 1H-NMR (400MHz, CDC13) delta 8.55 (dd, J=8.2, 5.4 Hz, 1H), 7.91 - 7.82 (m, 1H), 7.62 - 7.56 (m, 1H), 7.02 (ddd, J=8.2, 5.6, 2.5 Hz, 1H), 2.55 (d, J=1.3 Hz, 3H).

Reference： [1]Patent: WO2014/71007,2014,A1 .Location in patent: Page/Page column 46

27
[ 41731-23-1 ]
[ 16063-69-7 ]
[ 1608483-01-7 ]
[ 1608483-02-8 ]

Yield	Reaction Conditions	Operation in experiment
48%; 8%		A dry 25 mL schlenk flask equipped with a stir bar and placed under N2 atmosphere was charged with THF (7 mL) and <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (610 mg, 3.43 mmol). The solution was cooled to -78 C. To the solution was added n- butyllithium in hexanes (1.37 mL, 3.43 mmol) upon which the solution immediately turned dark/golden. The solution was stirred for 5 minutes. To the solution was added zinc(II) chloride in THF (6.85 mL, 3.43 mmol) upon which the solution lightened to a golden color. The solution was immediately warmed to r.t. with a water bath, with stirring for 30 minutes. To the reaction solution was added 2,4,6- trichloropyridine (250 mg, 1.37 mmol) and Pd(dppf)Cl2 (100 mg, 0.137 mmol). The flask was sealed and then was placed in a 60 C oil bath with stirring for 16 h. The reaction solution was trans fered to a 500 mL separatory funnel and was diluted with EtOAc (100 mL), then washed with brine (50 mL). The organic phase was dried over MgS04; filtered; then concentrated in vacuo to afford a dark amber solid. This material was subjected to silica gel chromatography to afford 2-(4,6-dichloropyridin- 2-yl)-5-methylthiazole as a white solid (33 mg, 8%): 1H-NMR (500MHz, CDC13) delta 8.07 (d, J=l .7 Hz, IH), 7.59 (d, J=l .1 Hz, IH), 7.32 (d, J=l .6 Hz, IH), 2.55 (d, J=l .1 Hz, 3H); and 2,2'-(4-chloropyridine-2,6-diyl)bis(5-methylthiazole) as a white solid (160 mg, 48%): 1H-NMR (500MHz, CDC13) 8.10 (s, 2H), 7.60 (d, J=1.3 Hz, 2H), 2.59 - 2.55 (m, 6H).

Reference： [1]Patent: WO2014/71007,2014,A1 .Location in patent: Page/Page column 47

28
[ 41731-23-1 ]
[ 51067-38-0 ]
5-methyl-2-(4-phenoxyphenyl)thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.06 g	With sodium carbonate; In ethanol; toluene; for 6h;Reflux;	To a solution of 4-phenoxyphenylboronic acid (1.05 g, 4.9 mmol) in toluene/ EtOH (6 mL/2 mL) was added <strong>[41731-23-1]2-bromo-5-methylthiazole</strong>(0.87 g, 4.9 mmol) and aq. 2M Na2CO3 (6 mL). The mixture was heated to reflux for 6h, then concentrated. The residue was purified by silica gel column chromatography to afford the title compound (1.06 g) as white solid. 1HNMR (MERCURY 300 MHz, CDCl3) delta 7.86 (d, J = 8.4 Hz, 2H, 2ArH) 7.47 (s, 1H, 1ArH) 7.37 (t, J = 7.8 Hz, 2H, 2ArH) 7.15 (t, J = 7.2 Hz, 1H, 1ArH) 7.04 (t, J = 8.7 Hz, 4H, 4ArH) 2.50 (s, 3H, 1CH3) ESI(m/z) 268 (M+H+)
1.06 g	With sodium carbonate; In ethanol; water; toluene; for 6h;Reflux;	[0185] To a solution of 4-phenoxyphenylboronic acid (1.05g, 4.9 mmol) in toluene/EtOH (6 mL/2 mL) was added<strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (0.87 g, 4.9 mmol) and aq. 2MN a2C03 ( 6 mL). The mixture was heated to reflux for 6 h, thenconcentrated. The residue was purified by silica gel columnchromatography to afford the title compound (1.06 g) aswhite solid.[0186] 1 HNMR (MERCURY 300 MHz, CDCI3 ) o 7.86 ( d,1=8.4 Hz, 2H, 2ArH) 7.47 (s, lH, 1ArH) 7.37 (t, 1=7.8 Hz,2H, 2ArH) 7.15 (t, 1=7.2 Hz, lH, 1ArH)7.04 (t, 1=8.7Hz, 4H,4ArH) 2.50 (s, 3H, 1CH3 )[0187] ESI (m/z) 268 (M+W)

Reference： [1]Patent: EP2786982,2014,A1 .Location in patent: Paragraph 0122-0123
[2]Patent: US2014/323501,2014,A1 .Location in patent: Paragraph 0184; 0185; 0186; 0187

29
[ 41731-23-1 ]
[ 68-12-2 ]
[ 13838-78-3 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of n-BuLi (8.4 ml, 13.48 mmol) in THF (30 mL) was added <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (2.0 g, 11.23 mmol) dropwise under a nitrogen atmosphere at -70 C.; then it was stirred at this temperature for 1.5 h. DMF (1.3 ml, 16.85 mmol) was added dropwise under nitrogen atmosphere at -70 C. The resulting mixture was stirred at this temperature for 1 h. Then the mixture was quenched with aqueous saturated ammonium chloride (5 mL), the mixture was partitioned between ethyl acetate and water. The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give a yellow oil. The yellow oil was dissolved in methanol (15 ml), sodium borohydride (512 mg, 13.48 mmol) was added portionwise under a nitrogen atmosphere at -60 C. The mixture was stirred at this temperature for 1 h. The reaction mixture was quenched with acetone and concentrated. The residue was partitioned between ethyl acetate and water. The organic layers were dried over sodium sulfate, filtered and concentrated, then purified by silica gel chromatography eluting with petroleum/ethyl acetate=3:1 to give thiazol-2-ylmethanol (1.3 g, 90.3%) as brown oil. LCMS MH+ 130.
		(5-methylthiazol-2-yl)methanol To a solution of n-BuLi (8.4 ml, 13.48 mmol) in THF (30 mL) was added 2-bromo-5- methylthiazole(2.0 g, 1 1.23 mmol) dropwise under a nitrogen atmosphere at -70 C ; then it was stirred at this temperature for 1.5 h. DMF (1.3 ml, 16.85 mmol) was added dropwise under nitrogen atmosphere at -70 C. The resulting mixture was stirred at this temperature for 1 h. Then the mixture was quenched with aqueous saturated ammonium chloride (5 mL), the mixture was partitioned between ethyl acetate and water. The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give a yellow oil. The yellow oil was dissolved in methanol (15 ml), sodium borohydride (512 mg, 13.48 mmol) was added portionwise under a nitrogen atmosphere at -60 C. The mixture was stirred at this temperature for 1 h. The reaction mixture was quenched with acetone and concentrated. The residue was partitioned between ethyl acetate and water. The organic layers were dried over sodium sulfate, filtered and concentrated, then purified by silica gel chromatography eluting with petroleum/ ethyl acetate= 3: 1 to give thiazol-2-ylmethanol (1.3 g, 90.3%) as brown oil . LCMS retention time 0.366 min; LCMS MH+ 130.
	With n-butyllithium; In tetrahydrofuran; at -60℃; for 1h;	41-1 (2.00 g, 11.23 mmol) was dissolved in tetrahydrofuran (120 mL), then cooled down to -60C.n-Butyllithium (2.5 mol/L, 4.72 mL) was slowly added dropwise at -60C, and then N,N-dimethylformamide (1.30 mL,16.85 mmol) was added, the reaction was stirred at -60C for 1 hours, and then heated to 25C and stirred for 3 hours.The reaction was quenched by water, and then extracted by dichloromethane (50 mL3), the organic phase was washedwith saturated brine (35 mL2), dried over anhydrous sodium sulfate, then filtered and concentrated in vacuum to givethe compound 41-2. 1H NMR (400MHz, CDCl3) :delta 9. 78 (s, 1H), 7. 68 (s, 1H), 2. 49 (d, J=1. 0 Hz, 3H).

