[ CAS No. 89466-17-1 ] {[proInfo.proName]}

Name: 89466-17-1|6-Bromo-5-methylpyridin-2-amine|95%
Brand: Ambeed
SKU: A491418
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Quality Control of [ 89466-17-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 89466-17-1 ]

Product Details of [ 89466-17-1 ]

CAS No. :	89466-17-1	MDL No. :	MFCD20704687
Formula :	C₆H₇BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DDCMBKXJOGOCPM-UHFFFAOYSA-N
M.W :	187.04	Pubchem ID :	59166153
Synonyms :

Calculated chemistry of [ 89466-17-1 ]

Physicochemical Properties

Num. heavy atoms :	9
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 :	41.31
TPSA :	38.91 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.62
Log Po/w (XLOGP3) :	1.89
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	1.33
Log Po/w (SILICOS-IT) :	1.78
Consensus Log Po/w :	1.67

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.68
Solubility :	0.387 mg/ml ; 0.00207 mol/l
Class :	Soluble
Log S (Ali) :	-2.33
Solubility :	0.876 mg/ml ; 0.00468 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.91
Solubility :	0.232 mg/ml ; 0.00124 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.88

Safety of [ 89466-17-1 ]

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 [ 89466-17-1 ]

* 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 [ 89466-17-1 ]
Downstream synthetic route of [ 89466-17-1 ]

[ 89466-17-1 ] Synthesis Path-Upstream 1~7

1
[ 19230-57-0 ]
[ 89466-17-1 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: With pyridine; trifluoromethylsulfonic anhydride In acetonitrile at 71℃; for 1.5 h; Stage #2: With ethanolamine In acetonitrile at 10 - 20℃; for 13 h;	To a stirred solution of 2-bromo-3-methylpyridine-1-oxide (18g) and pyridine (3OmL) in acetonitrile (l8OmL) at about 71°C, was added a solution of methanesulfonic anhydride (33.31g) in acetonitrile (4OmL). The reaction mixture was stirred for about 90mm at about the same temperature and acetonitrile (3 OmL) was added to it. The reaction mixturewas cooled to about 10°C to about 15°C and ethanolamine (58.59g) was added to it. The reaction mixture was stirred for about 1 3h at about room temperature and water and ethyl acetate were added to it. The two layers were separated and the organic layer was washed with water and saturated brine solution, dried and concentrated under reduced pressure at about 45°C. The residue was purified by column chromatography (25-30 percent ethyl acetate in hexane). Yield: big (56percent)‘H NIVIR (300IVIHz, CDC13): ö 7.24-7.22 (d,J8.1 Hz,1H), 6.39-6.36 (d,J=8.4 Hz,1H),4.27 (brs,2H), 2.21 (s,3H)IR: 3365, 3200, 2915, 1636, 1601, 1475, 1374, 1058, 820 cmMass [M+Hfb: 187.05

Reference： [1] Patent: WO2017/56031, 2017, A1, . Location in patent: Paragraph 0167; 0168; 0175

2
[ 442129-37-5 ]
[ 89466-17-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	at 140℃; for 6 h;	3.4 g of chloride IA was added to 10 ml of phosphorus tribromide and heated to 140 degrees.After 6 hours of reaction, the TLC reaction was complete, dropped to ambient temperature, and slowly added to crushed ice.Add 40percent sodium hydroxide to adjust the pH to 10, a large amount of solids are precipitated, filtered, and the filter cake is washed with 20 ml of water.The product IB 4g was obtained in a yield of 91percent.

