[ CAS No. 65896-11-9 ] {[proInfo.proName]}

Name: 65896-11-9|2-Bromo-6-fluoroaniline|98%
Brand: Ambeed
SKU: A271168
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Quality Control of [ 65896-11-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 65896-11-9 ]

Product Details of [ 65896-11-9 ]

CAS No. :	65896-11-9	MDL No. :	MFCD01310982
Formula :	C₆H₅BrFN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ALZFPYUPNVLVQM-UHFFFAOYSA-N
M.W :	190.01	Pubchem ID :	2782940
Synonyms :

Calculated chemistry of [ 65896-11-9 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	38.5
TPSA :	26.02 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) :	-6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.78
Log Po/w (XLOGP3) :	2.03
Log Po/w (WLOGP) :	2.6
Log Po/w (MLOGP) :	2.67
Log Po/w (SILICOS-IT) :	2.25
Consensus Log Po/w :	2.27

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.79
Solubility :	0.308 mg/ml ; 0.00162 mol/l
Class :	Soluble
Log S (Ali) :	-2.2
Solubility :	1.19 mg/ml ; 0.00625 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.17
Solubility :	0.128 mg/ml ; 0.000673 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.28

Safety of [ 65896-11-9 ]

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 [ 65896-11-9 ]

* 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 [ 65896-11-9 ]
Downstream synthetic route of [ 65896-11-9 ]

[ 65896-11-9 ] Synthesis Path-Upstream 1~9

1
[ 348-54-9 ]
[ 367-24-8 ]
[ 141474-37-5 ]
[ 65896-11-9 ]

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2870 - 2873

2
[ 348-54-9 ]
[ 367-24-8 ]
[ 65896-11-9 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 13, p. 2083 - 2085

3
[ 2252-37-1 ]
[ 65896-11-9 ]

Reference： [1] Organic Letters, 2009, vol. 11, # 5, p. 1051 - 1054

4
[ 348-54-9 ]
[ 367-24-8 ]
[ 141474-37-5 ]
[ 65896-11-9 ]

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2870 - 2873

5
[ 348-54-9 ]
[ 367-24-8 ]
[ 65896-11-9 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 13, p. 2083 - 2085

6
[ 348-54-9 ]
[ 65896-11-9 ]

Reference： [1] Chinese Journal of Chemistry, 2018, vol. 36, # 9, p. 815 - 818

7
[ 65896-11-9 ]
[ 450412-29-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2008, vol. 47, # 5, p. 888 - 890

8
[ 65896-11-9 ]
[ 886762-70-5 ]

Reference： [1] Organic Letters, 2009, vol. 11, # 5, p. 1051 - 1054
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 6, p. 1858 - 1860
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 8, p. 2609 - 2613

9
[ 7632-04-4 ]
[ 65896-11-9 ]
[ 886762-70-5 ]

Reference： [1] Patent: US2007/15744, 2007, A1, . Location in patent: Page/Page column 64-65

[ 65896-11-9 ] Synthesis Path-Downstream 1~88

1
[ 107-83-5 ]
[ 65896-11-9 ]
[ 690664-20-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 1A Methyl (2E)-3-[2-amino-3-fluorophenyl]propenoate Starting with 42.00 g (221.04 mmol) of <strong>[65896-11-9]2-bromo-6-fluoroaniline</strong>, the general procedure [A] gives 29.66 g (68% of theory) of product. HPLC (method 1): Rt=4.14 min MS (ESI-pos): m/z=196 (M+H)+

Reference： [1]Patent: US2007/281953,2007,A1

2
6,6-dimethyl-3-[4-(4-methyl-piperazin-1-yl)-benzoylamino]-5,6-dihydro-4H-pyrrolo [3,4-c]pyrazole-2-carboxylic acid ethyl ester dihydrochloride [ No CAS ]
[ 65896-11-9 ]
N-(2-bromo-6-fluorophenyl)-6,6-dimethyl-3-([4-(4-methylpiperazin-1-yl)phenyl]carbonyl}amino)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxamide trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		By working in an analogous manner the following compounds were prepared:

Reference： [1]Patent: WO2008/43745,2008,A1 .Location in patent: Page/Page column 63; 64

3
[ 947159-63-9 ]
[ 65896-11-9 ]
C₁₄H₁₀ClBrFN₃O₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3864 - 3867

4
[ 358-23-6 ]
[ 65896-11-9 ]
[ 845830-28-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; at 70℃; for 3h;	This solution was treated with 1. ON HC1 to PH=L and extracted with CH2C12 (2X40ML). The combined organic extracts were washed with 1. ON HCl (20ML), dried over MGS04, filtered and concentrated in vacuo to provide the bis mesylated product. This material was dissolved in methanol (20ml) and treated with 1. ON NAOH (LOML) for 45 minutes. After this time, this solution was acidified with 1. ON HCl (12ml) and partitioned between CH2C12 (50 + 25ml) and brine (10ML). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. This residue was purified by column chromatography eluting with a 0-100% ETOAC/CH2C12 gradient to give N- (2-bromo-6-fluorophenyl)- methanesulfonamide. 1H NMR (400MHZ, CDC13) 8 7.41-7. 47 (M, 1H), 7. 16 (d, 1H, J=12. 5HZ), 7.14- 7.17 (M, 1H), 6.22 (br s, 1H) and 3.27 (s, 3H) ppm.