Reference： [1]Patent: US2014/275528,2014,A1 .Location in patent: Paragraph 0281; 0282
[2]Patent: WO2014/143799,2014,A2 .Location in patent: Page/Page column 368
[3]Patent: EP3590942,2020,A1 .Location in patent: Paragraph 0204; 0205; 0206

30
[ 41731-23-1 ]
[ 1206708-88-4 ]

Yield	Reaction Conditions	Operation in experiment
36%	With bromine; In chloroform; acetonitrile; for 16h;Reflux;	Step 1 : To a solution of <strong>[41731-23-1]2-bromo-5-methyl-thiazole</strong> (3.0 g, 16.9 mmol) in a mixture of CHCI3 (30 mL) and CH3CN (30 mL) was added bromine (2.6 mL, 50.6 mmol) and the RM was heated at reflux for 16 h. The RM was quenched with sodium thiosulfate solution and extracted with CH2CI2. The combined organic layers were washed with water and brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by CC (Si02, EtOAc/Hex) to yield 2,4-dibromo-5-methyl-thiazole (1.6 g, 36%).

Reference： [1]Journal of Materials Chemistry C,2015,vol. 3,p. 4156 - 4161
[2]Journal of the American Chemical Society,2015,vol. 137,p. 2738 - 2747
[3]Patent: WO2015/22073,2015,A1 .Location in patent: Page/Page column 108

31
[ 41731-23-1 ]
[ 13808-64-5 ]
C₈H₈BrN₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%		To a solution of 4-bromo-3 -methyl- lH-pyrazole 1 (0.25 g, 1.55 mmol) indimethylformamide (DMF) (30 mL) was added NaH (0.08 g, 3.2 mmol). The mixture was stirred for 0.5 h at room temperature and 2-bromo-5-methyl-l,3-thiazole (0.33 g, 1.86 mmol) was added. The reaction mixture was stirred for 1 h at room temperature. The reaction temperature was raised to 90C and stirred overnight. The reaction was quenched with MeOH and solvent was removed in vacuo. The residue was treated with water and EtOAc. The organic layer was separated and aqueous was extracted with EtOAc. The combined organic phase was dried over Na2S04, filtered, and concentrated to give crude product. The crude product was purified on ISCO columns. Fractions containing pure product were combined and evaporated to give 53 (0.2 g, 50%) as a white solid.

Reference： [1]Patent: WO2015/54283,2015,A1 .Location in patent: Paragraph 00536

32
[ 41731-23-1 ]
(2-pyrazinyl)tributyltin [ No CAS ]
C₈H₇N₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With tetrakis(triphenylphosphine) palladium(0); In toluene; for 15.25h;Inert atmosphere; Reflux;	Example 14a [0247] [0248] Tetrakis(triphenylphosphine)palladium(0) (751 mg, 0.65 mmol) is added, under nitrogen atmosphere, to a solution of 2-(tributylstannyl)pyrazine (2.4 g, 6.5 mmol) and <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (2.3 g, 13.0 mmol), in 40 ml of dry toluene previously degassed bubbling nitrogen for 15 minutes and the reaction is refluxed 15 hours. Solvent is removed, the residue is suspended in Et2O and the precipitate is filtered off. Filtrate is concentrated under reduced pressure and the residue is purified by Silica gel flash cromatography using EtOAc/cyclohexane (from 10:90 to EtOAc 100%) as eluent to obtain the title compound (516 mg, 44% yield). [0249] UPLC-MS (Method 2): Rt=0.92 min [0250] MS (ES+): m/z=178 [M+H]+
44%	With tetrakis(triphenylphosphine) palladium(0); In toluene; for 15h;Inert atmosphere; Reflux;	Tetrakis(triphenylphosphine)palladium(0) (751 mg, 0.65 mmol) is added, under nitrogen atmosphere, to a solution of 2-(tributylstannyl)pyrazine (2.4 g, 6.5 mmol) and 2-bromo-5- methylthiazole (2.3 g, 13.0 mmol), in 40 ml of dry toluene previously degassed bubbling nitrogen for 15 minutes and the reaction is refluxed 15 hours. Solvent is removed, the residue is suspended in Et20 and the precipitate is filtered off. Filtrate is concentrated under reduced pressure and the residue is purified by Silica gel flash cromatography using EtOAc/cyclohexane (from 10:90 to EtOAc 100%) as eluent to obtain the title compound (516 mg, 44% yield). UPLC-MS (Method 2): Rt = 0.92 MS (ES+): m/z = 178 [M+H]+

Reference： [1]Patent: US2015/105397,2015,A1 .Location in patent: Paragraph 0247; 0248; 0249; 0250
[2]Patent: WO2015/55698,2015,A1 .Location in patent: Page/Page column 56

33
[ 41731-23-1 ]
1,3-dimethyl-7-(3-methylbenzyl)-8-(piperidin-4-yloxy)-1H-purine-2,6(3H,7H)-dione hydrogen chloride [ No CAS ]
[ 76-05-1 ]
1,3-dimethyl-7-(3-methylbenzyl)-8-((1-(5-methylthiazol-2-yl)piperidin-4-yl)oxy)-1H-purine-2,6(3H,7H)-dione trifluoroacetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5967 - 5978