Reference： [1] Patent: CN108658851, 2018, A, . Location in patent: Paragraph 0071; 0072; 0073

3
[ 19230-57-0 ]
[ 89466-17-1 ]

Yield	Reaction Conditions	Operation in experiment
16%	Stage #1: With pyridine; trifluoromethylsulfonic anhydride In acetonitrile at 80℃; for 1 h; Stage #2: With ethanolamine In acetonitrile at 10 - 20℃; for 3 h;	To a stirred solution of 2-bromo-3-methyl pyridine-1-oxide (25g) and pyridine (42g) in acetonitrile (250mL) at about 70°C, was added a solution of trifluoromethanesulfonic anhydride (55g) in acetonitrile (5OmL). The reaction mixture was stirred for about lh atabout the same temperature. The mixture was cooled to about 10°C to about 15°C and ethanolamine (80.52g) was added to it. The reaction mixture was stirred for about 3h at about room temperature and water and ethyl acetate were added to it. The two layers were separated and the organic layer was washed with saturated brine solution, dried and concentrated under reduced pressure at about 40°C. The residue was purified by columnchromatography (15-20percent ethyl acetate in hexane). Yield: 4g (16percent)‘H NIVIR (300IVIHz, CDC13): ö 7.26-7.24 (d,J8.lOHz,1H), 6.42-6.39 (d,J8.4Hz,1H), 4.28 (brs,2H), 2.22 (s,3H)‘3CNMR(400MHz, CDC13): 156.52, 141.56, 140.50, 122.99, 107.26, 20.58 IR: 3364, 3199, 2913, 1635, 1601, 1373, 1058, 819 cm4—Amino-2-bromo-3-methyl pyridine (3g) was obtained which was eluted at 25-30percent ethyl acetate in hexane.‘H NIVIR (300IVIHz, CDC13): ö 7.82-7.80 (d,J5.4Hz,1H), 6.48-6.46 (d,J 5.4Hz,1H), 4.35 (brs,2H), 2.21 (s,3H)‘3CNMR(400MHz, CDC13): 152.70, 146.94, 145.05, 116.88, 109.25, 15.73
0.34 g	Stage #1: With methanesulfonic anhydride In pyridine; acetonitrile at 70℃; for 1.33 h; Stage #2: With ethanolamine In pyridine; acetonitrile at 30℃; for 15.17 h; Inert atmosphere	A mixture of 6-bromo 5-methyl pyridine N-oxide (1 .2 g) and Pyridine (2.06 mL) in acetonitrile (4.8 mL) was heated to 70°C and a solution of methane sulfonic anhydride (1 .667 g in 2.4 mL of acetonitrile) was added to it drop wise over a period of 20 minutes. The reaction mixture was stirred for 1 hour at 70°C and allowed to cool to 30°C. Ethanol amine (3.851 mL) was added drop wise over 10 minutes under nitrogen atmosphere at 30°C and stirred the reaction mixture for 15 hours at the same temperature. The reaction mixture was quenched with water (15 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic solution was dried over sodium sulfate and concentrated under reduced pressure to obtain crude product. The crude product was purified by column chromatography using 60-120 mesh and 20-30percent ethyl acetate / hexane as eluent to obtain 0.32 g of 6-bromo 5-methyl pyridin-2-amine with 93.41 percent purity by HPLC as a brown solid and 0.34 g of 2-bromo 3-methyl pyridin-4-amine with 97.94percent purity by HPLC as a brown solid.

Reference： [1] Patent: WO2017/56031, 2017, A1, . Location in patent: Paragraph 0165; 0166
[2] Patent: WO2017/175161, 2017, A1, . Location in patent: Page/Page column 51-52

4
[ 19230-57-0 ]
[ 442129-37-5 ]
[ 89466-17-1 ]

Reference： [1] Tetrahedron, 2011, vol. 67, # 47, p. 9063 - 9066

5
[ 3430-17-9 ]
[ 89466-17-1 ]

Reference： [1] Patent: WO2017/56031, 2017, A1,
[2] Patent: WO2017/56031, 2017, A1,

6
[ 936727-56-9 ]
[ 89466-17-1 ]

Reference： [1] Patent: CN108658851, 2018, A,

7
[ 3430-17-9 ]
[ 89466-17-1 ]