Reference： [1]Patent: WO2005/16886,2005,A1 .Location in patent: Page/Page column 41

5
[ 845830-20-8 ]
[ 65896-11-9 ]
[ 845830-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In 1,4-dioxane; at 90℃; for 0.25h;	EXAMPLE 22 N- [(1R)-1-(3,3'-difluoro-2'-[(trifluoromethyl)sulfonyl]amino}-1,1'-bipnyl-4-yl)ethyl]-1-[(trifluoro- acetyl) amino] cyclopropanecarboxamide N- { (LR)-L- [2-FLUORO-4- (4, 4,5, 5-TETRAMETHYL-1, 3, 2-DIOXABOROLAN-2-YL) phenyl] ethyl}-1- [(trifluoroacetyl) amino] cyclopropanecarboxamide (1.50g, 3. 377MMOL), 2-bromo-6-flouroaniline (401ul, 3.545mmol), tris (dibenzylideneacetone) dipalladium (309mg, 0. 338MMOL), cesium carbonate (l. lOg, 3.377mmol) and 1.65M tri-t-butylphosphine in dioxane (491ul, 0. 810MMOL) were suspended in dioxane (15ml), degassed with Argon purge and heated to 90C for 15 minutes. After this time, the mixture was filtered through a Gelman Acrodisc and the filter was washed with EtOAc (10ml) and methanol (20ML). The combined filtrates were concentrated in vacuo and the residue purified by column chromatography eluting with a 0-100% ETAOC/CH2C12 gradient to give N-[(LR)-1-(2 -AMINO-3, 3 -DIFLUORO-1, 1 -BIPHENYL- 4-yl) ETHYL]-1-[(TRIFLUOROACETYL) AMINO] cyclopropanecarboxamide. Low resolution mass spectrometry: (M+H+) = 428.2. 1H NMR (400MHZ, (CD3) 2SO) 8 9.79 (s, 1H), 8.28 (d, 1H, J=7.6Hz), 7.48 (t, 1H, J=8.2Hz), 7.19-7. 26 (M, 2H), 7.02-7. 09 (M, 1H), 6.89 (d, 1H, J=7.6Hz), 6.61-6. 68 (M, 1H), 5.22-5. 29 (M, 1H), 1.45-1. 57 (M, 2H), 1.42 (d, 3H, J=7. 1HZ) and 0.93-1. 08 (M, 2H) ppm.

Reference： [1]Patent: WO2005/16886,2005,A1 .Location in patent: Page/Page column 47

6
[ 292638-85-8 ]
[ 65896-11-9 ]
[ 690664-20-1 ]

Reference： [1]Patent: WO2005/47278,2005,A2 .Location in patent: Page/Page column 19
[2]Patent: WO2004/96778,2004,A1 .Location in patent: Page/Page column 22
[3]Patent: WO2004/41790,2004,A1 .Location in patent: Page/Page column 25
[4]Patent: WO2004/99212,2004,A1 .Location in patent: Page/Page column 15; 23-24
[5]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103

7
[ 3282-30-2 ]
[ 65896-11-9 ]
[ 865626-99-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With pyridine; at 20℃; for 3h;	<strong>[65896-11-9]2-Bromo-6-fluoroaniline</strong> (8.2 g, 43.2 mmol) was dissolved in pyridine (10 mL) and treated with pivaloyl chloride (7.0 mL, 57.2 mmol). The reaction was stirred at room temperature for 3 h. The reaction mixture was concentrated in vacuo and treated with ethyl acetate (50 mL). Mixture was washed 1 N hydrochloric acid (2×), then brine. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was triturated with hexanes to give a solid which was filtered, washed with hexanes, and dried in vacuo. The title compound was obtained as white solid in 76% yield. 1H NMR (300 MHz, CDCl3): delta 7.39-7.31 (m, 1H), 7.14-7.03 (m, 2H), 6.98 (bs, 1H), 1.34 (s, 9H). Mass spec.: 274.1 (MH)+, 276.1 (MNa)+.
76%	With pyridine; In methanol; at 20℃; for 3h;	N-(2-Bromo-6-fluorophenyl)pivalamide. <strong>[65896-11-9]2-Bromo-6-fluoroaniline</strong> (43.2 mmol, 8.2 g) was dissolved in pyridine (124 mmol, 10 mL). Pivaloyl chloride (57.15 mmol, 7.0 mL) was added to the mixture. Reaction was stirred at room temperature for 3 hours. Reaction mixture was concentrated in vacuo. Residue was treated with ethyl acetate (50 mL). Mixture was washed 2×1N HCl, 1× brine. Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Residue was treated with hexanes and triturated. Resulting solids were filtered off, washed with hexanes then dried in vacuo. Title compound was obtained as white solid in 76% yield. 1H NMR (300 MHz, CDCl3): delta=7.39-7.31 (m, 1H), 7.14-7.03 (m, 2H), 6.98 (bs, 1H), 1.34 (s, 9H). MS m/e (M+H)+=274.1, 276.1.