34
[ 41731-23-1 ]
[ 1073354-97-8 ]
3-(5-methylthiazol-2-yl)pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); In 1,4-dioxane; water; at 110℃; for 1.5h;Microwave irradiation;	Step 1 : 3-(5-Methylthiazol-2-yl)pyridin-2-amine 2- Aminopyridine-3-boronic acid pinacol ester (200 mg, 0.909 mmol), 2-bromo-5- methylthiazole (147 mg, 0.826 mmol) and potassium phosphate (351 mg, 1.652 mmol) was added to a 2-5 ml microwave vial. 1 ,4-dioxane (3305 muIota), water (826 muIota) and Pd-118 (25.4 mg, 0.041 mmol) was added and the reaction mixture was heated in a microwave reactor at 'very high' absorbance level for 90 minutes at 120C. The reaction mixture was added to water (50 ml) and extracted with EtOAc (50 ml). The organic phase was washed with brine (50 ml) and dried over MgS04. The solid was filtered off, washed with EtOAc and the solvent was concentrated under reduced pressure. The crude residue was purified by flash column chromatography, eluting with a gradient of 0-5% MeOH in DCM using a 12 g silica column, loading with DCM. The appropriate fractions were concentrated under reduced pressure to give the title compound as a light brown solid; LCMS: Rt 0.53 mins; MS m/z 191.7 [M+H]+; Method 2minl_owpHv03. 1H NMR (400 MHz, DMSO-d6) delta 8.05 (1 H, dd), 7.85 (1 H, dd), 7.61 (1 H, d), 7.52 (2H, br s), 6.65 (1 H, q). Aromatic methyl signal believed to be under DMSO solvent peak.

Reference： [1]Patent: WO2015/162456,2015,A1 .Location in patent: Page/Page column 278

35
[ 41731-23-1 ]
[ 1413732-47-4 ]
5-methyl-2-[(trifluoromethyl)thio]thiazole [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 386 - 394

36
[ 41731-23-1 ]
[ 87199-18-6 ]
3-(5-methyl-1,3-thiazol-2-yl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 110℃; for 0.5h;Microwave irradiation;	(3-Hydroxyphenyl) boronic acid (170 mg, 1.235 mmol), 2-bromo-5-methyl- l,3-thiazole (200 mg, 1.123 mmol), K3P04 (481 mg, 2.246 mmol) and Pd(Ph3)4 (131 mg, 0.1 12 mmol) in a mixture 3: 1 of dioxane/ water (12 mL : 4 mL) was heated in MW at 1 10 C for 30 min. The mixture was concentrated under vacuum and NaOH aq solution 1 M and DCM were added. The water was extracted several times with more DCM. The layers were separated. To the aqueous phase HC1 1M aqueous solution was added and the phase was extracted again with more DCM. The combined organics were filtered though a phase separator tube and concentrated in vacuo to give the desired product (190 mg, 0.99 mmol, Yield=75%). LC-MS (ESI): mlz (M+l)+, 191.9.

Reference： [1]Patent: WO2016/4272,2016,A1 .Location in patent: Paragraph 00958

37
[ 79762-54-2 ]
[ 41731-23-1 ]
2-(6-bromo-1H-indazol-1-yl)-5-methylthiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With sodium hydride; In N,N-dimethyl-formamide; at 130℃; for 12h;	The preparation of 2-(6-bromo-lH-indazol-l-yl)-5-methylthiazole was the similar to that of 6-bromo-l-(6-methylpyridin-2-yl)-lH-indazole. 200 mg, as a brown solid, Y: 33%. ESI-MS (M+H)+: 294.0. 1H NMR (400 MHz, CDC13) delta: 8.81 (s, 1H), 8.11 (s, 1H), 7.62 (d, J = 8.5 Hz, 1H), 7.42 (dd, J = 8.5, 1.6 Hz, 1H), 7.26 (s, 1H), 2.48 (d, J = 1.2 Hz, 3H).

Reference： [1]Patent: WO2016/11390,2016,A1 .Location in patent: Page/Page column 215

38
[ 41731-23-1 ]
1-(1-(benzo[d][1,3]dioxol-5-yl)ethyl)piperazine hydrochloride [ No CAS ]
2-(4-(1-(benzo[d][1,3]dioxol-5-yl)ethyl)piperazin-1-yl)-5-methylthiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 16h;	General procedure: To a stirred solution of amine (1 mmol/0.8 to 1 equiv) in dry DMF (5 to 10 mL), chloro compound (1.0 to 1.2 equiv) and potassium carbonate (2 equiv) were added at rt. The resulting mixture was heated at 90 C for 16 h. It was concentrated under vacuum and the resulting residue was diluted with DCM (20 to 50 mL). The DCM layer was washed with water (5 to 10 mL), brine solution (5 to 10 mL), dried over anhydrous Na2SO4 and concentrated under vacuum. The crude products were purified by flash chromatography to afford the desired product.

Reference： [1]Patent: WO2016/30443,2016,A1 .Location in patent: Page/Page column 76-77; 122

39
[ 41731-23-1 ]
[ 935685-88-4 ]
3-fluoro-5-(5-methyl-1,3-thiazol-2-yl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃; for 16h;Inert atmosphere;	Intermediate 25 (15 g, 51 mmol), <strong>[41731-23-1]2-bromo-5-methyl-1,3-thiazole</strong> (5.9 mL, 56 mmol) and potassium carbonate (17.6 g, 127.5 mmol) were dissolved in 4:1 1,4- dioxane/water (200 mL). The solution was with N2 for 10 mm.Tetrakis(triphenylphosphine)palladium(0) (1.2 g, 1.0 mmol) was added and the reaction mixture heated at 80 C for 16 h. After this time the reaction mixture was partitioned between water and EtOAc. The organic phase was separated and the aqueous phase extracted with further EtOAc. The combined organics were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. Thecrude material was purified by Biotage Isolera chromatography (silica gel, eluting with heptanes-EtOAc, 1:0 to 4:1). The product containing fractions were combined and triturated with heptane and the precipitate collected and dried by vacuum filtration. The mother liqueur and mixed fractions were combined and concentrated. The residue was re-purified by Biotage Isolera chromatography (silica gel, eluting with heptane-EtOAc, 1:0 to 4:1). The two batches were combined to afford 7.06 g (59% yield) of the title compound as white powder.1H NMR (250 MHz, Chloroform-d): 6 [ppm] 7.96 (t, J = 1.4 Hz, 1H), 7.86 (ddd, J =9.2, 2.4, 1.6 Hz, 1H), 7.57 (d, J = 1.1 Hz, 1H), 7.35 (ddd, J = 7.7, 2.5, 1.3 Hz, 1H),2.55 (d, J = 1.1 Hz, 3H).LCMS (Analytical Method A) Rt = 1.26 mm, MS (ESipos): m/z = 218.85 (M+H)+.

