[ CAS No. 50998-17-9 ] {[proInfo.proName]}

Name: 50998-17-9|6-Bromoquinoxaline|98%
Brand: Ambeed
SKU: A451473
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Quality Control of [ 50998-17-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 50998-17-9 ]

Product Details of [ 50998-17-9 ]

CAS No. :	50998-17-9	MDL No. :	MFCD00837757
Formula :	C₈H₅BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NOYFLUFQGFNMRB-UHFFFAOYSA-N
M.W :	209.04	Pubchem ID :	610939
Synonyms :

Calculated chemistry of [ 50998-17-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.24
TPSA :	25.78 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) :	-5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	2.27
Log Po/w (WLOGP) :	2.39
Log Po/w (MLOGP) :	1.61
Log Po/w (SILICOS-IT) :	2.65
Consensus Log Po/w :	2.16

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.24
Solubility :	0.121 mg/ml ; 0.000577 mol/l
Class :	Soluble
Log S (Ali) :	-2.45
Solubility :	0.745 mg/ml ; 0.00356 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.19
Solubility :	0.0136 mg/ml ; 0.0000652 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.63

Safety of [ 50998-17-9 ]

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

Application In Synthesis of [ 50998-17-9 ]

* 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 [ 50998-17-9 ]
Downstream synthetic route of [ 50998-17-9 ]

[ 50998-17-9 ] Synthesis Path-Upstream 1~10

1
[ 50998-17-9 ]
[ 6298-37-9 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 11, p. 2809 - 2812
[2] Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737

2
[ 50998-17-9 ]
[ 7467-91-6 ]

Reference： [1] Journal of Organic Chemistry, 2014, vol. 79, # 11, p. 5351 - 5358
[2] Journal of the American Chemical Society, 2016, vol. 138, # 41, p. 13493 - 13496
[3] Organic Letters, 2017, vol. 19, # 11, p. 3033 - 3036

3
[ 50998-17-9 ]
[ 97674-02-7 ]
[ 83570-42-7 ]

Reference： [1] Patent: US2005/256309, 2005, A1, . Location in patent: Page/Page column 35
[2] Patent: US2005/272736, 2005, A1, . Location in patent: Page/Page column 35
[3] Patent: WO2016/30443, 2016, A1, . Location in patent: Page/Page column 80
[4] Patent: WO2017/144633, 2017, A1, . Location in patent: Page/Page column 95
[5] Patent: WO2017/144639, 2017, A1, . Location in patent: Page/Page column 80

4
[ 3476-89-9 ]
[ 91-19-0 ]
[ 50998-17-9 ]
[ 76982-23-5 ]

Yield	Reaction Conditions	Operation in experiment
35%	With bromine In acetonitrile for 2.5 h; Reflux; Inert atmosphere	General procedure: Bromine was added dropwise to a magnetically stirred refluxing solution of quinoxaline (1) or tetrahydroquinoxaline 15 or 19 in the relevant solvent. The resulting reaction mixture was heated at reflux temperature. The reaction was monitored by TLC or ¹H NMR spectroscopy. After the desired time, the resulting reaction mixture was allowed to cool to room temperature and the solvent was removed under reduced pressure. The mixture was diluted with a saturated solution of sodium carbonate (10mL) and the mixture was extracted with ethyl acetate (2×25mL). Combined organic layers were washed with water, dried over Na₂SO₄ and concentrated. The crude was purified appropriate method described in below.

Reference： [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632

5
[ 34413-35-9 ]
[ 50998-17-9 ]
[ 76982-23-5 ]

Reference： [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632
[2] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632

6
[ 2423-66-7 ]
[ 50998-17-9 ]
[ 76982-23-5 ]

Reference： [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632
[2] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632

7
[ 528852-07-5 ]
[ 50998-17-9 ]
[ 76982-23-5 ]

Reference： [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632

8
[ 91-19-0 ]
[ 50998-17-9 ]
[ 76982-23-5 ]

Reference： [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632

9
[ 50998-17-9 ]
[ 201230-82-2 ]
[ 130345-50-5 ]

Reference： [1] Tetrahedron, 2007, vol. 63, # 27, p. 6252 - 6258

10
[ 50998-17-9 ]
[ 73183-34-3 ]
[ 1167418-13-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium acetate In 1,4-dioxane at 23 - 90℃;	Example 60. 6-Quinoxaline boronic acid, pinacol ester (S50)To 6-bromoquinoxaline (418 mg, 2.00 mmol, 1.00 equiv) in dioxane (10 niL) at 23 ⁰C was added PdCl2(dppf) -CH₂Cl₂ (163 mg, 0.200 mmol, 0.100 equiv), bis(pinacolato)diborone (610 mg, 2.40 mmol, 1.20 equiv), and KOAc (392 mg, 4.00 mmol, 2.00 equiv). After stirring for 1.5 hr at 90⁰C, the reaction mixture was cooled to 23 ⁰C and concentrated in vacuo. The residue was dissolved in CH₂Cl₂ and filtered through a plug of Celite. After the removal of CH₂Cl₂, the residue was purified by chromatography on silica gel eluting with hexanes/EtOAc 4:1 (v/v) to afford 500 mg of the title compound as a colorless solid (98percent yield).R/= 0.45 (hexanes/EtOAc 1:1 (v/v)). NMR Spectroscopy: ¹H NMR (500 MHz, CDCl₃, 23 ⁰C, δ): 8.86-8.82 (m, 2H), 8.59 (s, IH), 8.12 (dd, /= 8.0 Hz, 2.0 Hz, IH), 8.06 (d, / = 8.0 Hz, IH), 1.37 (s, 12H). ¹³C NMR (125 MHz, CDCl₃, 23 ⁰C, δ): 145.53, 145.03, 144.37, 142.41, 137.31, 134.75, 131.90 (br), 128.44, 84.36, 24.86. Mass Spectrometry: HRMS-FIA (m/z): Calcd for [M + H]⁺, 257.14558. Found, 257.14440.

Reference： [1] Organic Letters, 2009, vol. 11, # 13, p. 2860 - 2863
[2] Patent: WO2010/59943, 2010, A2, . Location in patent: Page/Page column 86
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4735 - 4751
[4] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[5] Organic Letters, 2018, vol. 20, # 6, p. 1530 - 1533
[6] Patent: CN105254613, 2016, A, . Location in patent: Paragraph 0095; 0096; 0097

[ 50998-17-9 ] Synthesis Path-Downstream 1~88

1
[ 50998-17-9 ]
[ 123-54-6 ]
[ 74-88-4 ]
[ 80827-21-0 ]
1-((3aR,9aS)-7-Bromo-2,9-dimethyl-3a,4,9,9a-tetrahydro-furo[2,3-b]quinoxalin-3-yl)-ethanone [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1981,vol. 17,p. 1129 - 1134
Khimiya Geterotsiklicheskikh Soedinenii,1981,vol. 17,p. 1543 - 1548

2
[ 50998-17-9 ]
[ 74-88-4 ]
7-Bromo-1-methyl-quinoxalin-1-ium; iodide [ No CAS ]
[ 80827-16-3 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1981,vol. 17,p. 1129 - 1134
Khimiya Geterotsiklicheskikh Soedinenii,1981,vol. 17,p. 1543 - 1548

3
[ 50998-17-9 ]
[ 329203-85-2 ]
6-(2-methyl-thiazol-4-ylethynyl)-quinoxaline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1080 - 1100

4
[ 50998-17-9 ]
[ 92136-39-5 ]
[ 892860-23-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3697 - 3711

5
[ 50998-17-9 ]
[ 201230-82-2 ]
[ 71-36-3 ]
butyl quinoxaline-6-carboxylate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 1255 - 1261

6
[ 50998-17-9 ]
[ 1002309-56-9 ]

Yield	Reaction Conditions	Operation in experiment
	With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene;tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; at 50℃; for 19h;	To a solution of <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (1.40 g, 7 mmol), tris (dibenzylideneacetone) dipalladium (o) (0.6 g, 0.7 mmol) and Q-phos (1.0 g) in 25 mL of THF was added Reactant 2 (27 ml, 27 mmol) three time in 3 hours. The reaction was heated at 50 oC for 16 hours and was quenched with 50 mL of satd. NH4C1. The mixture was diluted with 60 mL of EtOAc. The organic phase was separated, washed with brine, dried over Na2SO4 and concentrated in vacuo to give red oil. The residue was purified by a silica gel column chromatography (5% EtOAc/hex to EtOAC) twice to give red solid tert-butyl 2- (quinoxalin-6- yDacetate. MS (ESI, pos. ion) ra/zi 245.1 (M+l).

Reference： [1]Patent: WO2008/8539,2008,A2 .Location in patent: Page/Page column 120

7
[ 50998-17-9 ]
[ 7486-35-3 ]
[ 874279-33-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With lithium chloride;tetrakis(triphenylphosphine) palladium(0); In toluene; at 100℃; for 3h;	6-Vinyl-quinoxaline: A mixture of <strong>[50998-17-9]6-Bromo-quinoxaline</strong> (1.05 g, 5.02 mmol), palladium tetrakistriphenylphosphine (0.232 g, 0.2 mmol), and lithium chloride (0.639 g, 15.1 mmol) in dry toluene (50 mL) under nitrogen was treated with tributylvinyl tin (4.4 mL, 15.1 mmol) and heated to 100 C. for three hours. After cooling to room temperature the mixture was partitioned between ethyl acetate (200 mL) and water (100 mL). The aqueous layer was discarded and the organics washed with brine (2×100 mL), dried with magnesium sulfate, filtered, and concentrated to dryness on a rotary evaporator. Purification by flash column chromatography on silica gel using 10% ethyl acetate in dichloromethane as eluant yielded 680 mg (87% yield) of 6-Vinyl-quinoxaline as a light orange solid. 1H NMR (DMSO-d6): 8.92 (dd,2H,J=14.1,1.9 Hz), 8.10 (m,3H), 7.03 (dd,1H,J=17.7,10.9 Hz), 6.15 (dd,1H,J=17.7,0.4 Hz), 5.52 (d,1H,J=11.1 Hz). LC/MS (Method A): r.t.=1.14 min., purity=99%, calculated mass=156, [M+H]+=157.