Reference： [1]Patent: US2005/215576,2005,A1 .Location in patent: Page/Page column 48-49
[2]Patent: US2007/49577,2007,A1 .Location in patent: Page/Page column 9-10
[3]Angewandte Chemie - International Edition,2014,vol. 53,p. 4945 - 4949

8
[ 65896-11-9 ]
[ 375853-82-0 ]
C₁₆H₂₁FN₂O₂ [ No CAS ]

Reference： [1]Patent: WO2006/3494,2006,A2 .Location in patent: Page/Page column 144

9
[ 884048-29-7 ]
[ 65896-11-9 ]
[ 884034-53-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With isopropylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 90℃; for 0.5h;	Example 97:; v To a DMF solution (6.3mL) of <strong>[65896-11-9]6-fluoro-2-bromoaniline</strong> (247mg, 1.3mmol) was added the alkyne 92a (350mg, 1.19mmol), Pd(PPh3)2CI2 (33mg, 0.047mmol), CuI (17.8mg, 0.09mmol) and i- Pr2NH (2.1 mL). The mixture was degassed in vacuo, flushed with nitrogen and heated at 90C for 30min. The resulted solution was concentrated in vacuo. The residue was purified with silica gel column chromatography (15% EtOAc in hexanes) giving the title compound (300mg, 62% yield) as a solid. 1H NMR (CDCI3): delta 9.18 (1 H, s), 8.37 (1 H, s), 7.95-7.86 (4H, m), 7.56 (2H, m), 7.23 (1 H, d, J=7.6Hz), 7.00 (1H, d, J=7.8Hz), 6.97-6.90 (1 H, m), 6.59-6.52 (1H, m), 5.12 (1H, m), 4.39-4.30 (4H, m), 3.27 (1 H, dd, J=7.2, 4.8Hz), 1.31 (3H, t, J=7.1 Hz). LCMS (APCI positive): 405 (M+H+).

Reference： [1]Patent: WO2006/40646,2006,A1 .Location in patent: Page/Page column 65

Yield	Reaction Conditions	Operation in experiment
		Reaction with concentrated ammonia yields the corresponding sulfonamide, m.p. 162-165 C., which is brominated and then desulfonylated with concentrated acid to yield the 2-bromo-6-fluoroaniline and at the same time saponified.

11
[ 16588-75-3 ]
[ 65896-11-9 ]
[ 917389-23-2 ]

Reference： [1]Patent: WO2006/133822,2006,A1 .Location in patent: Page/Page column 24-25; 25

12
[ 7632-04-4 ]
[ 65896-11-9 ]
[ 886762-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	In water; acetic acid; at 55℃; for 4h;	To a suspension of sodium perborate tetrahydrate (135.374 g., 886.4 mmol) in 500 mL acetic acid at 55 C. was added dropwise a solution of <strong>[65896-11-9]2-bromo-6-fluoro-phenylamine</strong> (33.685 g., 177.271 mmol) in 70 mL acetic acid over 1 hour. The reaction mixture was stirred at 55 C. for an additional 3 hours, then cooled to 0 C. in an ice bath. Insoluble materials were removed by filtration through a plug of celite, which was rinsed with 100 mL acetic acid. The combined acetic acid fractions were added to 3 L ice water with stirring to give a waxy solid which was removed by filtration. The crude solid was dissolved in 250 mL ethyl acetate, washed three times with 200 mL of 10% aqueous hydrogen chloride, 200 mL saturated sodium bicarbonate and 100 mL brine. The solution was concentrated in vacuo to give 11.51 g of 1-bromo-3-fluoro-2-nitro-benzene as a red oil, 1H NMR (CDCl3, 300 MHz) delta: 7.26 (m, 1H), 7.38 (m, 1H), 7.49 (m, 1H)

Reference： [1]Patent: US2007/15744,2007,A1 .Location in patent: Page/Page column 64-65

13
[ 65896-11-9 ]
[ 690664-20-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 2A Methyl (2E)-3-[2-amino-3-fluorophenyl]propenoate Starting with 42.00 g (221.04 mmol) of <strong>[65896-11-9]2-bromo-6-fluoroaniline</strong>, the general procedure [B] gives 29.66 g (68% of theory) of product. HPLC (method 1): Rt=4.14 min MS (ESIpos): m/z=196 (M+H)+

Reference： [1]Patent: US2007/185121,2007,A1

14
[ 5259-65-4 ]
[ 65896-11-9 ]
8-fluoro-4a-methyl-4,4a,9,9a-tetrahydro-1H-carbazol-2(3H)-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 177 - 180

15
[ 65896-11-9 ]
[ 450412-29-0 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 888 - 890

16
[ 1146950-56-2 ]
[ 65896-11-9 ]
[ 1146950-55-1 ]

Yield	Reaction Conditions	Operation in experiment
	trimethylaluminum; In toluene;	EXAMPLE 6 3-(4-Fluoro-1,3-benzoxazol-2-yl)-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyridin-2-amine 2M Trimethylaluminium in toluene (0.75 ml) was added to a solution of <strong>[65896-11-9]2-bromo-6-fluoro-aniline</strong> (0.229 g) in toluene (30 ml). The mixture was stirred for 30 minutes, then methyl 2-amino-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyridine-3-carboxylate (0.19 g) was added. The mixture was heated to 120 C. for 18 hours, allowed to cool and then quenched with 10% aqueous Rochelle's salt solution. The organic fraction was purified by SCX ion-exchange chromatography to give crude 2-amino-N-(2-bromo-6-fluorophenyl)-5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridine-3-carboxamide; Mass Spectrum: M+H+ 472.1; RT 0.87 min.

Reference： [1]Patent: US2009/118305,2009,A1

17
[ 2252-37-1 ]
[ 65896-11-9 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 1051 - 1054

18
[ 65896-11-9 ]
[ 886762-70-5 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 1051 - 1054
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1858 - 1860
[3]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2609 - 2613

19
[ 24850-33-7 ]
[ 65896-11-9 ]
[ 1170692-57-5 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 1911 - 1913
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 16032 - 16036
Angew. Chem.,2017,vol. 129,p. 16248 - 16252,5

20
[ 864775-58-6 ]
[ 55552-70-0 ]
[ 65896-11-9 ]
[ 1208324-68-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 673 - 678

21
[ 14160-68-0 ]
[ 65896-11-9 ]
[ 1242272-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; at 145℃;Inert atmosphere;	To the ketal of Step 1 (8.46 kg, 24.31 mol), were charged <strong>[65896-11-9]2-bromo-6-fluoroaniline</strong> (2.509 L, 22.10 mol) and acetic acid (0.253 L, 4.42 raol) under nitrogen. The mixture was heated to 145 0C and ethanol was removed by distillation. The product was used in the next reaction.

