[ CAS No. 91872-10-5 ] {[proInfo.proName]}

Name: 91872-10-5|3,5-Dibromo-6-methyl-2-pyridinamine|98%
Brand: Ambeed
SKU: A741853
Price: 5.0 USD
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Quality Control of [ 91872-10-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 91872-10-5 ]

CAS No. :	91872-10-5	MDL No. :	MFCD00068229
Formula :	C₆H₆Br₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BLUYMDMBXIMIGK-UHFFFAOYSA-N
M.W :	265.93	Pubchem ID :	522994
Synonyms :

Calculated chemistry of [ 91872-10-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	49.01
TPSA :	38.91 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) :	-6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.99
Log Po/w (XLOGP3) :	2.29
Log Po/w (WLOGP) :	2.51
Log Po/w (MLOGP) :	2.08
Log Po/w (SILICOS-IT) :	2.45
Consensus Log Po/w :	2.26

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.38
Solubility :	0.112 mg/ml ; 0.000421 mol/l
Class :	Soluble
Log S (Ali) :	-2.74
Solubility :	0.479 mg/ml ; 0.0018 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.76
Solubility :	0.0463 mg/ml ; 0.000174 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.72

Safety of [ 91872-10-5 ]

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 [ 91872-10-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 91872-10-5 ]
Downstream synthetic route of [ 91872-10-5 ]

[ 91872-10-5 ] Synthesis Path-Upstream 1~9

1
[ 1824-81-3 ]
[ 42753-71-9 ]
[ 91872-10-5 ]

Reference： [1] Heterocycles, 1994, vol. 38, # 3, p. 529 - 540
[2] Russian Journal of Applied Chemistry, 2005, vol. 78, # 5, p. 787 - 790

2
[ 1824-81-3 ]
[ 42753-71-9 ]
[ 91872-10-5 ]
[ 126325-46-0 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374
[2] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374

3
[ 1824-81-3 ]
[ 91872-10-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 2987 - 2991
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 20, p. 5533 - 5539
[3] Journal of the American Chemical Society, 1949, vol. 71, p. 1186,1191

4
[ 5327-33-3 ]
[ 91872-10-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 173 - 178

5
[ 1824-81-3 ]
[ 42753-71-9 ]
[ 91872-10-5 ]

Reference： [1] Heterocycles, 1994, vol. 38, # 3, p. 529 - 540
[2] Russian Journal of Applied Chemistry, 2005, vol. 78, # 5, p. 787 - 790

6
[ 1824-81-3 ]
[ 42753-71-9 ]
[ 91872-10-5 ]
[ 126325-46-0 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374
[2] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374

7
[ 91872-10-5 ]
[ 38749-87-0 ]

Yield	Reaction Conditions	Operation in experiment
42%	With tert.-butylnitrite In tetrahydrofuran for 2 h; Heating / reflux	To a solution of 3,5-dibromo-6-methyl-pyridin-2-ylamine (2.0 g, 7.5 mmol) in THF (75 mL) was added t-butylnitrite (1.5 mL, 12.6 mmol) and the reaction was heated to reflux for 2 hours. The reaction was concentrated in vacuo and purified by flash chromatography (SiO₂, CH₂Cl₂) to give 52A (0.8 g 42percent). HPLC R_t=2.77 min.

Reference： [1] Patent: US2005/192310, 2005, A1, . Location in patent: Page/Page column 35

8
[ 1824-81-3 ]
[ 42753-71-9 ]
[ 91872-10-5 ]
[ 126325-46-0 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374
[2] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374

9
[ 91872-10-5 ]
[ 1000018-58-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 2, p. 273 - 276