Reference： [1]Patent: US2006/270848,2006,A1 .Location in patent: Page/Page column 37
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3845 - 3850
[3]Journal of the American Chemical Society,2011,vol. 133,p. 8467 - 8469

8
[ 50998-17-9 ]
[ 473895-88-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3845 - 3850

9
[ 50998-17-9 ]
[ 946619-95-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3845 - 3850

10
[ 50998-17-9 ]
C₃₇H₃₇F₄N₅O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3845 - 3850

11
[ 50998-17-9 ]
[ 860476-77-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3697 - 3711

12
[ 50998-17-9 ]
[ 892860-26-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3697 - 3711

13
[ 50998-17-9 ]
2-[4-ethyl-10-(3-hydroxy-6-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,8-trioxo-dodecahydro-1,3,5-trioxa-cyclopentacyclotetradecen-14-ylideneaminooxy]-<i>N</i>-(3-quinoxalin-6-yl-propyl)-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3697 - 3711

14
[ 50998-17-9 ]
C₄₅H₆₇N₅O₁₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3697 - 3711

15
[ 50998-17-9 ]
C₄₄H₆₅N₅O₁₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3697 - 3711

16
[ 50998-17-9 ]
C₄₄H₆₅N₅O₁₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3697 - 3711

17
[ 50998-17-9 ]
C₄₅H₆₇N₅O₁₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3697 - 3711

18
[ 50998-17-9 ]
C₄₆H₆₉N₅O₁₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3697 - 3711

19
[ 50998-17-9 ]
[ 860476-76-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3697 - 3711

20
[ 50998-17-9 ]
[ 892860-45-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3697 - 3711

21
[ 50998-17-9 ]
[ 892860-46-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3697 - 3711

22
[ 50998-17-9 ]
C₄₉H₆₃N₅O₁₁ [ No CAS ]

Reference： [1]Patent: US2004/14691,2004,A1 .Location in patent: Page 12

23
[ 50998-17-9 ]
[ 746668-81-5 ]
3-pyridin-2-yl-4-quinoxalin-6-yl-pyrazole-1-sulfonic acid dimethylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 85℃;	In a pressure tube was combined 425 mg (1. 4 mmol) 1- (N, N DIMETHYL)- SULFAMOYL-3-PYRIDIN-2-YL-PYRAZOLE-4-BORONIC acid, 200 mg (0. 95 mmol) 6- bromoquinoxaline, and 66 mg (0. 06 mmol, 6 mol%) OF TETRAKIS- (TRIPHENYLPHOSPHINE)- palladium (0), which were suspended in 6 mL of ethylene glycol dimethyl ether with stirring. To this reaction mixture was added 3 ML 1M NA2C03 solution before the pressure tube was capped and heated to 85 C. When the reaction mixture reached the desired temperature, it turned into a yellow solution, which was stirred overnight, allowed to cool, and diluted with ethyl acetate. The organic layer was washed 3x with 1N NAOH, then brine, dried (NA2S04), filtered and concentrated to a pale yellow solid. This solid was recrystallized from ethanol to give 260 mg (0. 68 mmol, 72%) OF 3- PYRIDIN-2-YL-4-QUINOXALIN-6-YL-PYRAZOLE-1-SULFONIC acid dimethylamide as fine, pale orange NEEDLES. 1H-NMR (300 MHz, CDC13, 6) : 8. 83 (s, 2 H), 8. 50 (dd, J = 0. 3 Hz, 4. 5 Hz, 1 H), 8. 26 (s, 1 H), 8. 13 (d, J = 1. 8 Hz, 1 H), 8. 04 (d, J = 8. 7 Hz, 1 H), 7. 90 (d, J = 7. 8 Hz, 1 H), 7. 77 (td, J = 1. 8 Hz, 7. 5 Hz, 2 H), 7. 29 (qd, J = 0. 9 Hz, 4. 8 Hz, 1 H), 3. 09 (s, 6H) ; M/Z : 381 [M + H] +.

Reference： [1]Patent: WO2004/72033,2004,A2 .Location in patent: Page 37

24
[ 50998-17-9 ]
[ 872090-71-6 ]
3-(1-cyano-1-methylethyl)-N-[4-methyl-3-(quinoxalin-6-ylamino)phenyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 15h;	Example 81; 3 -( 1 -Cvano- 1 -memylethy I)-JV- r4-methyl-3 -Cquinoxalin-o-ylaminolphenyllbenzamide; N-(3-Amino-4-methylphenyl)-3-(l-cyano-l-methylethyl)benzamide (Method 60; 0.150 g, 0.51 mmol), <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (0.109 g, 0.51 mmol), Pd2(dba)3 (0.024 g, 0.026 mmol), BINAP (0.032 g, 0.051 mmol), and sodium fert-butoxide (0.147 g, 1.53 mmol) were combined in toluene (3 ml) in a sealed tube under an argon atmosphere and heated to 100 0C for 15 hours. The reaction mixture was filtered over diatomaceous earth, concentrated and purified by reverse phase preparative HPLC. NMR (300 MHz): 10.24 (s, IH), 8.62 (d, IH), 8.51 (d, IH), 8.31 (s, IH), 7.94 (t, IH), 7.77 - 7.90 (m, 3H), 7.62 - 7.72 (m, IH), 7.48 - 7.58 (m, 2H), 7.45 (dd, 1.98, IH), 7.23 (d, IH), 7.02 (d, IH), 2.16 (s, 3H), 1.67 (s, 6H); m/z 422.

Reference： [1]Patent: WO2006/40568,2006,A1 .Location in patent: Page/Page column 54

25
[ 50998-17-9 ]
[ 913737-81-2 ]
[ 913737-82-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium t-butanolate;tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 1.5h;	vi) [(1R,3R)-3-(3-Chloro-phenylethynyl)-3-(4-methoxy-benzyloxy)-cyclohexyl]-quinoxalin-6-yl- amine: A solution of (1 R,3R)-3-(3-Chloro-phenylethynyl)-3-(4-methoxy-benzyloxy)- cyclohexylamine (34 mg), <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (23 mg), NaOt-Bu (13 mg), Pd2(dba)3 ' CHCI3 (1.9 mg) and BINAP (3.5 mg) in de-gassed toluene (2 ml) was stirred under Ar atmosphere for 1.5 h at 100. The mixture was distributed between cold 1 M Na2CO3 and EtOAc, the phases EPO <DP n="24"/>separated, the aqueous phase ectracted with EtOAc, the combined organic phases dried over Na2SO4 and evaporated. Chromatography afforded 38 mf of the desired product (83%).

Reference： [1]Patent: WO2006/114260,2006,A1 .Location in patent: Page/Page column 22-23

26
[ 131543-46-9 ]
[ 1575-37-7 ]
[ 50998-17-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	In methanol; water;	6-Bromo-quinoxaline: In a round bottom flask under nitrogen was combined 4-bromo-benzene-1,2-diamine (2.01 g, 10.7 mmol), methanol (50 mL), and glyoxal (40% by wt. 3.1 mL, 26.9 mmol) and the resulting solution stirred overnight. The reaction was then concentrated in vacuo and purified by flash column chromatography on silica gel using 5-10% ethyl acetate in dichloromethane as eluant to yield 1.14 g (50% yield) of 6-Bromo-quinoxaline as a yellow-orange solid. 1H NMR (DMSO-d6): 9.00 (d,2H,J=2.8 Hz), 8.36 (d,1H,J=2.2 Hz), 8.07 (d,1H,J=9.0 Hz), 8.02 (dd,1H,J=8.8,2.1 Hz). CHN for C8H5BrN2: calc. C 45.97, H 2.41, N 13.4; found C 45.99, H 2.09, N 13.09. LC/MS (Method A): r.t.=1.10 min., purity=99%, calculated mass=208, [M+H]+=209/211. HPLC (Method B): r.t.=7.4 min., purity=98.52% at 210-370 and 98.8% at 322 nm.
	In ethanol; water; for 10h;Heating / reflux;	To a solution of 4-bromobenzene-1, 2-diataunine (4.0 g, 21 mtnol) in 60 mL of EtOH was added 40% glyoxal aldehyde (4.1 ml, 32 mmol) soultion in water. The resulting mixture was refluxed for 10 hours. The mixture was concentrated in vacuo and the residue was diluted in 100 mLof EtOAc. The organic soultion was washed with 40 mL of satd. NaHCO3 and 40 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silca gel column chromatography (5% EtOAc/hex to EtOAC) to give light yellow solid 6-bromoquinoxaline. MS (ESI, pos . ion) m/z: 208.9 (M+l) .

Reference： [1]Patent: US2006/270848,2006,A1 .Location in patent: Page/Page column 37
[2]Patent: WO2008/8539,2008,A2 .Location in patent: Page/Page column 120

27
[ 50998-17-9 ]
[ 141-05-9 ]
diethyl-2-(6-quinoxalinyl)-2-butenedioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 100℃; for 16h;	Preparation 20: Diethyl-2-(6-quinoxalinyl)-2-butenedioate (P20)The title compound can be prepared through a palladium mediated coupling reaction, using diethyl maleate or fumarate as a common reagent (e.g. Tetrahedron, 2002, 58,6545). For example, a mixture of <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (1 eq.), diethyl maleate (2.3 eq.), palladium acetate (0.05 eq.), tri(o-tolyl)phosphine (0.1 eq.) and potassium carbonate (2 eq.) in DMF may be warmed to 100 0C and stirred for 16 hours. Quenching with water, extraction with diethyl ether and purification of the crude product by flash chromatography should provide the title compound.