Reference： [1]Patent: WO2010/99039,2010,A1 .Location in patent: Page/Page column 29

22
C₁₃H₂₁NO₆ [ No CAS ]
[ 65896-11-9 ]
[ 1240382-33-5 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 3574 - 3577

23
[ 65896-11-9 ]
(2-bromo-6-fluorophenyl)hydrazine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		<strong>[65896-11-9]2-Bromo-6-fluoroaniline</strong> (2.0 g, 10 mmol) was dissolved in hydrochloric acid (7.0 niL, 12 N aqueous, 8.0 eq?iv) and cooled to 0 0C. An aqueous solution (10 mL) of sodium nitrite (0.80 g, 11 mmol, 1.1 equiv) was added dropwise over 30 minutes via addition funnel and the mixture was stirred for an additional 30 minutes at 0 0C. A hydrochloric acid solution (10 mL, 12 N aqueous) of stannous chloride (7.1 g, 31 mmol, 3.0 equiv) was then added to the mixture over 45 minutes via addition funnel and the mixture was stirred for an additional 1 hour at 0 0C. To the mixture, sodium hydroxide (30 mL, 1 N aqueous) was added slowly until basic (p? >; 8). The mixture was warmed to ambient temperature, poured into sodium hydroxide (50 mL, 25% aqueous) and the aqueous layer was extracted with diethyl ether (3 X 250 mL). The combined organic extracts were dried with sodium sulfate, filtered and partially concentrated in vacuo. The mixture was diluted with diethyl ether (200 mL) and treated with gaseous hydrochloric acid until saturated, resulting in a white precipitate, which was filtered and washed with diethyl ether (2 X 50 mL), providing the titled compound as a white solid.

Reference： [1]Patent: WO2010/96338,2010,A1 .Location in patent: Page/Page column 39

24
C₂₆H₂₉ClN₂O₅ [ No CAS ]
[ 65896-11-9 ]
[ 1252646-54-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 2h;	To a solution of 2-(l-(((9Eta-fluoren-9-yl)methoxy)carbonyl)-4-(ter£- butoxycarbonyl)piperazin-2-yl)acetic acid (5 g, 10.72 mmol) in dichloromethane (100 mL) with Lambda/,Lambda/-dimethylformamide (2 drops) was added oxalyl dichloride (3.4 g, 26.8 mmol). The reaction mixture was stirred at room temperature for 1 hour, then concentrated. Tetrahydrofuran (100 mL) was added to the concentrate followed by the slow addition of a solution containing 2-bromo-6-fluoroanaline (3 g, 16 mmol) and diisopropylethylamine (9 mL) in tetrahydrofuran (20 mL). The solution was stirred at room temperature for 2 hours before the addition of piperazine (2.77 g, 32.2 mmol) after which the solution was stirred for 15 hours. The reaction mixture was concentrated onto silica gel and purified via flash chromatography (0-100 % ethyl acetate/hexane, then 0-10 % methanol/dichloromethane) to afford the title compound. 1H NMR (300 MHz, DMSO-J6) delta ppm 7.47 - 7.65 (m, 1 H) 7.21 - 7.46 (m, 2 H) 3.55 - 4.05 (m, 2 H) 2.67 - 3.14 (m, 3 H) 2.49 - 2.67 (m, 2 H) 2.26 - 2.46 (m, 2 H) 1.39 (s, 9 H); MS (APCI+) m/z 418.2 (M+H)+.

Reference： [1]Patent: WO2010/124042,2010,A2 .Location in patent: Page/Page column 118-119

25
[ 60041-31-8 ]
[ 65896-11-9 ]
[ 1286756-88-4 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 2326 - 2329

26
[ 108-94-1 ]
[ 65896-11-9 ]
C₁₂H₁₃BrFN [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7438 - 7441

27
[ 65896-11-9 ]
[ 1333385-79-7 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7438 - 7441

28
[ 65896-11-9 ]
[ 1333385-92-4 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7438 - 7441

29
[ 65896-11-9 ]
[ 1333386-09-6 ]
(-)-(4aR,9aS)-methyl 8-fluoro-trans-2,3,4,4a-tetrahydro-1H-carbazole-9-(9aH)-carboxylate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7438 - 7441

30
[ 5720-06-9 ]
[ 65896-11-9 ]
[ 1338379-58-0 ]

Yield	Reaction Conditions	Operation in experiment
62%	With palladium diacetate; 2-dicyclohexylphosphino-2',6'-dimethylbiphenyl; In toluene; at 100℃; for 3h;	A well-dried 200 mL three-neck eggplant flask(Condenser, with three-way cock, with magnetic stir bar)2-Methoxyphenylboronic acid3.19 g (21 mmol), 2.80 g of <strong>[65896-11-9]2-bromo-6-fluoroaniline</strong> (manufactured by Tokyo Chemical Industry Co., Ltd.)(20 mmol), 0.022 g of palladium acetate(0.1 mmol) 2-Dicyclohexylphosphino-2 ', 6'-dimethylbiphenyl0.082 g (0.2 mmol),13.8 g (60 mmol) of potassium phosphate monohydrate was added,The mixture was suspended in 40 mL of toluene and reacted at 100 C. for 3 hours.After adding 100 mL of water to this reaction solution and extracting with toluene,The organic layer is dried over MgSO4The solvent was distilled off under reduced pressure to obtain a crude product.Crude product is silica gel column chromatograph(Eluent: hexane / ethyl acetate = 93/7)Compound 4 by purifying with2.71 g (62%, light yellow liquid) was obtained.