Reference： [1]Patent: WO2016/91776,2016,A1 .Location in patent: Page/Page column 207; 208

40
[ 41731-23-1 ]
methyl 3-[(3R)-tetrahydrofuran-3-yl]oxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [ No CAS ]
methyl 3-(5-methyl-1,3-thiazol-2-yl)-5-[(3R)-tetrahydrofuran-3-yloxy]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere;	Intermediate 8 (5.2 g, 14.9 mmol), <strong>[41731-23-1]2-bromo-5-methyl-1,3-thiazole</strong> (1.87 mL, 17.9 mmol) and cesium carbonate (12.2 g, 37.3 mmol) were dissolved in 4:1 1,4- dioxane/water (75 mL). The solution was degassed with a stream of nitrogen for 10 mi Tetrakis(triphenylphosphine)palladium(0) (517.7 mg, 0.45 mmol) was addedand the reaction mixture heated at 100 C overnight. The reaction mixture was diluted with water (100 mL) and extracted with DCM (2 x 100 mL). The combined organics were dried (MgSO4), filtered and concentrated under reduced pressure. The crude material was purified by Biotage IsoleraTM chromatography (eluting with 1 - 40 % EtOAc in heptane on a 100 g KP-Si02 column) to give the title compound3.06 g (64 % yield) as a yellow solid.1H NMR (250 MHz, Chloroform-d): 6 [ppm] 8.11 (t, J = 1.4 Hz, 1H), 7.67 - 7.63 (m, 1H), 7.55 (dd, J = 2.5, 1.4 Hz, 1H), 7.52 (d, J = 1.2 Hz, 1H), 5.07 (td, J = 4.1, 2.2 Hz, 1H), 4.11 - 3.86 (m, 7H), 2.53 (d, J = 1.1 Hz, 3H), 2.35 -2.09 (m, 2H).LCMS (Analytical Method A) Rt = 1.34 mm, MS (ESIpos): m/z = 320 (M+H).

Reference： [1]Patent: WO2016/91776,2016,A1 .Location in patent: Page/Page column 146

41
[ 41731-23-1 ]
(3-[(2-methylpyridin-4-yl)oxy]-5-[(1R)-1-(2-methylpyrimidin-5-yl)ethyl]carbamoyl}phenyl)boronic acid [ No CAS ]
3-[(2-methylpyridin-4-yl)oxy]-N-[(1R)-1-(2-methylpyrimidin-5-yl)ethyl]-5-(5-methyl-1,3-thiazol-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In tetrahydrofuran; water; for 2h;Reflux;	(3-[(2-methylpyridin-4-yl)oxy]-5-f[(1 R)-1 -(2-methylpyrimidin-5-yl)ethyl]carbamoylphenyl)boronic acid (96 mg, 0.24 mmol) and <strong>[41731-23-1]2-bromo-5-methyl-1,3-thiazole</strong> (65 mg, 0.37 mmol) were dissolved in 1M K2C03 aqueous solution (0.59mL) and THF (4 mL). Pd(dppf)C12CH2C12 (30 mg, 0.04 mmol) was added and the reaction mixture heated to reflux for 2 hours. The reaction mixture was concentrated under reduced pressure. Crude material was purified by preparative HPLC (method 2, rt: 1 .03 mm) to afford the title compound 27 mg (25% yield).1H NMR (300MHz, DMSO-d6) 6 [ppm] 1.54 (d, J=7.16 Hz, 3 H) 2.43 (5, 3 H) 2.59 (5, 3H) 5.17 (5, 1 H) 6.84 (dd, J=5.65, 2.45 Hz, 1 H) 6.91 (d, J=2.26 Hz, 1 H) 7.66 (d,J=1.13 Hz, 1 H) 7.71 - 7.78 (m, 2 H) 8.24 (s, 1 H) 8.37 (d, J=5.65 Hz, 1 H) 8.72 (s, 2 H) 9.14 (d, J=7.35 Hz, 1 H).

Reference： [1]Patent: WO2016/91776,2016,A1 .Location in patent: Page/Page column 455; 456

42
[ 41731-23-1 ]
3-(2-methoxyethoxy)-N-[(1R)-1-(2-methylpyrimidin-5-yl)ethyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide [ No CAS ]
3-(2-methoxyethoxy)-N-[(1R)-1-(2-methylpyrimidin-5-yl)ethyl]-5-(5-methyl-1,3-thiazol-2-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In tetrahydrofuran;Reflux;	3-(2-Methoxyethoxy)-N-[(1 R)-1 -(2-methylpyrimidin-5-yl)ethyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (150 mg, 0.34 mmol) and 2-bromo- 5-methyl-1,3-thiazole (91 mg, 0.51 mmol) were dissolved in 1M K2C03 aqueous solution (0.84 mL) and THF. Pd(dppf)C12CH2C12 (42 mg, 0.05 mmol) was added and the reaction mixture heated to reflux overnight. The reaction mixture was concentrated under reduced pressure. Crude material was purified by preparative HPLC (Method 1) to afford the title compound 80 mg (57% yield).1H NMR (300MHz, DMSO-d6) 6 [ppm] 1.54 (d, J=7.16 Hz, 3 H) 2.59 (5, 3 H) 3.32 (5, 3 H) 3.69 (dd, J=5.18, 3.67 Hz, 2 H) 4.19 - 4.25 (m, 2 H) 5.17 (t, J=7.16 Hz, 1 H) 7.50- 7.56 (m, 2 H) 7.64 (d, J=1.32 Hz, 1 H) 7.91 (5, 1 H) 8.72 (5, 2 H) 9.05 (d, J=7.54 Hz, 1 H).

Reference： [1]Patent: WO2016/91776,2016,A1 .Location in patent: Page/Page column 473; 474

43
[ 41731-23-1 ]
[ 1004294-79-4 ]
methyl 3-hydroxy-5-(5-methyl-1,3-thiazol-2-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In tetrahydrofuran; water; at 90℃; for 17h;Inert atmosphere;	Intermediate 2 (1.0 g, 3.60 mmo[) and 2-bromo-5-methy[-1,3-thiazo[e (0.451 mL, 4.32 mmo[) were dissolved in 1M K2C03 aqueous solution (8.63 mL) and THF (58.7 mL). The solution was degassed with a stream of nitrogen for 10 minutes, [1,1- Bis(diphenylphosphino)ferrocene] palladium(II) dichloride (395.3 mg, 0.539 mmol)was added and the reaction mixture heated at 90 C for 17 h until reaction completion (monitored by TLC). The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (3 x 100 mL). The combined organics were dried (over MgSO4) and concentrated under reduced pressure. Crude material was purified by Biotage IsoleraTM chromatography (eluting with 12 - 80 % EtOAc inheptane on a 25 g pre-packed KP-Si02 column) to give 359.7 mg (40% yield) of the title compound as an off-white powder.1H NMR (250 MHz, Chloroform-d): 6 [ppm] 8.06 (t, J = 1.4 Hz, 1H), 7.67 - 7.62 (m,1H), 7.54 (dd, J = 2.5, 1.4 Hz, 1H), 7.52 (d, J = 1.1 Hz, 1H), 5.84 (5, 2H), 3.93 (5,3H), 2.53 (d, J = 1.1 Hz, 3H).