[ 91872-10-5 ] Synthesis Path-Downstream 1~63

1
[ 1824-81-3 ]
[ 91872-10-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; dihydrogen peroxide; bromine; In tetrahydrofuran; at 65℃; for 8h;	(1) 10.81 g (0.1 mol) of 2-amino-6-methylpyridine was added to 200 ml of tetrahydrofuran, and 2 g of sulfuric acid was added and stirred. Add 100 ml of 35 wt% hydrogen peroxide, stir well, then add 15.98 g (0.1 mol) of bromine. The reaction was stirred at 65 C for 8 h to give the intermediate 2-amino-3,5-dibromo-6-methylpyridine;

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2987 - 2991
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5533 - 5539
[3]Journal of the American Chemical Society,1949,vol. 71,p. 1186,1191
[4]Patent: CN110128331,2019,A .Location in patent: Paragraph 0024-0032

2
[ 91872-10-5 ]
[ 500587-45-1 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 1186,1191

3
[ 1824-81-3 ]
[ 42753-71-9 ]
[ 91872-10-5 ]

Reference： [1]Heterocycles,1994,vol. 38,p. 529 - 540
[2]Russian Journal of Applied Chemistry,2005,vol. 78,p. 787 - 790

4
[ 1824-81-3 ]
[ 42753-71-9 ]
[ 91872-10-5 ]
[ 126325-46-0 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 369 - 374
[2]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 369 - 374

5
[ 91872-10-5 ]
[ 17157-48-1 ]
[ 217435-66-0 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 5108 - 5112

6
[ 5327-33-3 ]
[ 91872-10-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 173 - 178

7
[ 91872-10-5 ]
[ 89-95-2 ]
2-[[(3,5-dibromo-6-methylpyridin-2-yl)imino]methyl]-phenol [ No CAS ]

Reference： [1]Synthetic Communications,2002,vol. 32,p. 2395 - 2402

8
[ 91872-10-5 ]
[ 1000018-58-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

9
[ 91872-10-5 ]
[ 708-06-5 ]
1-[[(3,5-dibromo-6-methyl-2-pyridinyl)imino]methylenyl]-2-naphthalenol [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2004,vol. 689,p. 936 - 946

10
[ 91872-10-5 ]
[ 70-23-5 ]
[ 859787-43-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2790 - 2794

11
[ 91872-10-5 ]
[ 98-88-4 ]
[ 939053-47-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2987 - 2991

12
[ 91872-10-5 ]
[ 939053-14-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2987 - 2991

13
[ 91872-10-5 ]
C₁₃H₁₀N₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2987 - 2991

14
[ 91872-10-5 ]
C₁₄H₁₂N₂OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2987 - 2991

15
[ 91872-10-5 ]
C₁₉H₁₄N₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2987 - 2991

16
[ 91872-10-5 ]
C₁₉H₁₃FN₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2987 - 2991

17
[ 91872-10-5 ]
C₁₉H₁₃ClN₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2987 - 2991

18
[ 91872-10-5 ]
C₂₀H₁₃N₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2987 - 2991

19
[ 91872-10-5 ]
C₁₇H₁₂N₂S₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2987 - 2991

20
[ 91872-10-5 ]
[ 859788-25-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2790 - 2794

21
[ 91872-10-5 ]
[ 859787-98-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2790 - 2794

22
[ 91872-10-5 ]
[ 859787-64-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2790 - 2794

23
[ 91872-10-5 ]
6,8-dibromo-3-(2-ethoxy-phenyl)-5-methyl-2H-2,4,4b,9-tetraaza-fluoren-1-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2790 - 2794

24
[ 91872-10-5 ]
[ 859788-51-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2790 - 2794

25
[ 91872-10-5 ]
3,5-dibromo-2-bromomethyl-6-chloro-pyridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

26
[ 91872-10-5 ]
[ 547756-25-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

27
[ 91872-10-5 ]
1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-7-morpholin-4-yl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

28
[ 91872-10-5 ]
1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-7-(2,6-dimethyl-morpholin-4-yl)-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

29
[ 91872-10-5 ]
1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-7-piperidin-1-yl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