Reference： [1]Patent: WO2007/22933,2007,A1 .Location in patent: Page/Page column 38

28
[ 50998-17-9 ]
[ 201733-56-4 ]
[ 946501-49-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 110℃; for 4h;	Step 2: 6-(5,5-Dimcthyl-l,3,2-dioxaborinan-2-yl)quinoxalinc (E2)A mixture of <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (1.0 eq.), bis-(neopentylglycolato)diborane (1.1 eq.), KOAc (3.0 eq.) and Pd(dppf)Cl2 (0.05 eq.) in 1,4-dioxane was degassed with a stream of Ar for 10 minutes and then heated at 11O0C for 4 hrs. The reaction mixture was concentrated and the residue used in the next step without further purification. MS (ES) Ci3H5BN2O2 requires: 242, found: 175 (M-[C5Hi0] +H+).

Reference： [1]Patent: WO2007/93827,2007,A1 .Location in patent: Page/Page column 47

29
[ 50998-17-9 ]
[ 109-54-6 ]
[ 1003194-24-8 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 5529 - 5532

30
[ 50998-17-9 ]
[ 50846-01-0 ]
[ 1003194-30-6 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 5529 - 5532

31
[ 50998-17-9 ]
[ 107-18-6 ]
[ 1029715-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Methyldicyclohexylamine;tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; at 40℃;	A mixture of <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (0.40 g, 1.9 mmol), 2-propen-l-ol (0.260 mL, 3.8 mmol), tris(dibenzylideneacetone)dipalladium (26 mg, 0.029 mmol), tri-tert-butylphosphonium tetrafluoroborate (16 mg, 0.057 mmol) and N-cyclohexyl-N-methyl-cyclohexanamine (0.49 mL, 2.3 mmol) in 1,4-dioxane (3.0 mL) was stirred at 40 0C overnight. After cooling to RT, the mixture was filtered, washed with methylene chloride and the filtrate was concentrated. The crude material was purified by chromatography on silica gel with EtOAc in Hexane (0-40%) to afford the desired product (195 mg). LCMS: (M+H) = 187.3.

Reference： [1]Patent: WO2008/64157,2008,A1 .Location in patent: Page/Page column 81

32
[ 50998-17-9 ]
[ 5350-57-2 ]
[ 1020173-84-5 ]

Yield	Reaction Conditions	Operation in experiment
20%		Example B28 In toluene (8 mL) was placed 1-(diphenylmethylene)hydrazine (1.00 g, 5.10 mmol), palladium acetate (10.4 mg, 0.0464 mmol) and 2-(diphenylphosphino)-1-(2-(diphenylphosphino)naphthalen-1-yl)naphthalene (44 mg, 0.0696 mmol) and the reaction was stirred at 100 C. under Ar for 5 min and then cooled to RT. To this dark purple solution was added <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (970 mg, 4.64 mmol), sodium t-butoxide (624 mg, 6.50 mmol) and toluene (2 mL). The reaction was placed under Ar and warmed to 100 C. for 5 hrs, cooled to RT and stirred overnight. The reaction was diluted with ether (50 mL) and water (30 mL) and filtered through a Celite pad. The pad was washed with ether (20 mL) and water (20 mL). The combined organic layers were washed with brine (50 mL), dried (Na2SO4), concentrated in vacuo and purified by chromatography (ethyl acetate/hexanes) to give 1-(diphenylmethylene)-2-(quinoxalin-6-yl)hydrazine (305 mg, 20% yield) as a bright yellow foam. 1H NMR (300 MHz, DMSO-d6) delta 7.35-7.41 (m, 5H), 7.51-7.53 (m, 2H), 7.58-7.65 (m, 3H), 7.75 (s, 1H), 7.89 (s, 2H), 8.61 (s, 1H), 8.74 (s, 1H), 9.60 (s, 1H); MS (ESI) m/z: 325.0 (M+H+).
20%	With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 100℃; for 5h;Inert atmosphere;	In toluene (8 mL) was placed 1- (diphenylmethylene)hydrazine (1.00 g, 5.10 mmol), palladium acetate (10.4 mg, 0.0464 mmol) and 2-(diphenylphosphino)- 1 -(2-(diphenylphosphino)naphthalen- 1 -yl)naphthalene (44 mg, 0.0696 mmol) and the reaction was stirred at 100 C under Ar for 5 min and then cooled to RT. To this dark purple solution was added <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (970 mg, 4.64 mmol), sodium t-butoxide (624 mg, 6.50 mmol) and toluene (2 mL). The reaction was placed under Ar and warmed to 100 C for 5 hrs, cooled to RT and stirred overnight. The reaction was diluted with ether (50 mL) and water (30 mL) and filtered through a Celite pad. The pad was washed with ether (20 mL) and water (20 mL). The combined organic layers were washed with brine (50 mL), dried (Na2SC>4), concentrated in vacuo and purified by chromatography (ethyl acetate/hexanes) to give l-(diphenylmethylene)-2- (quinoxalin-6-yl)hydrazine (305 mg, 20% yield) as a bright yellow foam. FontWeight="Bold" FontSize="10" H NMR (300 MHz, DMSO-i/e) delta 7.35-7.41 (m, 5 H), 7.51-7.53 (m, 2 H), 7.58-7.65 (m, 3 H), 7.75 (s, 1 H), 7.89 (s, 2 H), 8.61 (s, 1 H), 8.74 (s, 1 H), 9.60 (s, 1 H); MS (ESI) m/z: 325.0 (M+H+).

Reference： [1]Patent: US2008/90856,2008,A1 .Location in patent: Page/Page column 48
[2]Patent: WO2013/36232,2013,A2 .Location in patent: Paragraph 00347

33
[ 50998-17-9 ]
[ 375853-82-0 ]
[ 1093065-07-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; ethanol; water; at 160℃; for 0.25h;Microwave irradiation;	A solution containing <strong>[50998-17-9]6-bromo-quinoxaline</strong> (417 mg, 2.0 mmol), 4-(4,4,5,5- tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert- butyl ester (600 mg, 1.94 mmol), tetrakis [triphenylphosphine] palladium (108 mg, 0.1 mmol) and sodium carbonate (2 M solution, 3 mL) in 5 ml_ of dioxane/ethanol/water <n="265"/>(7:3:1 ) was heated at 160 C using microwave reactor for 15 minutes. After the reaction, ethylacetate was added and the mixture was filtered, washed with water. After concentration under vacuum, the product was purified using column chromatography (5% methanol in dichloromethane)
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; ethanol; water; at 160℃; for 0.25h;Microwave irradiation;	A solution containing <strong>[50998-17-9]6-bromo-quinoxaline</strong> (417 mg, 2.0 mmol), 4-(4 ,4,5,5- tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert- butyl ester (600 mg, 1.94 mmol), tetrakis [triphenylphosphine] palladium (108 mg, 0.1 mmol) and sodium carbonate (2 M solution, 3 ml_) in 5 ml_ of dioxane/ethanol/water (7:3:1 ) was heated at 160 C using microwave reactor for 15 minutes. After the reaction, ethylacetate was added and the mixture was filtered, washed with water. After concentration under vacuum, the product was purified using column chromatography (5% methanol in dichloromethane)

Reference： [1]Patent: WO2008/156739,2008,A1 .Location in patent: Page/Page column 263-264
[2]Patent: WO2008/153858,2008,A1 .Location in patent: Page/Page column 308

34
[ 50998-17-9 ]
[ 201230-82-2 ]
[ 98-80-6 ]
[ 92060-44-1 ]
phenyl-quinoxalin-6-yl methanone [ No CAS ]

Reference： [1]Chemistry - A European Journal,2008,vol. 14,p. 3645 - 3652
[2]Chemistry - A European Journal,2008,vol. 14,p. 3645 - 3652

35
[ 50998-17-9 ]
[ 1131040-38-4 ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 457 - 468

36
[ 50998-17-9 ]
[ 3282-30-2 ]
[ 1131040-35-1 ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 457 - 468

37
[ 50998-17-9 ]
[ 98-88-4 ]
[ 1131040-36-2 ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 457 - 468

38
[ 50998-17-9 ]
[ 73183-34-3 ]
[ 1167418-13-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 23 - 90℃;	Example 60. 6-Quinoxaline boronic acid, pinacol ester (S50)To <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (418 mg, 2.00 mmol, 1.00 equiv) in dioxane (10 niL) at 23 0C was added PdCl2(dppf) -CH2Cl2 (163 mg, 0.200 mmol, 0.100 equiv), bis(pinacolato)diborone (610 mg, 2.40 mmol, 1.20 equiv), and KOAc (392 mg, 4.00 mmol, 2.00 equiv). After stirring for 1.5 hr at 900C, the reaction mixture was cooled to 23 0C and concentrated in vacuo. The residue was dissolved in CH2Cl2 and filtered through a plug of Celite. After the removal of CH2Cl2, the residue was purified by chromatography on silica gel eluting with hexanes/EtOAc 4:1 (v/v) to afford 500 mg of the title compound as a colorless solid (98% yield).R/= 0.45 (hexanes/EtOAc 1:1 (v/v)). NMR Spectroscopy: 1H NMR (500 MHz, CDCl3, 23 0C, delta): 8.86-8.82 (m, 2H), 8.59 (s, IH), 8.12 (dd, /= 8.0 Hz, 2.0 Hz, IH), 8.06 (d, / = 8.0 Hz, IH), 1.37 (s, 12H). 13C NMR (125 MHz, CDCl3, 23 0C, delta): 145.53, 145.03, 144.37, 142.41, 137.31, 134.75, 131.90 (br), 128.44, 84.36, 24.86. Mass Spectrometry: HRMS-FIA (m/z): Calcd for [M + H]+, 257.14558. Found, 257.14440.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 2h;Inert atmosphere;	The A8-1 (63mg, 0.30mmol) was dissolved in dioxane (6mL), bis (pinacolato) borate (91mg, 0.36mmol), KOAc (59mg,0.60mmol), Pd (dppf) 2Cl2 (25mg, 0.03mmol), purged with nitrogen, 90 stirred for 2 hours, cooled to room temperature, suction filtered through Celite, the filterLiquid spin dry to give crude black oil (160mg), was used directly in the next step.