Reference： [1]Patent: WO2016/91776,2016,A1 .Location in patent: Page/Page column 141

44
[ 41731-23-1 ]
(R)-4-((R)-1-((1-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one [ No CAS ]
(R)-4-((R)-1-((1-cyclopropyl-5-(5-methylthiazol-2-yl)-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37.8%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 140℃; for 0.25h;Microwave irradiation; Inert atmosphere; Sealed tube;	To a microwave tube equipped with a stifling bar, (R)-4-((R)-1-((1-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one (120 mg, 0.292 mmol), <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (103.9 mg, 0.584 mmol), 1,2-dimethoxyethane (2 mL), 1 N Na2CO3 aqueous solution (0.96 mL, 0.96 mmol) were added, the mixture was bubbled N2 for 5 minutes before Pd(PPh3)4 (33.7 mg, 0.029 mmol) was added. The tube was sealed and heated in microwave at 140 C. for 15 minutes. DCM (200 mL) was added and the resulting mixture was washed with saturated NaHCO3 aqueous solution (20 mL×4), brine (20 mL×1), dried over anhydrous Na2SO4, filtered, removed solvents in vacuo. The resulting residue was passed a ISCO silica gel column (MeOH:DCM=5:95) to give off-white solids, 42.2 mg (yield 37.8%).

Reference： [1]Patent: KR2016/37198,2016,A .Location in patent: Paragraph 2109-2111

45
[ 41731-23-1 ]
methyl (4aR)-6-((3,4-difluorophenyl)sulfonyl)-1-(4-fluorophenyl)-4,4a,5,6,7,8-hexahydro-1H-pyrazolo[3,4-g]isoquinoline-4a-carboxylate [ No CAS ]
((4aR)-6-((3,4-difluorophenyl)sulfonyl)-1-(4-fluorophenyl)-4,4a,5,6,7,8-hexahydro-1H-pyrazolo[3,4-g]isoquinolin-4a-yl)(5-methylthiazol-2-yl)methanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 3405 - 3421

46
[ 41731-23-1 ]
methyl (4aR)-6-((3,4-dichlorophenyl)sulfonyl)-1-(4-fluorophenyl)-4,4a,5,6,7,8-hexahydro-1H-pyrazolo[3,4-g]-isoquinoline-4a-carboxylate [ No CAS ]
((4aR)-6-((3,4-dichlorophenyl)sulfonyl)-1-(4-fluorophenyl)-4,4a,5,6,7,8-hexahydro-1H-pyrazolo[3,4-g]isoquinolin-4a-yl)(5-methylthiazol-2-yl)methanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 3405 - 3421

47
[ 41731-23-1 ]
methyl (4aR)-1-(4-fluorophenyl)-6-((3-(trifluoromethyl)-phenyl)sulfonyl)-4,4a,5,6,7,8-hexahydro-1H-pyrazolo[3,4-g]-isoquinoline-4a-carboxylate [ No CAS ]
((4aR)-1-(4-fluorophenyl)-6-((3-(trifluoromethyl)phenyl)-sulfonyl)-4,4a,5,6,7,8-hexahydro-1H-pyrazolo[3,4-g]-isoquinolin-4a-yl)(5-methylthiazol-2-yl)methanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 3405 - 3421

48
[ 41731-23-1 ]
[ 4105-21-9 ]
5-methyl-2-(2-phenylimidazo[1,2-a]pyridin-3-yl)thiazole [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 5318 - 5324

49
[ 41731-23-1 ]
(R)-(3-(4-ethoxy-3-methyl-3-(methylsulfonyl)-4-oxobutyl)-4-oxo-3,4-dihydroquinazolin-7-yl)boronicacid [ No CAS ]
[ 73183-34-3 ]
(R)-ethyl 2-methyl-2-(methylsulfonyl)-4-(5-(5-methylthiophen-2-yl)-1-oxoisoindolin-2-yl)butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		(Intermediate 15) (200 mg, 0.478 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1 ,3,2- dioxaborolane) (182 mg, 0.717 mmol), PdC (dppf) (35 mg, 0.048 mmol) and potassium acetate (141 mg, 1 .434 mmol) was added to 1 ,2-dimethoxyethane (3 ml_). The resulting solution was stirred at 80 C for 3 hr and filtered through a pad of celite. The solvent was removed, the residue was dissolved in acetonitrile (2.4 ml_) and water (0.4 ml_) and 2- bromo-5-methylthiophene (102 mg, 0.574 mmol), PdC (dppf) (70 mg, 0.096 mmol) and potassium carbonate (132 mg, 0.956 mmol) were added. The resulting solution was stirred at 80 C for 1 hr. After completion, the solvent was removed and the crude product was purified by silica gel chromatography (EtOAc/hexanes: 0-100%) to afford (R)-ethyl 2- methyl-2-(methylsulfonyl)-4-(5-(5-methylthiophen-2-yl)-1 -oxoisoindolin-2-yl)butanoate (153 mg, 0.351 mmol, 74 % yield). LCMS: [M+H] 436.2. NMR (CHLOROFORM-d) delta: ppm 7.75 - 7.84 (m, 1 H), 7.58 - 7.70 (m, 2 H), 7.24 (d, J = 3.5 Hz, 1 H), 6.79 (dd, J = 3.5, 1 .0 Hz, 1 H), 4.26 - 4.54 (m, 2 H), 3.81 - 4.22 (m, 3 H), 3.55 - 3.76 (m, 1 H), 2.97 - 3.15 (m, 3 H), 2.72 (dt, J = 13.5, 8.0 Hz, 1 H), 2.47 - 2.63 (m, 3 H), 2.18 - 2.36 (m, 1 H), 1 .76 - 1 .89 (m, 3 H), 1 .62 (br. s., 1 H), 1 .21 (t, J = 7.1 Hz, 3 H).