30
[ 91872-10-5 ]
7-(2-aza-bicyclo[2.2.1]hept-2-yl)-1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

31
[ 91872-10-5 ]
1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-7-(4-isopropyl-piperazin-1-yl)-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

32
[ 91872-10-5 ]
1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-7-(piperidin-4-ylamino)-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

33
[ 91872-10-5 ]
1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-7-(5-ethyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

34
[ 91872-10-5 ]
1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-7-(5-isopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

35
[ 91872-10-5 ]
7-(5-cyclopropyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

36
[ 91872-10-5 ]
1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-7-[4-(2-dimethylamino-ethyl)-piperazin-1-yl]-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

37
[ 91872-10-5 ]
4-[1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-7-yl]-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

38
[ 91872-10-5 ]
7-(5-cyclopropylmethyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

39
[ 91872-10-5 ]
5-[1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-7-yl]-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

40
[ 91872-10-5 ]
1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-7-[4-(2-pyrrolidin-1-yl-ethyl)-piperazin-1-yl]-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

41
[ 91872-10-5 ]
1-(2,6-dichloro-phenyl)-6-(2,4-difluoro-phenylsulfanyl)-7-[4-(2-pyrrolidin-1-yl-ethyl)-piperidin-1-yl]-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

42
[ 91872-10-5 ]
[ 217435-72-8 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 5108 - 5112

43
[ 91872-10-5 ]
3-benzylsulfanylmethyl-6,8-dibromo-5-methyl-imidazo[1,2-a]pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 5108 - 5112

44
[ 91872-10-5 ]
[ 632628-07-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	With tetrafluoroboric acid; sodium nitrite; at 0 - 60℃; for 9h;	5-Bromo-2-amino-6-methylpyridine (10 kg) was dissolved in HBF4 (200 L, 48%). After the reaction was cooled to 0 C, NaNO 2 (6.8 kg) was added portionwise.After the addition was completed, the reaction was allowed to rise to room temperature. After reacting for 6 hours, the reaction was continued to 3 hours by heating to 60 C.After returning to room temperature, water (200 L) was added, followed by extraction with dichloromethane (100 L×5).The extracts were combined and dried over sodium sulfate. After concentration by filtration, the reaction product was obtained as 5-bromo-2-fluoro-6-methylpyridine (78% yield: 77%).
	With pyridine hydrogenfluoride; sodium nitrite; at -10℃;	To a stirred solution of <strong>[91872-10-5]2-amino-3, [5-DIBROMO-6-METHYLPYRIDINE]</strong> (25. 0g 0. 094moles) in [HF. PYRIDINE (50ML)] was added NaN02 (9.73g, 0. [141MOLES)] slowly [AT-10C.] Reaction was stirred until complete by TLC. Reaction mixture was diluted with [150ML] of dichloromethane. The resulting organic phase was back extracted three times with 100mL of water. The organic phase was dried over sodium sulphate and concentrated. Resulting oil was subjected to flash chromatography (gradient: 0 - 20% ether in hexanes) and resulted in the fluorinated compound 2. 1H NMR ( CDCI, 500 MHz, ppm) 8.05 [(1H,] d, 4 Hz); 2.6 (3H, s)

Reference： [1]Patent: CN108341769,2018,A .Location in patent: Paragraph 0021; 0023; 0033; 0034
[2]Patent: WO2003/103590,2003,A2 .Location in patent: Page 26-27

45
[ 91872-10-5 ]
[ 38749-87-0 ]

Yield	Reaction Conditions	Operation in experiment
42%	With tert.-butylnitrite; In tetrahydrofuran; for 2h;Heating / reflux;	To a solution of 3,5-dibromo-6-methyl-pyridin-2-ylamine (2.0 g, 7.5 mmol) in THF (75 mL) was added t-butylnitrite (1.5 mL, 12.6 mmol) and the reaction was heated to reflux for 2 hours. The reaction was concentrated in vacuo and purified by flash chromatography (SiO2, CH2Cl2) to give 52A (0.8 g 42%). HPLC Rt=2.77 min.