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 12438 - 12441
[2]Patent: JP5769444,2015,B2 .Location in patent: Paragraph 0167-0169

31
[ 65896-11-9 ]
[ 1392223-22-1 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 12438 - 12441

32
[ 65896-11-9 ]
[ 1392223-23-2 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 12438 - 12441

33
[ 65896-11-9 ]
[ 1392223-24-3 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 12438 - 12441

34
[ 65896-11-9 ]
[ 1392223-21-0 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 12438 - 12441

35
[ 201230-82-2 ]
[ 108-24-7 ]
[ 65896-11-9 ]
[ 1044749-59-8 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 12599 - 12602

36
[ 65896-11-9 ]
[ 1431300-98-9 ]

Reference： [1]Patent: WO2013/56679,2013,A1

37
[ 65896-11-9 ]
[ 1431300-73-0 ]

Reference： [1]Patent: WO2013/56679,2013,A1

38
[ 65896-11-9 ]
[ 1431299-94-3 ]

Reference： [1]Patent: WO2013/56679,2013,A1

39
[ 65896-11-9 ]
[ 1985-12-2 ]
[ 1431300-97-8 ]

Yield	Reaction Conditions	Operation in experiment
45.2%		Preparation of intermediate 3A:N-(4-bromophenyl)-4-fluorobenzothiazol-2-ylamine<strong>[65896-11-9]2-Bromo-6-fluoroaniline</strong> (500 mg, 2.63 mmol) and potassium carbonate (5726 mg, 5.26 mmol) were placed in a flask, to which was added 10 mL of DMSO. l-Bromo-4-thiocyanato-benzene (845 mg, 3.95 mmol) was added under nitrogen protection and resulting mixture was stirred at room temperature for 30 min. Cuprous iodide (50 mg, 0.263 mmol) was added and then heated to 120 C under nitrogen protection, and reacted overnight. The mixture was cooled to room temperature, poured into water to give a precipitate, which was filtered to give 383 mg of compound 3 A, which was used directly in the next step without further purification. Yield: 45.2%.MS (ESI, m/z): [M+H]+: 324.0

Reference： [1]Patent: WO2013/56679,2013,A1 .Location in patent: Page/Page column 34

40
[ 22363-16-2 ]
[ 65896-11-9 ]
[ 1474030-52-8 ]

Reference： [1]MedChemComm,2013,vol. 4,p. 1202 - 1207

41
[ 201230-82-2 ]
[ 62-53-3 ]
[ 65896-11-9 ]
[ 149-73-5 ]
[ 1593583-16-4 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 1420 - 1424
Angew. Chem.,2014,vol. 126,p. 1444 - 1448,5

42
[ 65896-11-9 ]
[ 1627168-07-3 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 4945 - 4949

43
[ 65896-11-9 ]
[ 1629909-28-9 ]

Reference： [1]Chinese Journal of Chemistry,2014,vol. 32,p. 592 - 598

44
[ 65896-11-9 ]
[ 1629909-39-2 ]

Reference： [1]Chinese Journal of Chemistry,2014,vol. 32,p. 592 - 598

45
[ 65896-11-9 ]
C₆H₃BrFN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butylnitrite; trimethylsilylazide; In acetonitrile; at 0 - 20℃; for 2h;	General procedure: Different aniline (0.75 mmol) was dissolved in CH3CN (10 mL) in a 25-mL round-bottomed flask and cooled to 0C in an ice bath. To this stirred mixture was added t-BuONO (1.125 mmol) followed by TMSN3 (0.9 mmol) dropwise. The resulting solution was stirred at room temperature for 2 h. Compound 2 (0.5 mmol), CuI(0.1 mmol) and Et3N (0.6 mmol) were then added and the reaction was stirred at room temperature. The progress of the reaction was monitored by TLC. After the completion of reaction, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate as eluting solution to afford the target compounds 3 [25-29]. The data of 3a-3w are shown as follows. We selected one compound, 3d, as a representative compound and signal positions of carbon protons were assigned.

Reference： [1]Chinese Journal of Chemistry,2014,vol. 32,p. 592 - 598
[2]Research on Chemical Intermediates,2016,vol. 42,p. 5495 - 5508

46
[ 937-14-4 ]
[ 65896-11-9 ]
[ 288-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; aniline; In hexane; dichloromethane; dimethyl sulfoxide;	Preparation 43 4-Bromobenzo[c][1,2,5]oxadiazole <strong>[65896-11-9]2-Bromo-6-fluoroaniline</strong> (7.3 g, 38.4 mmol) was dissolved in dichloromethane (180 mL), cooled to 0-5 C. and treated with a solution of the 3-chlorobenzoperoxoic acid (18.94 g, 77 mmol) in dichloromethane (200 mL) over ca 90 min. After completion of the addition, the reaction mixture was allowed to warm up and stir for 2 h. The reaction mixture was diluted with additional dichloromethane and agitated with 2% Na2SO3 solution, saturated NaHCO3, dried, and evaporated. The solid residue was slurried with hexane (200 mL) and collected by filtration, washed with hexane and sucked dry to give 4.4 g of the nitroso compound as a white solid. The GC-MS looks like the starting aniline (m/z=190/193) but the aniline is a liquid. The crude nitroso compound was stirred in dry DMSO (50 mL) to produce a pale green slurry. Sodium azide (2.498 g, 38.4 mmol) was added in portions over 30 min with cooling applied to keep the temperature less than 30 C. GCMS showed formation of the oxadiazole (m/z=198/200). The mixture was stirred overnight, partitioned between ethyl acetate and water to produce a clear organic phase and a nearly clear aqueous phase.