Reference： [1]Patent: WO2017/98440,2017,A1 .Location in patent: Page/Page column 265

50
[ 41731-23-1 ]
(R)-ethyl 2-methyl-2-(methylsulfonyl)-4-(4-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-3(4H)-yl)butanoate [ No CAS ]
(R)-ethyl2-methyl-2-(methylsulfonyl)-4-(6-(5-methylthiazol-2-yl)-1-oxoisoquinolin-2(1H)-yl)butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In water; acetonitrile; at 80℃;Inert atmosphere;	PdCI2(dppf) (92 mg, 0.126 mmol) was added to a solution of (R)-ethyl 2-methyl-2- (methylsulfonyl)-4-(1 -oxo-6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)isoquinolin- 2(1 H)-yl)butanoate (Intermediate 20) (400 mg, 0.838 mmol), <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (373 mg, 2.095 mmol) and potassium carbonate (232 mg, 1 .676 mmol) in acetonitrile (15 ml_) and water (3 ml_) at room temperature under a nitrogen atomsphere. The reaction mixture was stirred at 80 C overnight and was combined with another batch and the solution was concentrated and the residue was purified by silica gel chromatography (EtOAc/petroleum ether: 1/1) to give (R)-ethyl 2-methyl-2-(methylsulfonyl)-4-(6-(5- methylthiazol-2-yl)-1 -oxoisoquinolin-2(1 H)-yl)butanoate (222 mg, 0.495 mmol, 59 % yield) as a yellow oil. LCMS: [M+H] 449.0.

Reference： [1]Patent: WO2017/98440,2017,A1 .Location in patent: Page/Page column 206

51
[ 41731-23-1 ]
3-bromo-5-chloro-4-fluorophenol [ No CAS ]
2-(3-bromo-5-chloro-4-fluorophenoxy)-5-methylthiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 150℃; for 0.5h;Microwave irradiation;	A mixture of3-brorno-5-chioro-4-fiuorophenol (500 mg, 2.218 mrnol), 2-brorno- 5-methyithiazole (434 mg,2.440 mmol) and Cs2CO3 (1.08 g, 3.33 mmoi) in NMP (6 rnL) was stirred under microwave irradiation at 150C for 30 mm. The mixture was extracted with EtOAc (20 mnLx3), and the organic layer was washed with water (15 mE). The organic layer was dried (Na2SO4) andconcentrated in vacuo. The residue was purified by reverse phase HPLC on a GILSON 281 instrument fitted with a Phenomenex Synergi C18 (25021.2 mm4 lim) column using water (0.2% TFA) and ACN as eluenis (Mobile phase A: water (0. 2% TFA). Mobile phase B: ACN, Detector wavelength: 220 nm) followed by concentration in vacuo to obtain the title compound.?H NMR (400 MHz, CDC13) 5 7.43 (dd. J=489, 2.93 Hz, 1 H) 7.34 (dd, J=5.48, 2.74 Hz, I H)6.91 (s, 1 H) 2.38 (s, 3 Fl).

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 96 - 101
[2]Patent: WO2017/205193,2017,A1 .Location in patent: Page/Page column 44

52
[ 41731-23-1 ]
3-bromo-4-fluoro-5-methoxyphenol [ No CAS ]
2-(3-bromo-4-fluoro-5-methoxyphenoxy)-5-methylthiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 150℃; for 3h;Sealed tube; Microwave irradiation;	To a soln. of 3-bromo-4-fluoro-5-methoxyphenol (663 rng, 3 mmoi) and 2-bromo- 5-methylthiazole (587 mg,3.3 rnrnoi) in NMI (5 inL) was added Cs2CO3 (1.20 g, 3.6 mrnol) in one portion. The reactionvessel was sealed and heated by microwave irradiation at 150C for 3 h. The reaction mixture was poured into cold water (50 mL) and extracted with DCM (3 x 10 mL). The combined layers were combined and washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (PE:EtOAc=i 0:1) to afford the title compound. ?H NMR (400 MHz. CDC13) 13 ppm 7.06 (dd, 1=4.70, 274 Hz, I H) 6.82-6.92 (in, 2 H) 3.89 (s, 3H)238(s,3H).

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 96 - 101
[2]Patent: WO2017/205193,2017,A1 .Location in patent: Page/Page column 67

53
[ 41731-23-1 ]
[ 1364606-67-6 ]
2-(5-bromo-4-fluoro-2-methoxyphenoxy)-5-methylthiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 18h;	A mixture of2-hromo-5-methylthiazole (300 mg, 1.68 mnmoi). 5-bromo-4-fiuoro-2-mnethoxvphenoi (410 111g.1.85 rnmoi) and K2C03 (466 rng, 3.37 mmol) in DMF (10 rnL) was stirred at 120C for 18 h.The mixture was diluted with water (200 mnL) and extracted with EtOAc 3 x 20 mL). The A mixture of2-hromo-5-methylthiazole (300 mg, 1.68 mnmoi). 5-bromo-4-fiuoro-2-mnethoxvphenoi (410 111g.1.85 rnmoi) and K2C03 (466 rng, 3.37 mmol) in DMF (10 rnL) was stirred at 120C for 18 h.The mixture was diluted with water (200 mnL) and extracted with EtOAc 3 x 20 mL). The

Reference： [1]Patent: WO2017/205193,2017,A1 .Location in patent: Page/Page column 53; 54

54
[ 41731-23-1 ]
3-bromo-5-(difluoromethyl)-4-fluorophenol [ No CAS ]
2-(3-bromo-5-(difluoromethyl)-4-fluorophenoxy)-5-methylthiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 160℃; for 0.5h;Microwave irradiation;	A mixture of 2-bromo-5-methvithiazoie (300 mg. 1 68 mmoi), 3-bromo-5-(difiuoromethyi)-4- fluorophenol(487 mg, 2.02 mmol) and CsCO3 (1.09 g, 3.37 mmol) in DMF (5 mE) was irradiated bynicrowave at 160C for 0.5 h. The mixture was diluted with waler (20 mE), and extracted withEtOAc (2 xi 0 niL). The organic layer was collected, washed with brine, dried over anhydrousNa2SO, filtered and concentrated in vacno. The residue was further purified by reverse phase1-IPEC on a GIESON 281 instrument fitted with a Phenomenex Synergi C 18 (25() x 21.2 mm x 4lIm) using water (0.2% Formic acid) and MeCN as eluents (Mobile phase A: water (0.2% Formic acid), Mobile phase B: CH3CN, Detective wavelength: 220 nm), followed by concentration (below 50 C) to afford the title compound

Reference： [1]Patent: WO2017/205193,2017,A1 .Location in patent: Page/Page column 69