Reference： [1]Organic Letters,2009,vol. 11,p. 2860 - 2863
[2]Patent: WO2010/59943,2010,A2 .Location in patent: Page/Page column 86
[3]Journal of Medicinal Chemistry,2011,vol. 54,p. 4735 - 4751
[4]Journal of the American Chemical Society,2017,vol. 139,p. 8267 - 8276
[5]Organic Letters,2018,vol. 20,p. 1530 - 1533
[6]Patent: CN105254613,2016,A .Location in patent: Paragraph 0095; 0096; 0097

39
[ 50998-17-9 ]
[ 107-19-7 ]
[ 545421-71-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In acetonitrile; at 80℃; for 18h;Inert atmosphere;	To <strong>[50998-17-9]6-bromo-quinoxaline</strong> (1 g) in acetonitrile (25 mL) was added propargyl alcohol (0.285 mL) and triethylamine (1.334 mL) followed by copper(I) iodide (10 mg) and bis(triphenylphosphine)palladium chloride (34 mg). The reaction mixture was stirred under nitrogen and then heated at 800C for 18h. The mixture was allowed to cool and then filtered. The filtrate was evaporated and then purified by chromatography on silica eluting with ethylacetate / isohexane (1 : 1 to 1 : 0) to afford the sub-titled compound as a solid (0.7 g).1H NMR (400 MHz, DMSO) I' 8.97 (2H, dd), 8.13 (IH, d), 8.10 (IH, d), 7.84 (IH, dd), 5.45 (IH, t), 4.39 (2H, d).

Reference： [1]Patent: WO2009/153536,2009,A1 .Location in patent: Page/Page column 68

40
[ 5305-59-9 ]
[ 50998-17-9 ]
[ 852062-32-9 ]

Yield	Reaction Conditions	Operation in experiment
		Description 137; 6-Quinoxalin-6-vlpvrimidin-4-amine; 6-Bromoquinoxaline (210 mg, 1.44 mmol), potassium acetate (141 mg, 1.44 mmol), bis (pinacolato) diboron (383 mg, 1.51 mmol) and [1, 1'- bis (diphenylphosphino) ferrocene] palladium (II) chloride (52 mg, 0.072 mmol) were suspended in dioxane (10 ml) and heated to 100C for 16 hours. 4-Amino-6- chloropyrimidine [WO-A-0245652] (186 mg, 1.44 mmol), [l, 1'- bis (diphenylphosphino) ferrocene]-palladium (II) chloride (52 mg, 0.072 mmol) and 2M Na2CO3 (aq) (2ml) were added and the mixture was heated at 100 oC for a further 16 hours. The mixture was partitioned between EtOAc and water, the aqueous phase was extracted with EtOAc, the combined organic phases were washed (brine), dried (sodium sulfate) and concentrated under reduced pressure. The residue was triturated with EtOAc to give a white solid, which was used in the next step without purification (170 mg).

Reference： [1]Patent: WO2005/47279,2005,A1 .Location in patent: Page/Page column 61

41
[ 50998-17-9 ]
[ 1031432-89-9 ]
[ 1186108-02-0 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 100℃; for 1h;Inert atmosphere;	Example 13l-ethyl-3-(5-(quinoxalin-6-yl)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-2-yl)ureaA reaction mixture of l-ethyl-3-(5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-4-(4- (trifluoromethyl)thiazol-2-yl)pyridin-2-yl)urea (Intermediate 12, 100 mg, 0.23 mmol), 6- bromoquinoxaline (43.0 mg, 0.21 mmol),Tetrakis (23.75 mg, 0.02 mmol), and cesium carbonate (73.7 mg, 0.23 mmol) in dioxane and water was prepared. The reaction mixture was degassed with nitrogen for 15 minutes and then heated to 100 0C for 1 h. The reaction mixture was partitioned between methylene chloride and water. The organic layer was washed with saturated sodium chloride, dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by flash column chromatogrpahy (silica, 15:1 methylene chloride/methanol) gave 44 mg of desired product.MS (ESP): 445 (M+ 1) for C20H15F3N6OS.1H NMR (300 MHz, DMSO-J6): 1.12 (t, J = 7 Hz, 3H), 3.24 (m, 2H), 7.23 (m, IH), 7.43 (m, IH), 8.04 (m, IH), 8.21 (m, IH), 8.36 (m, IH), 8.55 (m, IH), 9.02 (br s, 2H), 9.36 (s, IH), 9.52 (s, IH).
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 1h;Inert atmosphere;	Example 13 l-ethyl-3-(5-(quinoxalin-6-yl)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-2-yl)urea A reaction mixture of l-ethyl-3-(5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-4-(4- (trifluoromethyl)thiazol-2-yl)pyridin-2-yl)urea (Intermediate 12, 100 mg, 0.23 mmol), 6- bromoquinoxaline (43.0 mg, 0.21 mmol),Tetrakis (23.75 mg, 0.02 mmol), and cesium carbonate (73.7 mg, 0.23 mmol) in dioxane and water was prepared. The reaction mixture was degassed with nitrogen for 15 minutes and then heated to 100 0C for 1 h. The reaction mixture was partitioned between methylene chloride and water. The organic layer was washed with saturated sodium chloride, dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by flash column chromatogrpahy (silica, 15:1 methylene chloride/methanol) gave 44 mg of desired product. MS (ESP): 445 (M+ 1) for C20Hi5F3N6OS. 1H NMR (300 MHz, DMSO-J6): 1.12 (t, J = 7 Hz, 3H), 3.24 (m, 2H), 7.23 (m, IH), 7.43 (m, IH), 8.04 (m, IH), 8.21 (m, IH), 8.36 (m, IH), 8.55 (m, IH), 9.02 (br s, 2H), 9.36 (s, IH), 9.52 (s, IH).

Reference： [1]Patent: WO2011/24004,2011,A1 .Location in patent: Page/Page column 62-63
[2]Patent: WO2009/106885,2009,A1 .Location in patent: Page/Page column 66

42
[ 50998-17-9 ]
[ 64-18-6 ]
[ 1219715-68-0 ]
[ 1348788-56-6 ]

Yield	Reaction Conditions	Operation in experiment
		A degassed mixture of the crude 3-(3-pyrrolidin-1-yl-prop-1-ynyl)-2-trimethylstannanyl-imidazo[1,2-a]pyridine-6-carboxylic acid bis-(3-methyl-butyl)amide (ca. 262 mg) and <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (96 mg) in DMF (3 ml) was treated with Pd(PPh3)4 (48 mg). The reaction mixture was transferred to a pre-heated oil bath (110C) and stirred in a sealed tube at this temperature for 18 h. The mixture was diluted with diethyl ether (25 ml) and washed with water (1 x 20 ml). The aqueous layer was extracted with diethyl ether (2 x 15 ml). The combined organic extracts were washed with brine (30 ml), dried over sodium sulfate, filtered, and evaporated. The crude product was isolated by column chromatography and re-purified by preparative HPLC-MS.

Reference： [1]Patent: EP2168965,2010,A1 .Location in patent: Page/Page column 34

43
[ 50998-17-9 ]
3-acetylphenylboronic acid [ No CAS ]
[ 1225280-51-2 ]

Yield	Reaction Conditions	Operation in experiment
> 95%	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 110℃; for 18h;Product distribution / selectivity;	EXAMPLE 622,5-Dimethyl-5-[3-(quinoxalin-6-yl)phenyl1tetrahydrofuran-2-ol6-Bromoquinoxaline (3.14 g, 15 mmol) was dissolved in DME/water (9:1, 500 niL), and 3-acetylphenylboronic acid (2.5 g, 15 mmol), cesium carbonate (9.75 g, 30 mmol) and Pd(PPh3 )4 (870 mg, 0.75 mmol) were added. The mixture was heated to 1100C for 18 h. After cooling, the mixture was partitioned between EtOAc and water (100 mL each), and the organic phase concentrated in vacuo. The residue was triturated with diethyl ether (50 mL) to give l-[3-(quinoxalin-6-yl)phenyl]ethanone (3.8 g, >95%). LCMS (ES+) 249.2 (M+H)+, RT 3.04 minutes. A sample of this material (500 mg, 2 mmol) was dissolved in THF (4 mL), and cooled to O0C. But-l-en-4-ylmagnesium bromide (0.5M in THF, 4 mL, 2 mmol) was added and the mixture allowed to warm to room temperature. After stirring for 2 h, water (2 mL) was added. The organic phase was passed though a silica plug and concentrated in vacuo. The residue was dissolved in DCM (3 mL). 7V-Bromosuccinimide (146 mg, 0.9 mmol) was added and the mixture stirred at room temperature for 18 h. The mixture was partitioned between DCM (5 mL) and saturated sodium hydrogencarbonate solution (5 mL). The organic phase was passed through a silica plug and the filtrate concentrated in vacuo. The residue was dissolved in MeOH (3 mL). Sodium methoxide (200 mg) was added and the mixture was stirred at 600C for 3 days. The mixture was neutralized to pH 7.0 with IM hydrochloric acid and then concentrated in vacuo. The residue was purified by preparative HPLC to isolate the title compound (5 mg, 2:1 mixture of cis:trans isomers). deltaH (CDCl3) 8.89 (d, IH), 8.86 (d, IH), 8.32 (m, IH), 8.20 (m, IH), 8.08 (m, IH), 7.84 (m, IH), 7.62 (m, IH), 7.50 (m, 2H), 2.10-2.58 (m, 4H), 2.11 (s, 3H), 1.56-1.72 (m, 4H). LCMS (ES+) 321.3 (M+H)+, RT 2.93 minutes.