Reference： [1]Patent: US2014/274702,2014,A1 .Location in patent: Page/Page column

47
[ 65896-11-9 ]
C₁₉H₁₆F₄N₂O₄ [ No CAS ]

Reference： [1]Patent: WO2015/88931,2015,A1

48
[ 65896-11-9 ]
C₁₉H₁₄F₄N₂O₃ [ No CAS ]

Reference： [1]Patent: WO2015/88931,2015,A1

49
[ 65896-11-9 ]
C₃₀H₃₀F₄N₄O₄*C₇H₆O₃ [ No CAS ]

Reference： [1]Patent: WO2015/88931,2015,A1

50
[ 65896-11-9 ]
[ 917389-30-1 ]

Reference： [1]Patent: WO2015/88931,2015,A1
[2]Patent: WO2006/133822,2006,A1

51
[ 65896-11-9 ]
[ 917389-32-3 ]

Reference： [1]Patent: WO2015/88931,2015,A1
[2]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103
[3]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103
[4]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103
[5]Angewandte Chemie - International Edition,2017,vol. 56,p. 16032 - 16036
Angew. Chem.,2017,vol. 129,p. 16248 - 16252,5
[6]Patent: WO2006/133822,2006,A1
[7]Patent: WO2006/133822,2006,A1

52
[ 292638-85-8 ]
[ 65896-11-9 ]
C₁₀H₁₀FNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With N-Methyldicyclohexylamine; chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)] palladium(II); In Isopropyl acetate; at 80℃; for 5h;Inert atmosphere;	To a degassed solution of <strong>[65896-11-9]2-bromo-6-fluoroaniline</strong> (1, 99.5 g, 0.524 mol), methyl acrylate (95.0 mL, 1.05 mol), Chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)] palladium(II) (0.537 g, 1.05 mmol) in isopropyl acetate (796 mL), was added degassed N,N- dicyclohexylmethylamine (135 mL, 0.628 mol). The resulting reaction was heated to 80 C and allowed to stir at this temperature for 5 hours. The resulting slurry was cooled to 20 C and filtered. The filtrate was washed with 1 M citric acid to provide a solution that contained compound 2 (99.3 g, 97% assay yield) in isopropyl acrylate, which was used without further purification. 'H NMR (500 MHz, d-CHCl3): deltaEta 7.79 ppm (1H, d, J= 15.9 Hz), 7.17 ppm (1H, d, J= 8.2 Hz), 7.00 ppm (1H, ddd, J= 10.7, 8.2, 1.2 Hz), 6.69 ppm (1H, td, J = 8.2, 5.1 Hz), 6.38 ppm (1H, d, J= 15.9 Hz), 4.06 ppm (2H, br s), 3.81 ppm (3H, s).

Reference： [1]Patent: WO2015/88931,2015,A1 .Location in patent: Page/Page column 17

53
[ 1885-14-9 ]
[ 65896-11-9 ]
C₁₇H₁₄FNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With disodium hydrogenphosphate; In Isopropyl acetate; at 30 - 60℃;	To a solution of compound 2 (48.8 g, 0.250 mol) in 683 mL of isopropyl acetate was added 244 mL of water, followed by di-sodium hydrogen phosphate (53.2 g, 0.375 mol). To the resulting solution was added phenyl chloroformate (39.2 mL, 0.313 mol) dropwise over 30 minutes. The resulting reaction was heated to 30 C and allowed to stir at this temperature for 5 hours for 4 hours and then was heated to 60 C and allowed to stir at this temperature for 5 hours for an additional 2 hours to remove excess phenyl chloroformate. An additional 293 mL of isopropyl acetate was then added and the reaction mixture was allowed to stir at room temperature until the solids completely dissolved into solution. The resulting reaction mixture was transferred to a separatory funnel and the organic phase was washed with 98 mL of water and collected to provide a solution of compound 3 in isopropyl acetate, which was used without further purification. 1H NMR (500 MHz, d-acetonitrile): deltaEta 7.91 ppm (1H, d, J= 15.9 Hz), 7.85 ppm (1H, br s), 7.63 ppm (1H, d, J= 7.9 Hz), 7.45-7.39 ppm (3H, m), 7.33-7.27 ppm (2H, m), 7.21 ppm (2H, br), 6.60 ppm (1H, d, J= 16.0 Hz).