Reference： [1] Patent: WO2017/175161, 2017, A1,

[ 89466-17-1 ] Synthesis Path-Downstream 1~29

3
[ 19230-57-0 ]
[ 442129-37-5 ]
[ 89466-17-1 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 20a and 20b (5.4 g, ?17 mmol) in concentrated HCl (35 mL) was refluxed for 45 h whereupon it was concentrated under reduced pressure. The residue was adjusted to pH 8 by the addition of satd aqueous NaHCO3 and extracted with CH2Cl2 (3×80 mL). The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated under reduced pressure to give a mixture (1:1) of 24a and 25b (2.5 g, ?15 mmol, 92%) as a white solid. A sample was separated by HPLC and the individual heterocycles were characterized as follows: for 24a: mp 96-98 C; IR (KBr): 3364, 3200, 1600, 1475, 1373, 819 cm-1; 1H NMR (400 MHz, CDCl3): delta=7.25 (d, J=8.0 Hz, 1H), 6.38 (d, J=8.0 Hz, 1H), 4.48 (br s, 2H), 2.24 (s, 3H); 13C NMR (100 MHz, CDCl3): delta=156.4, 141.7, 140.5, 123.3, 107.3, 20.7; HRMS-ESI: calcd for C6H8BrN2 (M+H)+: 186.9871 and 188.9850; found: 186.9865 and 188.9845. For 24b: mp 90-92 C; IR (KBr): 3362, 1639, 1479, 1378, 820 cm-1; 1H NMR (400 MHz, CDCl3): delta=7.29 (d, J=8.0 Hz, 1H), 6.36 (d, J=8.0 Hz, 1H), 4.41 (br s, 2H), 2.23 (s, 3H); 13C NMR (100 MHz, CDCl3): delta=156.4, 148.8, 141.2, 120.7, 106.9, 18.3; HRMS-ESI: calcd for C6H8ClN2 (M+H)+: 143.0376; found:143.0371.

Reference： [1]Tetrahedron,2011,vol. 67,p. 9063 - 9066

4
(2S,4S)-1-(tert-butoxycarbonyl)-4-((dimethylamino)methyl)-4-fluoropyrrolidine-2-carboxylic acid [ No CAS ]
[ 89466-17-1 ]
C₁₉H₂₈BrFN₄O₃ [ No CAS ]

Reference： [1]Patent: WO2017/35353,2017,A1 .Location in patent: Page/Page column 592

5
[ 89466-17-1 ]
(2S,4S)-1-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-N-(6-bromo-3-methylpyridin-2-yl)-4-((dimethylamino)methyl)-4-fluoropyrrolidine-2-carboxamide [ No CAS ]

Reference： [1]Patent: WO2017/35353,2017,A1

6
[ 89466-17-1 ]
(x)C₂HF₃O₂*C₁₉H₂₈BrFN₄O₃ [ No CAS ]

Reference： [1]Patent: WO2017/35353,2017,A1

7
[ 89466-17-1 ]
[ 203866-14-2 ]
tert-butyl (2S,4R)-2-((6-bromo-5-methylpyridin-2-yl)carbamoyl)-4-fluoropyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%		To a stirred solution of (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (250 mg, 1.07 mmole) in 10 mL of CH2Cl2, was added 1-methyl imidazole (0.21 mL, 2.5 equiv.) at 0-5 C. under nitrogen atmosphere. The reaction mixture was stirred for 10 min at 0-5 C. and then added methane sulfonyl chloride (0.1 mL, 1.2 equiv) at the same temperature. It was stirred for 1 h at 0-5 C. Then <strong>[89466-17-1]6-bromo-5-methylpyridin-2-amine</strong> (200 mg, 1 equiv) was added, and stirred for 18h at room temperature. Water (10 mL) was added to the reaction mixture, layers were separated and aqueous layer was extracted with DCM (3×10 mL). The combined organic layer was washed with 1N HCl (10 mL), followed by Sat NaHCO3 (10 mL) and then with brine (10 mL). Combined organic layer was dried over Na2SO4, concentrated and to obtain titled compound 404 mg (quantitative yield).