Reference： [1]Patent: WO2010/52448,2010,A2 .Location in patent: Page/Page column 84

44
[3-(aminomethyl)phenyl]boronic acid hydrochloride [ No CAS ]
[ 50998-17-9 ]
[ 24424-99-5 ]
[ 1225280-29-4 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 121fert-Butyl 3-(quinoxalin-6-yl)benzylcarbamate6-Bromoquinoxaline (500 mg, 2.39 mmol), 3-(aminomethyl)phenylboronic acid hydrochloride (445 mg, 2.39 mmol), potassium phosphate (1000 mg, 4.78 mmol), water (3 mL), DME (13 mL) and Pd(PPh3)4 (277 mg, 0.24 mmol) were combined in a sealed tube and heated under microwave irradiation to 1400C for 1 h. Di-tert-butyl dicarbonate (545 mg, 2.50 mmol) was then added and the reaction mixture stirred at room temperature for 18 h. The organic layer was concentrated to dryness and purified by chromatography (SiO2, 20-100% EtOAc in petroleum ether) to give a yellow gum (232 mg). A sample (30 mg) was further purified by preparative HPLC to give the title compound (21.6 mg) as a clear solid. deltaH (CDCl3) 8.88 (IH, d, J 1.85 Hz), 8.85 (IH, d, J 1.86 Hz), 8.31 (IH, d, J 2.05 Hz), 8.18 (IH, d, J 8.73 Hz), 8.05 (IH, dd, J 8.74, 2.08 Hz), 7.67 (2H, d, J6.92 Hz), 7.49 (IH, t, J7.84 Hz), 7.37 (IH, d, J7.61 Hz), 4.93 (IH, s), 4.44 (2H, d, J5.95 Hz), 1.48 (9H, s). LCMS (ES+) 336 (M+H)+, RT 3.58 minutes {Method 2).

Reference： [1]Patent: WO2010/52448,2010,A2 .Location in patent: Page/Page column 107

45
[3-(aminomethyl)phenyl]boronic acid hydrochloride [ No CAS ]
[ 50998-17-9 ]
[ 1225279-82-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 140℃; for 1h;Sealed tube; Microwave irradiation;	EXAMPLE 79[3-(Quinoxalin-6-yl)phenyl]methanamine, formic acid salt6-Bromoquinoxaline (100 mg, 0.48 mmol), 3-(aminomethyl)phenylboronic acid hydrochloride (89 mg, 0.48 mmol), potassium phosphate (100 mg, 0.48 mmol), water (2 mL), DME (6 mL) and Pd(PPh3)4 (55 mg, 0.048 mmol) were combined in a sealed tube and heated under microwave irradiation to 1400C for 1 h. After cooling, the mixture was filtered through Celite. The filtrate was then concentrated to dryness and purified by preparative HPLC to give the title compound (17.7 mg, 16%) as a tan solid. deltaH (DMSO- <h) 9.00 (IH, d, J 1.86 Hz), 8.96 (IH, d, J 1.86 Hz), 8.39 (IH, d, J 1.96 Hz), 8.34 (IH, s, HCOOH), 8.24 (IH, dd, J 8.78, 2.03 Hz), 8.22-8.18 (IH, m), 7.97 (IH, t, J 1.69 Hz), 7.82 (IH, dt, J 7.62, 1.47 Hz), 7.53 (IH, t, J7.60 Hz), 7.47 (IH, d, J 7.63 Hz), 3.97 (2H, s), 2 NH not visible. LCMS (ES+) 236 (M+H)+, RT 2.09 minutes {Method 1).

Reference： [1]Patent: WO2010/52448,2010,A2 .Location in patent: Page/Page column 90-91

46
[ 50998-17-9 ]
[ 458532-96-2 ]
[ 1225280-57-8 ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 120℃; for 0.333333h;Sealed tube; Microwave irradiation;	INTERMEDIATE 216-(2-Chloropyridin-4-yl)quinoxalineA mixture of <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (1.07 g, 5.14 mmol), 2-chloropyridine-4- boronic acid (810 mg, 5.14 mmol), 2M aqueous sodium carbonate solution (5.5 mL, 11 mmol) and Pd(PPh3)4 (178 mg, 0.15 mmol) in DME (11 mL) was heated to 1200C in a sealed tube, under microwave irradiation, for 20 minutes. After cooling, the mixture was partitioned between water and EtOAc (100 mL each). The aqueous phase was extracted with EtOAc/THF (4: 1, 50 mL). The combined organic phases were dried (MgSO4) and concentrated in vacuo. The residue was washed with diethyl ether/THF (9: 1, 30 mL) to give the title compound (790 mg, 64%) as a brown solid. deltaH (CDCl3) 8.89-8.97 (m, 2H), 8.54 (d, IH), 8.39 (d, IH), 8.26 (d, IH), 8.03 (dd, IH), 7.72 (s, IH), 7.60 (dd, IH). LCMS (ES+) 242 (M+H)+, RT 2.87 minutes.

Reference： [1]Patent: WO2010/52448,2010,A2 .Location in patent: Page/Page column 42

47
[ 50998-17-9 ]
[ 1021186-08-2 ]
[ 1225278-95-4 ]

Yield	Reaction Conditions	Operation in experiment
56%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 120℃; for 0.333333h;Sealed tube; Microwave irradiation;	EXAMPLE 1; 6-[3-(Piperidin-l-ylmethvDphenyllquinoxalineA mixture of <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (42 mg, 0.2 mmol), 3-(piperidin-l-ylmethyl)- phenylboronic acid pinacol ester hydrochloride (67 mg, 0.21 mmol), 2M aqueous sodium carbonate solution (0.3 mL, 0.6 mmol) and Pd(PPh3 )4 (7 mg, 0.006 mmol) in DME (0.6 mL) was heated to 12O0C in a sealed tube, under microwave irradiation, for 20 minutes. After cooling, the mixture was partitioned between saturated ammonium chloride solution and EtOAc (2 mL each), and the organic phase concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (34 mg, 56%) as a pale yellow- brown gum. deltaH (CDCl3) 8.88 (d, IH), 8.85 (d, IH), 8.33 (d, IH), 8.19 (d, IH), 8.08 (dd, IH), 7.75 (s, IH), 7.68 (d, IH), 7.48 (t, IH), 7.41 (d, IH), 3.69 (s, 2H), 2.46-2.63 (m, 4H), 1.59-1.72 (m, 4H), 1.40-1.53 (m, 2H). LCMS (ES+) 304 (M+H)+, RT 2.49 minutes.

Reference： [1]Patent: WO2010/52448,2010,A2 .Location in patent: Page/Page column 52

48
[ 50998-17-9 ]
[ 87199-16-4 ]
[ 1225280-50-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 120℃; for 0.333333h;Sealed tube; Microwave irradiation;	INTERMEDIATE 13 -(Quinoxalin-6-yl)benzaldehydeA mixture of <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (210 mg, 1.01 mmol), 3-formylphenylboronic acid (301 mg, 2.01 mmol), 2M aqueous sodium carbonate solution (1.7 mL, 14.4 mmol) and Pd(PPh3)4 (35 mg, 0.03 mmol) in DME (3.5 mL) was heated to 1200C in a sealed tube, under microwave irradiation, for 20 minutes. After cooling, the organic phase was adsorbed onto silica and purified by column chromatography (SiO2, 10-100% EtOAc in heptane) to give the title compound (340 mg) as a beige solid. 6H (CDCl3) 10.15 (s, IH), 8.91 (d, IH), 8.89 (d, IH), 8.38 (d, IH), 8.26-8.31 (m, IH), 8.24 (d, IH), 8.10 (dd, IH), 8.02-8.07 (m, IH), 7.94-8.00 (dd, IH), 7.72 (t, IH). LCMS (ES+) 235 (M+H)+, RT 2.99 minutes.