55
[ 41731-23-1 ]
2-(difluoromethoxy)-7-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline [ No CAS ]
2-(2-(difluoromethoxy)-7-methylquinoxalin-5-yl)-5-methylthiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16.1%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In N,N-dimethyl-formamide; at 90℃; for 0.5h;Inert atmosphere; Sealed tube; Microwave irradiation;	Intermediate I-1 (17.1 mg, 0.051 mmol) and <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (13.59 mg, 0.076 mmol) were dissolved in DMF (509 muL). PdCl2(dppf)-CH2Cl2 (2.493 mg, 3.05 mumol) was added and the reaction mixture was degassed by bubbling with argon for 15 minutes. Sodium carbonate (2 M, 30.5 muL, 0.061 mmol) was added and the reaction mixture was degassed for 5 minutes, then sealed and heated to 90 C in the microwave for 30 minutes. The reaction mixture was diluted with DMF and purified by preparative HPLC (Method D, 45 to 85% B in 10 minutes) then repurified by preparative HPLC (Method D, 40 to 75% B in 20 minutes) to give Example 4 (2.6 mg, 0.00821 mmol, 16.1%): 1H NMR (500MHz, METHANOL-d4) delta 8.65 (s, 1H), 8.44 (d, J=1.7 Hz, 1H), 7.85-7.52 (m, 3H), 2.64 (s, 3H), 2.58 (s, 3H); LC-MS: Method H, RT = 1.12 min, MS (ESI) m/z: 307.9 (M+H)+ Analytical HPLC Method B: 97.0% purity.

Reference： [1]Patent: WO2018/13772,2018,A1 .Location in patent: Page/Page column 66-67

56
[ 41731-23-1 ]
[ 18162-48-6 ]
tert-butyl-dimethyl-(5-methylthiazol-2-yl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.1 g		To a stirred solution of <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (1.00 g, 5.62 mmol ) in THF (20 mL) was added w-butyllithium solution (2.7 mL, 6.74 mmol, hexane solution) slowly at -70 C and the mixture was stirred for 0.5 hr at -70 C. Then to the resulting mixture was added tert- butyldimethylchlorosilane (1.02 g, 6.74 mmol) slowly. After being warmed to 20 C and stirred for another 2 hrs, the reaction mixture was diluted with saturated NH4C1 solution and extracted with EA (30 mL) for three times. The combined organic phase was washed with brine (20 mL), then dried over anhydrous Na2S04, concentrated in vacuo and purified by the flash column chromatography (eluting with PE:EA=50: 1, v:v) to give ieri-butyl-dimethyl-(5-methylthiazol-2- yl)silane (1.10 g) as a yellow liquid.

Reference： [1]Patent: WO2018/83081,2018,A1 .Location in patent: Page/Page column 68; 69

57
[ 41731-23-1 ]
C₂₃H₂₅BN₂O₃ [ No CAS ]
5-methyl-2-(4-[4'-methyl-(3,3'-bipyridine)-2-yl]oxy}phenyl)thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); caesium carbonate; In 1,4-dioxane; at 120℃; for 0.5h;Microwave irradiation;	[0985] A suspension of compound (1-427) (50.0 mg, 0.129 mmol), <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (34.4 mg, 0.193 mmol),(A-taPhos)2PdCl2 (4.6 mg, 6.5 mmomicronl) and cesium carbonate (83.9 mg, 0.258 mmol) in 1,4-dioxane (1.0 mL) was stirredunder microwave irradiation at 120C for 30 min. Water was added to the reaction mixture, and the mixture was extractedwith ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydroussodium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silicagel column chromatography (n-hexane:ethyl acetate = 50:50 ? 0:100) to give compound (I-428) (yield 7.8 mg, 17%) as a colorless oil
17%	With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); caesium carbonate; In 1,4-dioxane; at 120℃; for 0.5h;Microwave irradiation;	Compound (I-427) (50.0 mg, 0.129 mmol),2-Bromo-5-methylthiazole(34.4 mg, 0.193 mmol),(A-taPhos) 2 PdCl2 (4.6 mg, 6.5 mumol)And cesium carbonate (83.9 mg, 0.258 mmol)Of 1,4-dioxane (1.0 mL)Under microwave irradiation,Followed by stirring at 120 C. for 30 minutes. Water was added to the reaction solution,And extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and filtered. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 50: 50 ? 0: 100) to giveTo obtain a compound (I-428) (yield 7.8 mg, yield 17%) as a colorless oil.

Reference： [1]Patent: EP3351533,2018,A1 .Location in patent: Paragraph 0983; 0985
[2]Patent: JP2018/145180,2018,A .Location in patent: Paragraph 0892; 0893; 0894

58
[ 41731-23-1 ]
2-[[4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridin-1-yl]methoxy]ethyltrimethylsilane [ No CAS ]
2-[[4-chloro-3-(5-methylthiazol-2-yl)pyrrolo[2,3-b]pyridin-1-yl]methoxy]ethyltrimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.4%	With tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; water; at 80℃;Inert atmosphere;	A mixture of 2-[[4-chloro-3-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridin-1 -yl]methoxy]ethyl-trimethyl-silane (P15) (4 .00 g, 9.78 mmol), 2- bromo-5-methyl-thiazole (1.15 ml, 11.74 mmol) and tris(dibenzylideneacetone)dipalladium (0) (447.99 mg, 0.49 mmol) was equally separated between 6 flasks. Each flask was purged and evacuated with nitrogen before a degassed solution of 1,4-Dioxane (3 ml) and water (1 ml) was added. The resulting solutions were heated to 80 00 overnight. Further 2-bromo-5- methyl-thiazole (0.479 ml, 4.89 mmol) was added and the reaction mixtures were stirred overnight. The mixtures were allowed to cool to room temperature before being combined and filtered through celite. The liquors were concentrated under reduced pressure and the resulting residue was dissolved in DCM. The organics were washed with water. The aqueous layer was further extracted with DCM (x 2). The organics were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The obtained residue was chromatographed (Si02, 0-60% EtOAc: isohexane) to afford 2-[[4-chloro-3-(5-methylthiazol- 2-yl)pyrrolo[2,3-b]pyridin-1-yl]methoxy]ethyl-trimethyl-silane (P24) (1.8 g, 4.74 mmol, 48.4 % yield) as a yellow oil which solidified upon standing, LCMS ES 380, 382 [M+H], Rt = 1.70 mins (Generic Basic Method).

Reference： [1]Patent: WO2019/34890,2019,A1 .Location in patent: Paragraph 00153; 00182

59
[ 41731-23-1 ]
[ 33630-99-8 ]
C₉H₉N₃OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21.25%	With copper(l) iodide; potassium carbonate; 2,3-butane diamine; In 1,4-dioxane; at 110℃; for 16h;Inert atmosphere;	To a solution of 28 (1 g, 9.08 mmol, 1 eq) and 28.1 (1.94 g, 10.90 mmol, 1.2 eq) in 1,4-dioxane (10 mE) was added potassium carbonate (2.50 g, 18.16 mmol, 2.0 eq) and degassed with argon for 15 mm. Copper iodide (0.345 g, 1.81 mmol, 0.2 eq) and 1,2-dimethylethylenediamine (0.320 g, 3.63 mmol, 0.4 eq) was added and reaction mixture again degassed with argon for 5 mm followed by heating at 1100 C. for 16 h. After completion of reaction, reaction mixture was cooled to room temperature, transferred into water and product was extracted with ethyl acetate. Organic layer was combined, washed with brine solution, dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was further purified by column chromatography and compound was eluted in 1.2% methanol in dichloromethane to obtain pure 28.2 (0.400 g, 2 1.25%). MS(ES): mlz 208.25 [M+H].