Reference： [1]Patent: WO2017/35353,2017,A1 .Location in patent: Paragraph 1457

8
[ 19230-57-0 ]
[ 89466-17-1 ]
4-amino-2-bromo-3-methylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%; 3 g		To a stirred solution of 2-bromo-3-methyl pyridine-1-oxide (25g) and pyridine (42g) in acetonitrile (250mL) at about 70C, was added a solution of trifluoromethanesulfonic anhydride (55g) in acetonitrile (5OmL). The reaction mixture was stirred for about lh atabout the same temperature. The mixture was cooled to about 10C to about 15C and ethanolamine (80.52g) was added to it. The reaction mixture was stirred for about 3h at about room temperature and water and ethyl acetate were added to it. The two layers were separated and the organic layer was washed with saturated brine solution, dried and concentrated under reduced pressure at about 40C. The residue was purified by columnchromatography (15-20% ethyl acetate in hexane). Yield: 4g (16%)?H NIVIR (300IVIHz, CDC13): oe 7.26-7.24 (d,J8.lOHz,1H), 6.42-6.39 (d,J8.4Hz,1H), 4.28 (brs,2H), 2.22 (s,3H)?3CNMR(400MHz, CDC13): 156.52, 141.56, 140.50, 122.99, 107.26, 20.58 IR: 3364, 3199, 2913, 1635, 1601, 1373, 1058, 819 cm4-Amino-2-bromo-3-methyl pyridine (3g) was obtained which was eluted at 25-30% ethyl acetate in hexane.?H NIVIR (300IVIHz, CDC13): oe 7.82-7.80 (d,J5.4Hz,1H), 6.48-6.46 (d,J 5.4Hz,1H), 4.35 (brs,2H), 2.21 (s,3H)?3CNMR(400MHz, CDC13): 152.70, 146.94, 145.05, 116.88, 109.25, 15.73
0.34 g		A mixture of 6-bromo 5-methyl pyridine N-oxide (1 .2 g) and Pyridine (2.06 mL) in acetonitrile (4.8 mL) was heated to 70C and a solution of methane sulfonic anhydride (1 .667 g in 2.4 mL of acetonitrile) was added to it drop wise over a period of 20 minutes. The reaction mixture was stirred for 1 hour at 70C and allowed to cool to 30C. Ethanol amine (3.851 mL) was added drop wise over 10 minutes under nitrogen atmosphere at 30C and stirred the reaction mixture for 15 hours at the same temperature. The reaction mixture was quenched with water (15 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic solution was dried over sodium sulfate and concentrated under reduced pressure to obtain crude product. The crude product was purified by column chromatography using 60-120 mesh and 20-30% ethyl acetate / hexane as eluent to obtain 0.32 g of 6-bromo 5-methyl pyridin-2-amine with 93.41 % purity by HPLC as a brown solid and 0.34 g of 2-bromo 3-methyl pyridin-4-amine with 97.94% purity by HPLC as a brown solid.

Reference： [1]Patent: WO2017/56031,2017,A1 .Location in patent: Paragraph 0165; 0166
[2]Patent: WO2017/175161,2017,A1 .Location in patent: Page/Page column 51-52

9
[ 19230-57-0 ]
[ 89466-17-1 ]

Yield	Reaction Conditions	Operation in experiment
56%		To a stirred solution of <strong>[19230-57-0]2-bromo-3-methylpyridine-1-oxide</strong> (18g) and pyridine (3OmL) in acetonitrile (l8OmL) at about 71C, was added a solution of methanesulfonic anhydride (33.31g) in acetonitrile (4OmL). The reaction mixture was stirred for about 90mm at about the same temperature and acetonitrile (3 OmL) was added to it. The reaction mixturewas cooled to about 10C to about 15C and ethanolamine (58.59g) was added to it. The reaction mixture was stirred for about 1 3h at about room temperature and water and ethyl acetate were added to it. The two layers were separated and the organic layer was washed with water and saturated brine solution, dried and concentrated under reduced pressure at about 45C. The residue was purified by column chromatography (25-30 % ethyl acetate in hexane). Yield: big (56%)?H NIVIR (300IVIHz, CDC13): oe 7.24-7.22 (d,J8.1 Hz,1H), 6.39-6.36 (d,J=8.4 Hz,1H),4.27 (brs,2H), 2.21 (s,3H)IR: 3365, 3200, 2915, 1636, 1601, 1475, 1374, 1058, 820 cmMass [M+Hfb: 187.05