Reference： [1]Patent: WO2010/52448,2010,A2 .Location in patent: Page/Page column 34

49
[ 350-03-8 ]
[ 50998-17-9 ]
[ 1213251-60-5 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 1032 - 1035

50
[ 50998-17-9 ]
[ 1268852-77-2 ]
C₂₅H₂₉Cl₂N₃Si [ No CAS ]

Reference： [1]Synthesis,2010,p. 4075 - 4081

51
[ 50998-17-9 ]
[ 1305318-35-7 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 8467 - 8469

52
[ 50998-17-9 ]
[ 100073-15-2 ]
[ 1305318-41-5 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 8467 - 8469

53
[ 50998-17-9 ]
[ 71-43-2 ]
[ 92060-44-1 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 3556 - 3559

54
[ 50998-17-9 ]
[ 1201841-71-5 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4735 - 4751

55
[ 50998-17-9 ]
[ 5407-04-5 ]
[ 1003194-24-8 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 8891 - 8906

56
[ 50998-17-9 ]
[ 201230-82-2 ]
[ 870-24-6 ]
C₁₁H₉N₃O [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13619 - 13623

57
[ 50998-17-9 ]
[ 909135-34-8 ]
C₂₁H₂₅N₃O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 9929 - 9945

58
[ 50998-17-9 ]
[ 1422465-08-4 ]
[ 1422465-18-6 ]

Yield	Reaction Conditions	Operation in experiment
19%	With tetrabutylammonium acetate; palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 100℃; for 13h;	To a solution of 11i (30 mg, 110 mumol), <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (41.8 mg, 200 mumol), Bu4NOAc (78.3 mg, 260 mumol) and Pd(OAc)2 (4.4 mg, 19.6 mol) in NMP (0.5 mL ). The reaction mixture was stirred for 13 h at 100 oC and cooled to room temperature. The mixture was concentrated under reduced pressure, diluted with water, and extracted with EtOAc (3 × 5 mL). The EtOAc solution was washed with brine (5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 hexane/EtOAc) to afford the compound 12i (8.4 mg, 19%) as a yellow solid. TLC: Rf 0.29 (1:1 hexane/EtOAc). mp: 164166 oC. 1H-NMR (400 MHz, CDCl3) delta 8.93 (d, 1H, J = 2.0 Hz), 8.88 (d, 1H, J = 2.0 Hz), 8.18 (d, 1H, J = 8.8 Hz), 8.08 (d, 1H, J = 2.0 Hz), 7.77 (dd, 1H, J = 8.8 Hz, J = 2.0 Hz), 7.74 (t, 1H, J = 8.0 Hz), 7.65 (d, 1H, J = 8.0 Hz), 7.15-7.10 (m, 3H), 6.73 (tt, 1H, JHF = 8.8 Hz, JHH = 2.4 Hz), 2.17 (s, 3H). 13C-NMR (100 MHz, CDCl3) delta 163.3 (dd, JCF = 246.9 Hz, JCF = 13.1 Hz), 158.4, 148.9, 146.3, 146.0, 144.0, 143.2, 142.8, 139.3, 133.6, 133.2, 132.3, 131.7, 130.3, 130.0, 124.0, 115.6, 110.5 (dd, JCF = 19.3 Hz, JCF = 7.6 Hz), 103.9 (t, JCF = 24.9 Hz), 23.8. HRMS (ESI) calcd. for C22H15F2N6 (M+H): 401.1321; found 401.1327.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1083 - 1086

59
[ 50998-17-9 ]
[ 1422465-09-5 ]
[ 1422465-19-7 ]

Yield	Reaction Conditions	Operation in experiment
35%	With tetrabutylammonium acetate; palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 100℃; for 11h;	To a solution of 11j (30 mg, 120 mumol), <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (37.6 mg, 180 mumol), Bu4NOAc (72.2 mg, 23.9 mumol) and Pd(OAc)2 (4.0 mg, 17.8 mol) in NMP (0.5 mL ). The reaction mixture was stirred for 11 h at 100 oC and cooled to room temperature. The mixture was concentrated under reduced pressure. Diluted with water and extracted with EtOAc (3 × 5 mL). The EtOAc solution was washed with brine (5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 hexane/EtOAc) to afford the compound 12j (15.8 mg, 35%) as a pale yellow solid. TLC: Rf 0.41 (1:1 hexane/EtOAc). mp: 188190 oC. 1H-NMR (400 MHz, CDCl3) delta 8.89 (d, 1H, J = 1.6 Hz), 8.85 (d, 1H, J = 1.6 Hz), 8.11 (d, 1H, J = 8.8 Hz), 8.07 (d, 1H, J = 1.6 Hz), 7.76 (dd, 1H, J = 8.8 Hz, J = 1.6 Hz), 7.73 (t, 1H, J = 8.0 Hz), 7.63 (d, 1H, J = 8.0 Hz), 7.47 (d, 2H, J = 8.0 Hz), 7.13-7.08 (m, 3H), 2.32 (s, 3H), 2.19 (s, 3H). 13C-NMR (100 MHz, CDCl3) delta 158.3, 149.2, 146.3, 145.9, 145.8, 143.0, 142.8, 139.1, 138.4, 132.7, 132.1, 131.6, 131.2, 129.5, 128.8, 127.8, 127.5, 123.7, 115.7, 23.8, 21.4. HRMS (ESI) calcd. for C23H19N6 (M+H): 379.1666; found 379.1671

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1083 - 1086

60
[ 50998-17-9 ]
[ 1224886-21-8 ]
[ 1422465-20-0 ]

Yield	Reaction Conditions	Operation in experiment
22%	With tetrabutylammonium acetate; palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 100℃; for 22h;	11k (100 mg, 400 mol), <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (125 mg, 600 mumol), Bu4NOAc (241 mg, 799 mol) and Pd(OAc)2 (4.5 mg, 20.0 mol) were dissolved in NMP (1.6 mL ). The reaction mixture was stirred at 100 oC for 22 h and cooled to room temperature. The mixture was quenched with water (10 ml) treated with saturated aqueous NaHCO3 solution (3 ml), and extracted with EtOAc (3 × 30 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated by rotary evaporation. The residue was purified by column chromatography (1:1.5 hexane/EtOAc) to afford the compound 12k (33.4 mg, 22%) as a yellow solid. TLC: Rf 0.33 (1:1 hexane/EtOAc). mp: 112.5114.5 oC. 1H-NMR (400 MHz; CDCl3) delta 8.89 (d, 1H, J = 1.6 Hz), 8.88 (d, 1H, J = 1.6 Hz), 8.04 (d, 1H, J = 8.8 Hz), 8.01 (d, 1H, J = 1.6 Hz), 7.72 (t, 1H, J = 7.6 Hz), 7.62 (d, 1H, J = 7.6 Hz), 7.55 (dd, 1H, J = 8.8 Hz, J = 1.6 Hz), 7.26-7.14 (m, 5H), 7.11 (d, 1H, J = 7.6 Hz), 4.17 (s, 2H), 2.17 (s, 3H). 13C-NMR (100 MHz; CDCl3) delta 158.3, 149.2, 146.2, 145.9, 145.8, 142.8, 142.7, 139.2, 138.9, 133.4, 132.2, 130.7, 130.6, 129.2, 128.8, 128.7, 126.6, 123.6, 115.2, 31.4, 23.8. HRMS (ESI) calcd. for C23H19N6 (M+H): 379.1666; found 379.1662.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1083 - 1086

61
[ 50998-17-9 ]
[ 1422465-01-7 ]
[ 1422465-10-8 ]

Yield	Reaction Conditions	Operation in experiment
19%	With tetrabutylammonium acetate; palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 100℃; for 4h;	To a solution of 11a (108 mg, 499 mumol), <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (157 mg, 751 mumol), Bu4NOAc (302 mg, 1.00 mmol) and Pd(OAc)2 (17 mg, 75.7 mumol) in NMP (1 mL). The reaction mixture was stirred for 4 h at 100 oC and cooled to room temperature. The mixture was concentrated under reduced pressure, diluted with water and extracted with EtOAc (3 × 5 mL). The EtOAc solution was washed with brine (5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 hexane/EtOAc) to afford the compound 12a (31.8 mg, 19%) as a yellow solid. TLC: Rf 0.28 (1:1 hexane/EtOAc). mp: 78.6-80.6 oC. 1H-NMR (400 MHz, CDCl3) delta 8.89 (AB quartet, 2H, J = 2.0 Hz), 8.08 (d, 1H, J = 8.0 Hz), 8.07 (s, 1H), 7.72 (t, 1H, J = 8.0 Hz), 7.63 (dd, 1H, J = 8.0 Hz, J = 2.0 Hz), 7.60 (d, 1H, J = 8.0 Hz), 7.12 (d, 1H, J = 8.0 Hz), 2.80 (t, 2H, J = 8.0 Hz), 2.19 (s, 3H), 1.74 (quintet , 2H, J = 8.0 Hz), 1.36 (sextet, 2H, J = 8.0 Hz), 0.88 (t, 3H, J = 8.0 Hz). 13C-NMR (100 MHz, CDCl3) delta 158.0, 149.1, 147.4, 145.6, 145.5, 142.6, 142.5, 138.9, 132.5, 132.0, 130.9, 130.2, 129.0, 123.3, 115.0, 31.6, 24.6, 23.6, 22.4, 13.7. HRMS (ESI) calcd. for C20H21N6 (M+H): 345.1822; found 345.1824.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1083 - 1086

62
[ 50998-17-9 ]
[ 1422465-02-8 ]
[ 1422465-11-9 ]

Yield	Reaction Conditions	Operation in experiment
56%	With tetrabutylammonium acetate; palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 100℃; for 22h;	To a solution of 11b (103.8 mg, 451 mumol), <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (142 mg, 679 mumol), Bu4NOAc (271 mg, 0.9 mmol) and Pd(OAc)2 (15.2 mg, 67.5 mol) in NMP (0.9 mL). The reaction mixture was stirred for 22 h at 100 oC and cooled to room temperature. The mixture was concentrated under reduced pressure, diluted with water, and extracted with EtOAc (3 × 5 mL). The EtOAc solution was washed with brine (5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 hexane/EtOAc) to afford the compound 12b (91 mg, 56%) as a pale yellow solid. TLC: Rf 0.37 (1:1 hexane/EtOAc). mp: 96.0-98.0 oC. 1H-NMR (400 MHz, CDCl3) delta 8.90 (AB quartet, 2H, J = 2.0 Hz), 8.09 (d, 1H, J = 8.8 Hz), 8.07 (d, 1H, J = 2.0 Hz) 7.72 (t, 1H, J = 8.0 Hz), 7.63 (dd, 1H, J = 8.8 Hz, J = 2.0 Hz), 7.60 (d, 1H, J = 8.0 Hz), 7.12(d, 1H, J = 8.0 Hz), 2.80 (m, 2H), 2.20 (s, 3H), 1.69-1.60 (m, 3H), 0.86 (d, 6H, J = 6.4 Hz). 13C-NMR (100 MHz, CDCl3) delta 158.2, 149.3, 147.8, 145.9, 145.8, 142.8, 142.7, 139.1, 132.6, 132.2, 131.0, 130.4, 129.2, 123.5, 115.2, 38.7, 27.8, 23.8, 23.1, 22.5. HRMS (ESI) calcd. for C21H23N6 (M+H): 359.1979; found 359.1983.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1083 - 1086