Reference： [1]Patent: WO2015/88931,2015,A1 .Location in patent: Page/Page column 18

54
[ 76-05-1 ]
[ 65896-11-9 ]
N-(2-bromo-6-hydroxyphenyl)-2,2,2-trifluoroacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With Oxone; In 1,4-dioxane; at 90℃;Schlenk technique; Inert atmosphere;	General procedure: A Schlenk tube was charged with Oxone (0.398 g, 0.648mmol) and trifloroacetic acid (0.099 mL, 1.296 mmol) in anhydrous dioxane (2 mL) under argon. To this mixture was added 2-fluoroaniline (0.06 g, 0.54 mmol), and the reaction mixture was heated to 90 C under argon until starting material was consumed. As the reaction progressed, the color turned from lightred to dark red. The mixture was then cooled to room temperature and washed with a saturated aqueous sodium bicarbonate.The mixture was extracted with EtOAc (2 × 20 mL) and the combined organic layers were dried over Na2SO4. After filtering andremoval of the solvent under reduced pressure in vacuo, theresidue was purified by silica gel (100-200 mesh) column chromatography(hexane-EtOAc, 9:1), to afford a pale-brown solid(65%) of 2-hydroxy-N-trifluoroacetanilides from 2-fluoroaniline(2a).

Reference： [1]Synlett,2015,vol. 26,p. 1258 - 1262

55
4-(5,6,7,8-tetrahydroisoquinolin-3-yl)but-3-yn-1-ol [ No CAS ]
[ 65896-11-9 ]
C₁₉H₁₉FN₂O [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 2194 - 2200

56
[ 65896-11-9 ]
C₁₈H₁₁Br₂ClFN₇O [ No CAS ]

Reference： [1]Research on Chemical Intermediates,2016,vol. 42,p. 5495 - 5508

57
[ 32315-10-9 ]
[ 64982-62-3 ]
[ 65896-11-9 ]
(1S)-N-(2-bromo-6-fluorophenyl)-1-methyl-3,4-dihydroisoquinoline-2(1H)-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		General procedure: D.7. Synthesis of com ounds 126 to 131. 126 to 131 To a solution of anilines (0.12 mmol) in THF (800 mu) at 0 C, was added triphosgene (21 mg, 0.07 mmol). The mixture is stirred at rt for 1 h30, then TEA (70 mu, 0.50 mmol), (1 S)-1-methyl-1 ,2,3,4-tetrahydroisoquinoline hydrobromide (commercial, 27 mg, 0.12 mmol). The mixture was stirred at rt for 1 h, then overnight at 60 C. The reaction mixture is diluted with EtOAc (2 mL), then washed with an aqueous saturated solution of NaHC03. The organic layer was dried over MgS04, filtered and concentrated under vacuum. The residue was purified by reverse phase chromatography (basic mode, LCMS prep). compounds 126, 127, 128, 129, 130 and 131 were synthesized following this method. (1 S)-N-(2-bromo-6-fluorophenyl)-1-methyl-3,4-dihvdroisoguinoline-2(1 H)-carboxamide 126. Compound 126 was prepared using <strong>[65896-11-9]2-bromo-6-fluoroaniline</strong> as starting material Yield: 52%. LCMS (ES+): 363 (M+H)+, 96.9% purity.

Reference： [1]Patent: WO2016/55479,2016,A1 .Location in patent: Page/Page column 187-188

58
[ 882670-66-8 ]
[ 32315-10-9 ]
[ 65896-11-9 ]
3-(2-bromo-6-fluorophenyl)-1-[2-(²H₃)methoxy-5-(trifluoromethyl)phenyl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.8 g	With triethylamine; In dichloromethane; at 0 - 25℃; for 3h;Inert atmosphere;	[00196] To a solution of triphosgene (1.25 g, 0.35 equiv) in dichloromethane (55.0 mL) was added TEA (14.5 mL 10.00 equiv) dropwise with stirring at 0 0 C. Then a solution of 2- bromo-6-fiuoroaniline (1, 2.0 g, 10.53 mmol, 1.00 equiv) in dichloromethane (10 mL) was added dropwise with stirring at 0 C. The reaction was allowed to warm to room-temperature and a solution of 2-(2H3)-methoxy-5-(trifluoromethyl)aniline (Intermediate 3, 2.04 g, 10.51 mmol, 1.00 equiv) in dichloromethane (20 mL) was added dropwise with stirring. The resulting solution was stirred for 3 h at 25 C with an inert atmosphere of nitrogen. The reaction progress was monitored by LCMS. The resulting mixture was concentrated under vacuum and the residue was dissolved in 20 mL of ethyl acetate, washed with 10 mL of sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 2.8 g of 3-(2-bromo-6-fluorophenyl)-l-[2-(2H3)methoxy-5- (trifluoromethyl)phenyl]urea (2) as a white solid. LC-MS: m/z = 410.05 [M+l]+ NMR (300 MHz, DMSO-de) delta: 8.91-8.81 (m, 2 H), 8.50-8.49 (m, 1 H), 7.56-7.20 (m, 5 H) .

Reference： [1]Patent: WO2016/109360,2016,A1 .Location in patent: Paragraph 00196

59
[ 65896-11-9 ]
[ 917389-21-0 ]

Reference： [1]Patent: WO2016/109360,2016,A1
[2]Patent: WO2006/133822,2006,A1

60
[ 65896-11-9 ]
methyl 2-[2-chloro-8-fluoro-3-[2-methoxy-5-(trifluoromethyl)phenyl]-3,4-dihydroquinazolin-4-yl]acetate [ No CAS ]

Reference： [1]Patent: WO2016/109360,2016,A1
[2]Patent: WO2006/133822,2006,A1

61
[ 65896-11-9 ]
[ 791117-40-3 ]

Reference： [1]Patent: WO2016/109360,2016,A1
[2]Patent: WO2006/133822,2006,A1

62
[ 65896-11-9 ]
[ 917389-37-8 ]
[ 917389-32-3 ]