Reference： [1]Patent: US2005/192310,2005,A1 .Location in patent: Page/Page column 35

46
[ 91872-10-5 ]
[ 140-89-6 ]
5-hydroxymethyl-2-thioxo-2,3-dihydrothiazolo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In 1-methyl-pyrrolidin-2-one;	PREPARATIVE EXAMPLE 21 5-HYDROXYMETHYL-2-THIOXO-2,3-DIHYDROTHIAZOLO[4,5-B]PYRIDINE STR146 Step 1: 5-methyl-6-bromo-2-thioxo-2,3-dihydrothiazolo[4,5-b]pyridine Potassium ethyl xanthate (4.8 g, 30 mmol) and 2-amino-3,5-dibromo-6-picoline (2.66 g, 10 mmol) were dissolved in N-methylpyrrolidinone (10 mL) and the solution was placed in a 170 C. oil bath for 4.5 hours under nitrogen. The dark solution was cooled to room temperature, diluted with water (50 ml) and acidified with acetic acid (5 mL). The suspension was filtered and the collected solid was washed with water (20 mL) and dried under vacuum to give the title compound as a light yellow solid (2.16 g, 83%). 1 H NMR (DMSO-d6, 500 MHz) delta2.50 (s, Me) and 8.22 (s, ArH). 13 C NMR (DMSO-d6, 500 MHz) delta191.2, 154.2, 152.6, 130.7, 123.1, 9.3, and 24.5 ppm.

Reference： [1]Patent: US5496816,1996,A

47
[ 91872-10-5 ]
[ 2032-35-1 ]
[ 217435-66-0 ]

Yield	Reaction Conditions	Operation in experiment
		1 A mixture of 2-bromo-l , l -diethoxyethane (1 .78 g, 9.03 mmol) and 48% hydrobromic acid (2 mL) was stirred at reflux for 2 h. The reaction was then cooled to room temperature and treated with sodium bicarbonate until gas evolution ceased. The mixture was filtered and the filter cake washed with ethanol (10 mL). 3,5-Dibromo-6-methylpyridin-2-amine (1 .50 g, 5.62 mmol) was then added to the filtrate and the mixture stirred at reflux for 5.5 h. The reaction was then cooled to room temperature and concentrated under reduced pressure. The residue was diluted with 0.19 M aqueous potassium carbonate (75 m L) and stirred at room temperature for 1 h. After this time, the resulting suspension was filtered and the filter cake purified by chromatography (silica, gradient, hexanes to ethyl acetate) to afford 6,8- dibromo-5-methylimidazo[ l ,2-a]pyridine as a light orange solid: NMR (400 MHz,DMSO- )d 8.1 1 (d, J = 1.2 Hz, 1H), 7.84 (s, 1 H), 7.72 (d, J = 1 .2 Hz, 1 H), 2.71 (s, 3H); ESI MS m/z 289.1 [M + H]+.
		Example 6 Preparation of 6,8-dibromo-5-methylimidazo[1,2-a]pyridine A mixture of 2-bromo-1,1-diethoxyethane (1.78 g, 9.03 mmol) and 48% hydrobromic acid (2 mL) was stirred at reflux for 2 h. The reaction was then cooled to room temperature and treated with sodium bicarbonate until gas evolution ceased. The mixture was filtered and the filter cake washed with ethanol (10 mL). 3,5-Dibromo-6-methylpyridin-2-amine (1.50 g, 5.62 mmol) was then added to the filtrate and the mixture stirred at reflux for 5.5 h. The reaction was then cooled to room temperature and concentrated under reduced pressure. The residue was diluted with 0.19 M aqueous potassium carbonate (75 mL) and stirred at room temperature for 1 h. After this time, the resulting suspension was filtered and the filter cake purified by chromatography (silica, gradient, hexanes to ethyl acetate) to afford 6,8-dibromo-5-methylimidazo[1,2-a]pyridine as a light orange solid: 1H NMR (400 MHz, DMSO-d6.) d 8.11 (d, J=1.2 Hz, 1H), 7.84 (s, 1H), 7.72 (d, J=1.2 Hz, 1H), 2.71 (s, 3H); ESI MS m/z 289.1 [M+H]+.