63
[ 50998-17-9 ]
[ 1422465-04-0 ]
[ 1422465-13-1 ]

Yield	Reaction Conditions	Operation in experiment
12%	With tetrabutylammonium acetate; palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 100℃; for 9h;	To a solution of 11d (30 mg, 101 mumol), <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (31.4 mg, 150 mumol), Bu4NOAc (60.2 mg, 200 mol) and Pd(OAc)2 (3.37 mg, 15 mol) in NMP (0.5 mL). The reaction mixture was stirred for 9 h at 100 oC and cooled to room temperature. The mixture was concentrated under reduced pressure, diluted with water and extracted with EtOAc (3 × 5 mL). The EtOAc solution was washed with brine (5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 hexane/EtOAc) to afford the compound 12c (5.1 mg, 12%) as a yellow solid. TLC: Rf 0.25 (1:1 hexane/EtOAc). mp: 157-159 oC. 1H-NMR (400 MHz, CDCl3) delta 8.89 (d, 1H, J = 1.6 Hz), 8.85 (d, 1H, J = 1.6 Hz), 8.13 (d, 1H, J = 8.8 Hz), 8.08 (d, 1H, J = 2.0 Hz), 7.80 (dd, 1H, J = 8.8 Hz, J = 2.0 Hz), 7.73 (t, 1H, J = 8.0 Hz), 7.63 (d, 1H, J = 8.0 Hz), 7.12 (d, 1H, J = 8.0 Hz), 6.75 (d, 1H, J = 2.0 Hz), 6.40 (t, 1H, J = 2.0 Hz) 3.64 (s, 6H), 2.18 (s, 3H). 13C-NMR (100 MHz, CDCl3) delta 161.0, 158.3, 149.0, 146.0, 145.9, 145.8, 143.0, 142.6, 139.1, 132.7, 132.4, 132.1, 131.6, 131.0, 129.5, 123.7, 115.7, 105.7, 101.1, 55.4, 23.8.HRMS (ESI) calcd. for C24H21N6O2 (M+H): 425.1721; found 425.1724.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1083 - 1086

64
[ 50998-17-9 ]
[ 1224886-20-7 ]
[ 1422465-14-2 ]

Yield	Reaction Conditions	Operation in experiment
14%	With tetrabutylammonium acetate; palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 100℃; for 23h;	To a solution of 11e (70.0 mg, 296 mumol), <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (94.1 mg, 450 mumol), Bu4NOAc (181 mg, 600 mol) and Pd(OAc)2 (10.1 mg, 45.0 mol) in NMP (0.6 mL). The reaction mixture was stirred for 23 h at 100 oC and cooled to room temperature. The mixture was concentrated under reduced pressure. Diluted with water and extracted with EtOAc (3 × 5 mL). The EtOAc solution was washed with brine (5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 hexane/EtOAc) to afford the compound 12d (15 mg, 14%) as a yellow solid. TLC: Rf 0.2 (1:1 hexane/EtOAc). mp: 208-210 oC. 1H-NMR (400 MHz, CDCl3) delta 8.89 (d, 1H, J = 1.6Hz), 8.85 (d, 1H, J = 1.6 Hz), 8.12 (d, 1H, J = 8.4 Hz), 8.07 (d, 1H, J = 1.6 Hz), 7.76 (dd, 1H, J = 8.4 Hz, J = 2.0 Hz), 7.73 (t, 1H, J = 7.6 Hz), 7.64 (d, 1H, J = 7.6 Hz), 7.59-7.57 (m, 2H), 7.30-7.27 (m, 3H), 7.12 (d, 1H, J = 7.6 Hz), 2.18 (s, 3H). 13C-NMR (100 MHz, CDCl3) delta 158.3, 149.1, 146.2, 145.9, 145.8, 143.0, 142.7, 139.1, 132.6, 132.4, 131.6, 131.0, 130.4, 129.5, 128.8, 128.4, 127.8, 123.7, 115.7, 23.8. HRMS (ESI) calcd. for C22H17N6 (M+H): 365.1509; found 365.1512.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1083 - 1086

65
[ 50998-17-9 ]
[ 1422465-05-1 ]
[ 1422465-15-3 ]

Yield	Reaction Conditions	Operation in experiment
53%	With tetrabutylammonium acetate; palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 100℃; for 17h;	To a solution of 11f (30 mg, 118 mumol), <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (37.6 mg, 180 mumol), Bu4NOAc (72 mg, 239 mumol) and Pd(OAc)2 (4.0 mg, 17.8 mumol) in NMP (0.4 mL). The reaction mixture was stirred for 17 h at 100 oC and cooled to room temperature. The mixture was concentrated under reduced pressure, diluted with water and extracted with EtOAc (3 × 5 mL). The EtOAc solution was washed with brine (5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 hexane/EtOAc) to afford the compound 12f (24 mg, 53%) as a yellow solid. TLC: Rf 0.23 (1:1 hexane/EtOAc). mp: 170171 oC. 1H-NMR (400 MHz, CDCl3) delta 8.91 (d, 1H, J = 1.6 Hz), 8.86 (d, 1H, J = 1.6 Hz), 8.13 (d, 1H, J = 8.8 Hz), 8.06 (d, 1H, J = 1.6 Hz), 7.74 (t, 1H, J = 8.0 Hz), 7.73 (d, 1H, J = 8.8 Hz), 7.64 (d, 1H, J = 8.0 Hz), 7.55 (dd, 2H, JHH = 9.2 Hz, JHF = 5.2 Hz), 7.13 (d, 1H, J = 8.0 Hz), 6.98 (dd, 2H, JHH = 9.2 Hz, JHF = 8.4 Hz), 2.18 (s, 3H). 13C-NMR (100 MHz, CDCl3) delta 162.9 (d, JCF = 247 Hz), 158.4, 149.1, 146.1, 145.9, 145.4, 143.1, 142.8, 139.2, 132.5, 132.3, 131.6, 130.9, 129.7, 129.6 (d, JCF = 8.3 Hz), 126.6, 123.8, 115.9 (d, JCF = 21.1 Hz), 115.7, 23.8. HRMS (ESI) calcd. for C22H16FN6 (M+H): 383.1415; found 383.1418.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1083 - 1086

66
[ 50998-17-9 ]
[ 1422465-06-2 ]
[ 1422465-16-4 ]

Yield	Reaction Conditions	Operation in experiment
14%	With tetrabutylammonium acetate; palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 100℃; for 32h;	To a solution of 11g (30 mg, 113 mumol), <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (36 mg, 172 mol), Bu4NOAc (66.2 mg, 220 mol) and Pd(OAc)2 (3.7 mg, 16.5 mol) in NMP (0.5 mL ). The reaction mixture was stirred for 32 h at 100 oC and cooled to room temperature. The mixture was concentrated under reduced pressure. Diluted with water and extracted with EtOAc (3 × 5 mL). The EtOAc solution was washed with brine (5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 hexane/EtOAc) to afford the compound 12g (6.1 mg, 14%) as a pale yellow solid. TLC: Rf 0.3 (1:1 hexane/EtOAc). mp: 133136 oC. 1H-NMR (400 MHz, CDCl3) delta 8.83 (d, 1H, J = 2.0 Hz), 8.80 (d, 1H, J = 2.0 Hz), 7.99 (d, 1H, J = 8.8 Hz), 7.92 (d, 1H, J = 2.0 Hz), 7.75 (t, 1H, J = 8.0 Hz), 7.65-7.62 (m, 3H), 7.33 (m, 1H), 7.17 (d, 1H, J = 8.0 Hz), 7.03 (td, 1H, J = 8.0 Hz, J = 1.2 Hz), 6.78 (d, 1H, J = 8.0 Hz), 3.27 (s, 3H), 2.27 (s, 3H). 13C-NMR (100 MHz, CDCl3) delta 158.5, 156.7, 149.4, 145.6, 145.5, 144.2, 142.7, 142.6, 139.2, 134.1, 132.1, 131.9, 131.8, 130.5, 130.1, 128.6, 123.9, 121.1, 119,6, 116.1, 111.2, 54.8, 23.9. HRMS (ESI) calcd. for C23H19N6O (M+H): 395.1615; found 395.1620.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1083 - 1086

67
[ 50998-17-9 ]
[ 1422465-07-3 ]
[ 1422465-17-5 ]