Reference： [1]Patent: WO2016/109360,2016,A1
[2]Patent: WO2006/133822,2006,A1

63
[ 65896-11-9 ]
methyl 2-[8-fluoro-3-[2-methoxy-5-(trifluoromethyl)phenyl]-2-[4-(3-(²H₃)methoxyphenyl)piperazin-1-yl]-3,4-dihydroquinazolin-4-yl]acetate [ No CAS ]

Reference： [1]Patent: WO2016/109360,2016,A1

64
[ 65896-11-9 ]
(S)-2-(8-fluoro-3-(2-methoxy-5-(trifluoromethyl)phenyl)-2-(4-(3-(<SUP>2</SUP>H₃)methoxyphenyl)piperazin-1-yl)-3,4-dihydroquinazolin-4-yl)acetic acid [ No CAS ]
(R)-2-(8-fluoro-3-(2-methoxy-5-(trifluoromethyl)phenyl)-2-(4-(3-(<SUP>2</SUP>H₃)methoxyphenyl)piperazin-1-yl)-3,4-dihydroquinazolin-4-yl)acetic acid [ No CAS ]

Reference： [1]Patent: WO2016/109360,2016,A1

65
[ 65896-11-9 ]
(2-((2,5-dichloropyrimidin-4-yl)amino)-3-fluorophenyl)dimethylphosphine oxide [ No CAS ]

Reference： [1]Patent: CN105330698,2016,A

66
[ 7211-39-4 ]
[ 65896-11-9 ]
(2-amino-3-fluorophenyl)dimethylphosphine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.16%	With palladium on activated charcoal; potassium carbonate; In water; at 15 - 160℃; for 3h;Microwave irradiation;	At 15 deg.C, <strong>[65896-11-9]2-bromo-6-fluoroaniline</strong> (1.00 g, 5.26 mmol) and dimethylphosphine oxide (451.84 mg, 5.79 mmol) in water (20ml) mixture was added potassium carbonate ( 2.91 g, 21.05 mmol) and Pd / C (150 mg). The reaction mixture was stirred at 160 deg.C microwave heating for 3 hours. TLC (petroleum ether: ethyl acetate = 10: 1) showed the reaction was complete. The reaction mixture (20mL × 4) and extracted with dichloromethane. The combined organic layer was filtered, the filtrate was concentrated and purified by column chromatography (dichloromethane: methanol = 1: 0-10: 1) afforded the title compound (100mg, yield 10.16%) as a yellow solid.

Reference： [1]Patent: CN105330698,2016,A .Location in patent: Paragraph 0660; 0661; 0662; 0663

67
[ 1885-14-9 ]
[ 65896-11-9 ]
1-(3-methoxyphenyl)piperazine dihydrochloride [ No CAS ]
C₁₈H₁₉BrFN₃O₂ [ No CAS ]

Reference： [1]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103

68
[ 65896-11-9 ]
C₃₀H₂₉BrF₄N₄O₄ [ No CAS ]

Reference： [1]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103

69
[ 65896-11-9 ]
methyl-(2E)-3-(3-fluoro-2-((((2-methoxy-5-(trifluoromethyl)phenyl)amino)(4-(3-methoxyphenyl)-piperazin-1-yl)methylene)amino)phenyl)acrylate 2-hydrobenzoate [ No CAS ]

Reference： [1]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103

70
[ 65896-11-9 ]
methyl (2E)-3-(3-fluoro-2-((((2-methoxy-5-(trifluoromethyl)phenyl)imino)methylene)amino)phenyl)acrylate [ No CAS ]

Reference： [1]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103

71
[ 65896-11-9 ]
methyl (S)-2-(8-fluoro-3-(2-methoxy-5-(trifluoromethyl)phenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-4-yl)acetate [ No CAS ]

Reference： [1]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 16032 - 16036
Angew. Chem.,2017,vol. 129,p. 16248 - 16252,5

72
[ 65896-11-9 ]
[ 917389-26-5 ]

Reference： [1]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103

73
[ 65896-11-9 ]
(S)-methyl 2-(8-fluoro-3-(2-methoxy-5-(trifluoromethyl)phenyl)-2-(4-(3-methoxyphenyl)piperazin-1-yl)-3,4-dihydroquinazolin-4-yl)acetate (2S,3S)-2,3-bis((4-methylbenzoyl)oxy)succinate ethyl acetate [ No CAS ]

74
[ 65896-11-9 ]
C₁₈H₁₈BrClFN₃O [ No CAS ]

Reference： [1]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103

75
[ 65896-11-9 ]
[ 917389-34-5 ]

Reference： [1]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103
[2]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103
[3]Patent: WO2006/133822,2006,A1

76
[ 65896-11-9 ]
(S)-methyl 2-(8-fluoro-3-(2-methoxy-5-(trifluoromethyl)phenyl)-2-(4-(3-methoxyphenyl)piperazin-1-yl)-3,4-dihydroquinazolin-4-yl)acetate [ No CAS ]

Reference： [1]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103
[2]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103
[3]Organic Process Research and Development,2016,vol. 20,p. 1097 - 1103
[4]Angewandte Chemie - International Edition,2017,vol. 56,p. 16032 - 16036
Angew. Chem.,2017,vol. 129,p. 16248 - 16252,5
[5]Patent: WO2006/133822,2006,A1
[6]Patent: WO2006/133822,2006,A1
[7]Patent: WO2006/133822,2006,A1
[8]Patent: WO2006/133822,2006,A1

77
[ 65896-11-9 ]
2-ethyl-4-bromo-6-fluoroaniline [ No CAS ]