Reference： [1]Patent: WO2011/112995,2011,A1 .Location in patent: Page/Page column 53; 54
[2]Patent: US2014/148430,2014,A1 .Location in patent: Paragraph 0336

48
[ 91872-10-5 ]
[ 1229210-78-9 ]

Reference： [1]Patent: WO2011/112995,2011,A1
[2]Patent: US2014/148430,2014,A1

49
[ 91872-10-5 ]
[ 1333509-10-6 ]

Reference： [1]Patent: WO2011/112995,2011,A1
[2]Patent: US2014/148430,2014,A1

50
2-(bromomethyl)-5-methyl-1H-imidazo[1,2-a]pyridinium bromide [ No CAS ]
[ 91872-10-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2012,vol. 47,p. 1280 - 1285

51
2-(bromomethyl)-2-hydroxy-5-methyl-1H,2H,3H-imidazo[1,2-a]pyridinium bromide [ No CAS ]
[ 91872-10-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2012,vol. 47,p. 1280 - 1285

52
[ 91872-10-5 ]
[ 3886-69-9 ]
[ 1021918-52-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5533 - 5539

53
[ 91872-10-5 ]
[ 98-86-2 ]
[ 1629889-72-0 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 27301 - 27307

54
[ 91872-10-5 ]
C₁₄H₁₃Br₂ClN₂O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

55
[ 91872-10-5 ]
C₂₁H₁₅BrCl₃N₃O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

56
[ 91872-10-5 ]
C₂₁H₁₆Br₂Cl₃N₃O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

57
[ 91872-10-5 ]
[ 632628-12-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 273 - 276

58
[ 1121-60-4 ]
[ 91872-10-5 ]
ammonium hexafluorophosphate [ No CAS ]
[ 52462-29-0 ]
[(η6-p-cymene)RuCl(κ2-N,N-(3,5-dibromo-6-methylpyridin-2-yl)pyridin-2-ylmethyleneamine)]·PF₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		Ruthenium (II) p-cymene Dimer (3) (10mg, 0.016 mmol) was dissolved in 5 ml ofmethanol in 25 mL RB flask placed on a magnetic stirrer and stirred for 30 min.Subsequently, Pyridine-2-carboxaldehyde (1)& <strong>[91872-10-5]2-amino-3,5-dibromo-6-methylpyridine</strong> (2j) (2:2 equivalent with respect to theruthenium dimer) was added to reaction mixture and then stirred continuouslyfor 24 h at room temperature.Ammonium hexafluorophosphate (1:1) was added, colorchange was observed from deep yellow to deep red. Then we performed the TLC in1% methanol in ethyl acetate. After completion of the reaction we haveevaporated the methanol by using rotator evaporator. The crude product was recrystallizedfrom 5% methanol in diethyl ether; fine brown crystal was obtained with 96%yield. Spectral Data Yield: 96 %, Mp: 148-150C, Rf (1% MeOH in EthylAcetate):0.32IR (cm-1): 519, 553, 634, 692,739, 777, 827, 878, 1059, 1234, 1304, 1333, 1375, 1408 (aromatic C=C stretch),1441 (aromatic C=C stretch), 1585 (-C=N stretch), 2365, 2926, 2963 (aromaticC-H stretch), 3123 (aromatic C-H stretch), 3603, 3634.1H NMR (CDCl3, 400MHz): delta 1.05(d, 3H, J = 6.8 Hz, Cymene CH3),1.12(d, 3H, J = 6.8 Hz, Cymene CH3),2.20 (s, 3H, Cymene CH3), 2.75 (s, 3H, CH3),2.78-2.83 (m, 1H, Cymene CH), 5.45 (d, 1H, J = 5.6 Hz, Cymene ArH), 5.73 (d, 1H, J = 6.4 Hz, Cymene ArH), 5.81 (d, 1H, J = 6 Hz, Cymene ArH), 5.89 (d, 1H, J = 6 Hz, Cymene ArH), 7.85(d, 1H, J = 5.2 Hz, ArH), 8.12 (d,1H, J = 6.4, ArH), 8.18 (d, 1H, J = 7.2,ArH), 8.26 (s, 1H, ArH), 8.61(s, 1H, ArH), 9.47 (brs, 1H, imine CH); 13C NMR (CDCl3, 400 MHz): delta17.8 (CH3),20.6 (CH3), 21.3 (CH3), 23.3 (CH3), 30.1 (CH),83.0, 85.1, 85.7, 102.7, 106.5, 108.1, 120.7, 129.9, 138.7, 145.3, 152.1,155.5, 155.6, 155.8, 170.3(-C=N); 31P NMR (CDCl3, 400 MHz): delta -153.05 (m, PF6);19F NMR (DMSO-d6, 400 MHz): delta -73.03(6F, PF6);ESI-MS (MeOH): m/z: 626 [M]+; HRMS (ESI): m/z calcd for C22H23N3Br2ClRu+:625.8970 [M]+; found: 625.8974 [M]+