Reference： [1]Patent: US2019/31664,2019,A1 .Location in patent: Paragraph 0769; 0770; 0771

60
[ 41731-23-1 ]
[ 126747-14-6 ]
2-(4-cyanophenyl)-5-methylthiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 15h;Reflux; Inert atmosphere;	A suspension of <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (17, 2.01 g, 11.3 mmol, 1.00 equiv), pcyanophenylboronic acid (1.8259 g, 12.4 mmol, 1.10 equiv), Pd(PPh3)4 (774.2 mg, 0.676 mmol, 0.06 equiv), and K2CO3 (6.3399 g, 45.9 mmol, 4.07 equiv) in THF (40 mL) and water (20 mL) was refluxed for 15 h under a N2 atmosphere with vigorous stirring. The reaction was quenched by 3 mol dm-3 HCl aq., and the resultant mixture was extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4, the drying agent filtered off, and evaporated. The residue was purified by flash column chromatography on silica gel using ethyl acetate/hexane (3% to 8 %) as the eluent, to give 1.6136 g (8.06 mmol) of 2-(4-cyanophenyl)-5-methylthiazole (18) as a white solid in 71% yield.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 2161 - 2169

61
[ 41731-23-1 ]
[ 87199-17-5 ]
[ 1344734-15-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 2h;Inert atmosphere;	[0233] To a solution of 2-bromo-5-methyl-l,3-thiazole (300 mg, 1.68 mmol, 1.0 equiv) in a mixture of dioxane/water (50/10 mL) were added Pd(dppf)Cl2.CH2Cl2 (138 mg, 0.17 mmol, 0.1 equiv) and potassium carbonate (465 mg, 3.36 mmol, 2.00 equiv) under nitrogen atmosphere. The mixture was stirred at 80 C for 2 h, cooled to r.t, and added water (60 mL). The aqueous layer was extracted with ethyl acetate (30 mL) three times. The combined organic layers were dried over Na2S04, concentrated under reduced pressure, and purified by silica gel column with ethyl acetate/petroleum ether (1/10) to give 330 mg (96%) of 4-(5- methyl-l,3-thiazol-2-yl)benzaldehyde as a yellow solid. LRMS (ES) m/z 204 (M+H).

Reference： [1]Patent: WO2020/5888,2020,A1 .Location in patent: Paragraph 0233

62
[ 41731-23-1 ]
[ 101385-93-7 ]
C₁₃H₂₀N₂O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%		A solution of <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (1.0 g, 5.59 mmol) in THF (20 mL) under a N2 atmosphere was treated with nBuLi (2.7 mL, 6.70 mmol) dropwise at -78C, and the resulting reaction mixture was stirred at -78C for 1 h. A solution of tert-butyl 3-oxopyrrolidine-l-carboxylate (1.2 g, 6.70 mmol) in THF (10 mL) was then added to the reaction mixture dropwise at -78 C. The reaction mixture was then allowed to warm to room temperature, and was stirred at room temperature for 3 h. The mixture was diluted with saturated aqueous NH4Cl (40 mL), and extracted with EtOAc (30 mL x 3). The combined organic layers were washed with brine (20 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE : EtOAc = 10 : 1 to EtOAc) to give 1984-A (760 mg, 48%) as a light yellow solid. MS 285.2 [M+H]+.

Reference： [1]Patent: WO2020/14605,2020,A1 .Location in patent: Paragraph 00148

63
[ 41731-23-1 ]
2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)pyrrolidine [ No CAS ]
2-(4-((2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyrrolidin-1-yl)methyl)phenyl)-5-methylthiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
115 mg	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere;	To a stirred solution of <strong>[41731-23-1]2-bromo-5-methylthiazole</strong> (200 mg, 1.12 mmol) and intermediate 34 (709 mg, 1.68 mmol) in dry dioxane (2 ml_), water (0.3 mL) and cesium carbonate (728 mg, 2.24 mmol) were added at RT. The resulting reaction mixture was flushed with nitrogen for 10 minutes before the addition of tetrakis(triphenylphosphine)paliadium(0) (25 mg, 0.02 mmol). The reaction mixture was heated at 100 C overnight. It was filtered through celite pad and the filtrate was concentrated under vacuum. The resuting crude product was purified by prep HPLC (method A) to afford the title compound. Yield: 26% (1 15 mg, brown gummy solid). 1H NMR (400 MHz, DMSO -<): d 7.80 (d, J = 8.0 Hz, 2H), 7.57 (d, J = 0.8 Hz, 1 H), 7.34 (d, J = 8.0 Hz, 2H), 6.92-6.88 (m, 2H), 6.81 (d, J = 8.0 Hz, 2H), 4.21 (s, 4H), 3.71 (d, J = 13.6 Hz, 1 H), 3.32-3.09 (m, 1 H), 2.98 (d, J = 13.6 Hz, 1 H), 2.94 (t, J = 2.4 Hz, 1 H), 2.48 (s, 3H), 2.15-2.08 (m, 2H), 1 .78-1.71 (m, 2H), 1.58-1.54 (m, 1 H). LCMS: (Method A) 393.1 (M+H), Rt. 1.73 min, 98.44% (Max). HPLC: (Method A) Rt. 3.34 min, 97.87% (Max), 96.31 % (220 nm).

Reference： [1]Patent: WO2020/39027,2020,A1 .Location in patent: Page/Page column 232

64
[ 41731-23-1 ]
[ 59016-93-2 ]
(4-(5-methyl-1,3-thiazol-2-yl)phenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A) (4-(5-methyl-1,3-thiazol-2-yl)phenyl)methanol The title compound was obtained from (4-(hydroxymethyl)phenyl)boronic acid and <strong>[41731-23-1]2-bromo-5-methyl-1,3-thiazole</strong> by a method similar to that in step F of Example 1. MS: [M+H]+ 206.1.

Reference： [1]Patent: EP3643718,2020,A1

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[ CAS No. 41731-23-1 ]

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[ 41731-23-1 ] Synthesis Path-Upstream 1~7

[ 41731-23-1 ] Synthesis Path-Downstream 1~64

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Bromides

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Thiazoles

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