Yield	Reaction Conditions	Operation in experiment
34%	With tetrabutylammonium acetate; palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 100℃; for 13h;	To a solution of 11h (30 mg, 113 mumol), <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (34.5 mg, 165 mol), Bu4NOAc (66.2 mg, 220 mol) and Pd(OAc)2 (3.7 mg, 16.5 mol) in NMP (0.5 mL ). The reaction mixture was stirred for 13 h at 100 oC and cooled to room temperature. The mixture was concentrated under reduced pressure, diluted with water, and extracted with EtOAc (3 × 5 mL). The EtOAc solution was washed with brine (5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 hexane/EtOAc) to afford the compound 12h (15.3 mg, 34%) as a pale yellow solid. TLC: Rf 0.25 (1:1 hexane/EtOAc). mp: 195196 oC. 1H-NMR (400 MHz, CDCl3) delta 8.89 (d, 1H, J = 1.6 Hz), 8.85 (d, 1H, J = 1.6 Hz), 8.11 (d, 1H, J = 8.8 Hz), 8.07 (d, 1H, J = 1.6 Hz), 7.75 (dd, 1H, J = 8.8 Hz, J = 1.6 Hz), 7.73 (t, 1H, J = 8.0 Hz), 7.63 (d, 1H, J = 8.0 Hz), 7.51 (d, 2H, J = 8.8 Hz), 7.12 (d, 1H, J = 8.0 Hz), 6.82 (d, 2H, J = 8.8 Hz), 3.78 (s, 3H), 2.18 (s, 3H). 13C-NMR (100 MHz, CDCl3) delta 159.9, 158.3, 149.2, 146.1, 145.9, 145.8, 143.0, 142.8, 139.2, 132.7, 132.5, 131.6, 131.3, 129.6, 129.2, 123.7, 122.9, 115.7, 114.3, 55.4, 23.9. HRMS (ESI) calcd. for C23H19N6O (M+H): 395.1615; found 395.1618.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1083 - 1086

68
[ 50998-17-9 ]
[ 1422465-03-9 ]
[ 1422465-12-0 ]

Yield	Reaction Conditions	Operation in experiment
22%	With tetrabutylammonium acetate; palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 100℃; for 15h;	To a solution of 11c (50 mg, 215 mumol), <strong>[50998-17-9]<strong>[50998-17-9]6-bromoquinoxalin</strong>e</strong> (66.9 mg, 320 mumol), Bu4NOAc (129 mg, 428 mumol) and Pd(OAc)2 (7.24 mg, 32.2 mumol) in NMP (0.5 mL ). The reaction mixture was stirred for 15 h at 100 oC and cooled to room temperature. The mixture was concentrated under reduced pressure, diluted with water, and extracted with EtOAc (3 × 5 mL). The EtOAc solution was washed with brine (5 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (1:1 hexane/EtOAc) to afford the compound 12c (17 mg, 22%) as a yellow solid. TLC: Rf 0.22 (1:1 MeOH/CH2Cl2). 1H-NMR (400 MHz, CDCl3) delta 8.90 (d, 2H, J = 4.4 Hz), 8.09 (s, 1H), 8.08 (d, 1H, J = 8.0 Hz), 7.73 (t, 1H, J = 8.0 Hz), 7.63-7.60 (m, 2H), 7.13 (d, 1H, J = 8.0 Hz), 3.65 (t, 2H, J = 6.4 Hz), 2.85 (t, 2H, J = 7.6 Hz), 2.20 (s, 3H), 1.88 (quintet, 2H, J = 7.6 Hz), 1.65 (m, 2H), 1.58 (brs, 1H). 13C-NMR (100 MHz, CDCl3) delta 158.3, 149.2, 147.3, 145.8, 145.7, 142.8, 142.7, 139.1, 132.8; 132.1, 130.9, 130.4, 129.2, 123.6, 115.2, 62.4, 32.3, 25.7, 24.7, 23.8. HRMS (ESI) calcd. for C20H21N6O (M+H): 361.1771; found 361.1771.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1083 - 1086

69
[ 50998-17-9 ]
[ 6298-37-9 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2809 - 2812
[2]Organic Letters,2013,vol. 15,p. 3734 - 3737

70
[ 67-56-1 ]
[ 50998-17-9 ]
[ 6639-82-3 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3998 - 4001

71
[ 50998-17-9 ]
[ 811-98-3 ]
[ 1448366-60-6 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3998 - 4001

72
[ 50998-17-9 ]
[ 64-17-5 ]
[ 89770-34-3 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3998 - 4001

73
[ 50998-17-9 ]
[ 1020173-85-6 ]

Reference： [1]Patent: WO2013/36232,2013,A2

74
[ 50998-17-9 ]
6-bromo-1,4-dihydroquinoxalin-2,3-dione [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11096 - 11101

75
[ 50998-17-9 ]
C₁₃H₂₃NO₃*C₂HF₃O₂ [ No CAS ]
C₂₁H₂₇N₃O₃ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2013,vol. 15,p. 564 - 571

76
[ 50998-17-9 ]
C₁₁H₁₈N₂O*C₂HF₃O₂ [ No CAS ]
C₁₉H₂₂N₄O [ No CAS ]

Reference： [1]ACS Combinatorial Science,2013,vol. 15,p. 564 - 571

77
[ 50998-17-9 ]
C₁₅H₂₈N₂O₂*C₂HF₃O₂ [ No CAS ]
C₂₃H₃₂N₄O₂ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2013,vol. 15,p. 564 - 571

78
[ 50998-17-9 ]
C₁₃H₂₃NO₃*C₂HF₃O₂ [ No CAS ]
C₂₁H₂₇N₃O₃ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2013,vol. 15,p. 564 - 571

79
[ 50998-17-9 ]
C₁₁H₁₈N₂O*C₂HF₃O₂ [ No CAS ]
C₁₉H₂₂N₄O [ No CAS ]

Reference： [1]ACS Combinatorial Science,2013,vol. 15,p. 564 - 571

80
[ 50998-17-9 ]
C₁₅H₂₈N₂O₂*C₂HF₃O₂ [ No CAS ]
C₂₃H₃₂N₄O₂ [ No CAS ]

Reference： [1]ACS Combinatorial Science,2013,vol. 15,p. 564 - 571

81
[ 50998-17-9 ]
[ 1644-14-0 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 3792 - 3795

82
[ 50998-17-9 ]
[ 31954-27-5 ]
[ 1586809-55-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 12h;Inert atmosphere; Sealed tube;	General procedure: A mixture of methyl 4-bromobenzoate2a (100 mg, 0.465 mmol), methyl N-(tert-butoxycarbonyl)glycinate 3a (132 mg, 0.698 mmol), Pd2(dba)3 (8.5 mg,9.3 lmol), Xantphos (16 mg, 0.028 mmol), and cesium carbonate(303 mg, 0.930 mmol) was charged with dioxane (1.0 mL). Theresulting suspension was sparged with argon via subsurface bubblingfor 5 min, and the reaction mixture was sealed and stirredat 100 C for 12 h. The reaction was cooled to ambient temperature,diluted with EtOAc (20 mL), and filtered to remove the inorganicsalts. The filtrate was concentrated to an oil, then purified bycolumn chromatography on silica gel, eluting with an EtOAc/hexanesgradient (2-30%) to afford the desired product 4a as a colorlessgum (75% isolated yield). 1H NMR (500 MHz, DMSO-d6): d 7.90(d, J = 9.0 Hz, 2H), 7.40 (d, J = 8.5 Hz, 2H), 4.39 (s, 2H), 3.83 (s, 3H),3.68 (s, 3H), 1.37 (s, 9H). LRMS (ESI) calcd for C16H21NO6 (M+Na)+:346.1, found: 346.1.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 2646 - 2648

83
[ 50998-17-9 ]
[ 7467-91-6 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 5351 - 5358
[2]Journal of the American Chemical Society,2016,vol. 138,p. 13493 - 13496
[3]Organic Letters,2017,vol. 19,p. 3033 - 3036
[4]ChemCatChem,2019

84
[ 50998-17-9 ]
[ 180695-79-8 ]
[ 1612156-04-3 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 5771 - 5780

85
[ 50998-17-9 ]
[ 159635-49-1 ]
tert-butyl 4-(quinoxalin-6-ylmethyl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a degassed sample of tert-butyl 4-methylenepiperidine-1 -carboxylate (0.6 g, 3.04 mmol) in dry THF (10 ml.) was added 9-BBN (6.1 ml_, 3.04mmol). The resulting mixture was refluxed for 1 h. After cooling to rt, <strong>[50998-17-9]6-bromo quinoxaline</strong> (0.55 g, 2.78mmol), Pd(dppf)CI2.CH2CI2 (0.15g, 0.18 mmol), DMF (10 ml_), water (1 ml.) and K2C03 (0.6 g, 4.5mmol) were added at rt. The resulting mixture was heated at 60 C for 3 h. The reaction mixture was then cooled to rt, diluted with water (20 ml_). The pH was adjusted to 1 1 with 10% aqueous NaOH and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous Na2S04 and concentrated to get the crude product as colorless liquid. Tert-butyl 4-(quinoxalin-6-ylmethyl)piperidine-1 -carboxylate was used in the next step without further purification. Yield: 24% (0.23 g). H NMR (400 MHz, DMSO-d6): delta 8.89-8.86 (m, 2H), 8.04-8.01 (m, 3H), 2.73-2.67 (m, 2H), 2.25 (m, 9H), 1 .13 (s, 9H).

Reference： [1]Patent: WO2014/159234,2014,A1 .Location in patent: Page/Page column 103

86
[ 50998-17-9 ]
[ 14904-70-2 ]
C₈⁽¹¹⁾CH₅N₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 648 - 651

87
[ 50998-17-9 ]
[ 753-90-2 ]
C₁₀H₈F₃N₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 8460 - 8468

88
[ 50998-17-9 ]
2'-O-acetyl-3-O-descladinosyl-3-O-[2-(2'-pyridyl)acetyl]-6-O-methylerythromycin A 9-O-(2-propargyl)oxime-11,12-cyclic carbonate [ No CAS ]
3-O-descladinosyl-3-O-[2-(2'-pyridyl)acetyl]-6-O-methylerythromycin A 9-O-[3-(6'-quinoxalyl)-2-propargyl]oxime-11,12-cyclic carbonate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6437 - 6453

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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
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H370	Causes damage to organs
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H372	Causes damage to organs through prolonged or repeated exposure
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 50998-17-9 ] {[proInfo.proName]}

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[ 50998-17-9 ] Synthesis Path-Upstream 1~10

[ 50998-17-9 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 50998-17-9 ]

Bromides

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Quinoxalines

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