Reference： [1]Patent: WO2017/56031,2017,A1 .Location in patent: Paragraph 0167; 0168; 0175

10
[ 3430-17-9 ]
[ 89466-17-1 ]

Reference： [1]Patent: WO2017/56031,2017,A1
[2]Patent: WO2017/56031,2017,A1

11
[ 89466-17-1 ]
[ 1160221-26-0 ]

Reference： [1]Patent: WO2017/56031,2017,A1
[2]Patent: WO2017/56031,2017,A1

12
[ 89466-17-1 ]
Lumacaftor [ No CAS ]

Reference： [1]Patent: WO2017/56031,2017,A1
[2]Patent: WO2017/56031,2017,A1

13
[ 1004294-65-8 ]
[ 89466-17-1 ]
N-(6-bromo-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With pyridine; In dichloromethane; at 20℃; for 3h;	To a solution of <strong>[89466-17-1]6-amino-2-bromo-3-methylpyridine</strong> (7.72g) and pyridine (9.7g) in dichloromethane (SOOmL) was added a solution of 1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl chloride in dichloromethane (2OmL). The reaction mixture was stirred at about room temperature for about 3h and water was added to it. The two layers were separated and the organic layer was treated with hydrochloric acid solution and then with sodium bicarbonate solution. The organic layer was washed with water, saturated brine solution, then treated with charcoal, filtered through hyflo bed, concentrated underreduced pressure at about 35C to about 45C and was co-distilled with hexane. A mixture of the obtained residue in hexane was stirred for about 5h. The solid obtained was filtered and dried at about 60C for about 8h. Yield: 12.4g (73%).
0.15 g	With triethylamine; In dichloromethane; at 0 - 30℃; for 18.083h;Inert atmosphere;	6-bromo 5-methyl pyridin-2-amine (0.1 g) was dissolved in dichloromethane (1 mL) under nitrogen atmosphere. The solution was cooled to 0C and triethyl amine (0.149 mL) was added. 1 -(2,2-difluorobenzo[d][1 ,3]dioxol-5- yl)cyclopropane-1 -carbonyl chloride (0.209 g) in dichloromethane (0.5 mL) was added drop wise into the reaction mixture in 5 minutes. The reaction mixture was warmed to 30C and stirred for 18 hours at the same temperature. Quenched the reaction mixture with saturated potassium hydroxide solution (30 mL) and extracted with dichloromethane (30 mL). The organic solution was dried over sodium sulphate and evaporated under reduced pressure to afford crude product. The crude product was purified by column chromatography using 60-120 mesh and 10-20% ethyl acetate / hexane as eluent to obtain the title compound as brown color solid. Yield: 0.150 g; Purity by HPLC: 96.90%

Reference： [1]Patent: WO2017/56031,2017,A1 .Location in patent: Paragraph 0170; 0178
[2]Patent: WO2017/175161,2017,A1 .Location in patent: Page/Page column 52-53