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2695 - 2700

59
[ 17084-13-8 ]
[ 1121-60-4 ]
[ 91872-10-5 ]
[ 52462-29-0 ]
[(η6-p-cymene)RuCl(κ2-N,N-(3,5-dibromo-6-methylpyridin-2-yl)pyridin-2-ylmethyleneamine)]·PF₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4154 - 4155

60
[ 91872-10-5 ]
[ 532-55-8 ]
N-[(3,5-dibromo-6-methylpyridin-2-yl)carbamothioyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6.67 g	In acetone; for 8h;Reflux;	Reference Example 245 N-[(3,5-dibromo-6-methylpyridin-2-yl)carbamothioyl]benzamide An acetone solution (14.0 mL) of <strong>[91872-10-5]2-amino-3,5-dibromo-6-methylpyridine</strong> (5.05 g) and benzoyl isothiocyanate (3.25 g) was heated under reflux for 8 h After cooling to room temperature, diisopropy ether was added, and the resulting solid was collected by filtration and dried to give the title compound (6.67 g). MS(ESI)m/z; 428,430,432[M+H]+

Reference： [1]Patent: EP3372601,2018,A1 .Location in patent: Paragraph 0628; 0629

61
[ 91872-10-5 ]
methyl (3,5-dibromo-6-methylpyridin-2-yl)carbamate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 3157 - 3163

62
[ 91872-10-5 ]
C₆H₆Br₂N₂O [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 3157 - 3163

63
[ 91872-10-5 ]
[ 126325-46-0 ]

Yield	Reaction Conditions	Operation in experiment
77.2%	With methyllithium; In tetrahydrofuran; at 0℃; for 1h;	(2) <strong>[91872-10-5]2-amino-3,5-dibromo-6-methylpyridine</strong> was added to 200 ml of anhydrous tetrahydrofuran, and after stirring, the temperature was lowered to 0 C. 6.4 g (0.1 mol) of methyllithium was added, and after 1 h of reaction, 2-amino-3-bromo-6-methylpyridine was obtained. The overall yield of the two-step reaction was 77.2%.Show moreShow less

Reference： [1]Patent: CN110128331,2019,A .Location in patent: Paragraph 0024-0032

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[ 91872-10-5 ] Synthesis Path-Upstream 1~9

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Bromides

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Pyridines

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