14
[ 862574-88-7 ]
[ 89466-17-1 ]
N-(6-bromo-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		To a solution of 1 -(2,2-difluoro-l,3-benzodioxol-5-yl)cyclopropanecarboxylic acid (5g) in toluene (5OmL) and dimethylformamide (1 .25mL) was slowly added thionyl chloride(3.63mL) and the reaction mixture was stirred for about 3h at about 80C. The reaction mixture was concentrated under reduced pressure at about 50C. To the obtained residue in dichloromethane (lOmL) were added <strong>[89466-17-1]6-amino-2-bromo-3-methylpyridine</strong> (3.86g) in dichloromethane (SOmL) and pyridine (SmL) at about room temperature. The reaction mixture was maintained for about 3h at about room temperature and water was added toit. The two layers were separated and the organic layer was treated with 10% hydrochloric acid solution and then with sodium bicarbonate solution. The organic layer was washed with water and brine solution, treated with charcoal, filtered, concentrated under reduced pressure at about 50C and was co-distilled with hexane. Hexane was added to the obtained residue and the mixture was stirred for about 6h. The solid obtainedwas filtered and dried at about 60C for about 8h. Yield: 65.3g (76%)

Reference： [1]Patent: WO2017/56031,2017,A1 .Location in patent: Paragraph 0171; 0179; 0180; 0181

15
[ 3430-17-9 ]
[ 89466-17-1 ]
4-amino-2-bromo-3-methylpyridine [ No CAS ]

Reference： [1]Patent: WO2017/175161,2017,A1

16
[ 931-53-3 ]
[ 89466-17-1 ]
[ 121-33-5 ]
4-(6-bromo-3-(cyclohexylamino)-5-methylimidazo[1,2-a]pyridin-2-yl)-2-methoxyphenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With ammonium chloride; at 75℃; for 2h;Autoclave;	General procedure: To a solution of 0.052 g ammonium chloride (1 mmol) in 4 mL water or methanol was added isocyanide (1.2 mmol), aromatic aldehyde (1.1 mmol), and 2-aminopyridine (1 mmol) and sealed in stainless steel autoclave with a Teflon-coated, and then the autoclave was put in the oven at 75oC in 2 h. The autoclave was taken out and cooled to room temperature. The reaction mixture was put into 30 mL cooled water to afford the product as a precipitate. The solid residue was filtered and crystallized from ethyl acetate to give products.

Reference： [1]Arkivoc,2018,vol. 2018,p. 184 - 193

17
[ 89466-17-1 ]
[ 68498-54-4 ]
[ 134-96-3 ]
4-(6-bromo-3-(cyclopentylamino)-5-methylimidazo[1,2-a]pyridin-2-yl)-2,6-dimethoxyphenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With ammonium chloride; at 75℃; for 2h;Autoclave;	General procedure: To a solution of 0.052 g ammonium chloride (1 mmol) in 4 mL water or methanol was added isocyanide (1.2 mmol), aromatic aldehyde (1.1 mmol), and 2-aminopyridine (1 mmol) and sealed in stainless steel autoclave with a Teflon-coated, and then the autoclave was put in the oven at 75oC in 2 h. The autoclave was taken out and cooled to room temperature. The reaction mixture was put into 30 mL cooled water to afford the product as a precipitate. The solid residue was filtered and crystallized from ethyl acetate to give products.

Reference： [1]Arkivoc,2018,vol. 2018,p. 184 - 193

18
[ 442129-37-5 ]
[ 89466-17-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With phosphorus tribromide; at 140℃; for 6h;	3.4 g of chloride IA was added to 10 ml of phosphorus tribromide and heated to 140 degrees.After 6 hours of reaction, the TLC reaction was complete, dropped to ambient temperature, and slowly added to crushed ice.Add 40% sodium hydroxide to adjust the pH to 10, a large amount of solids are precipitated, filtered, and the filter cake is washed with 20 ml of water.The product IB 4g was obtained in a yield of 91%.

Reference： [1]Patent: CN108658851,2018,A .Location in patent: Paragraph 0071; 0072; 0073

19
5-bromo-6-chloropyridin-2-ylamine [ No CAS ]
[ 89466-17-1 ]

Reference： [1]Patent: CN108658851,2018,A
[2]Patent: CN108658851,2018,A
[3]Patent: CN108658851,2018,A

20
C₁₀H₁₂BrClN₂O [ No CAS ]
[ 89466-17-1 ]