[ CAS No. 2770-11-8 ] {[proInfo.proName]}

Name: 2770-11-8|2-(4-Chlorophenoxy)aniline|98%
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SKU: A281845
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Quality Control of [ 2770-11-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2770-11-8 ]

Product Details of [ 2770-11-8 ]

CAS No. :	2770-11-8	MDL No. :	MFCD00025168
Formula :	C₁₂H₁₀ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QKKBREBZMUFUDS-UHFFFAOYSA-N
M.W :	219.67	Pubchem ID :	76010
Synonyms :

Calculated chemistry of [ 2770-11-8 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	62.37
TPSA :	35.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.45 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.49
Log Po/w (XLOGP3) :	3.09
Log Po/w (WLOGP) :	3.72
Log Po/w (MLOGP) :	3.22
Log Po/w (SILICOS-IT) :	2.94
Consensus Log Po/w :	3.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.61
Solubility :	0.0541 mg/ml ; 0.000246 mol/l
Class :	Soluble
Log S (Ali) :	-3.5
Solubility :	0.0698 mg/ml ; 0.000318 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.92
Solubility :	0.00265 mg/ml ; 0.0000121 mol/l
Class :	Moderately soluble

Medicinal Chemistry

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

Safety of [ 2770-11-8 ]

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 [ 2770-11-8 ]

* 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 [ 2770-11-8 ]
Downstream synthetic route of [ 2770-11-8 ]

[ 2770-11-8 ] Synthesis Path-Upstream 1~6

1
[ 39145-47-6 ]
[ 2770-11-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: With iron; ammonium chloride In ethanol; water for 1 h; Heating / reflux	2-(4-Chlorophenoxy)phenyIamine (AMR01029) C₁₂H₁₀ClNO, MW 219.67Previously described: Wardrop, A. W. H.; Gordon, L. S.; Harrison, J. M.; Inch, T. D. J. Chem. Soc, Perkin I1976, 1276-1285 Commercially availableTo a refluxing mixture of iron powder (3.18 g, 57.28 mmol) and ammonium chloride (383 mg, 7.15 mmol) in ethanol (45 mL) and water (8 mL) was added l-(2,4- dichlorophenoxy)-2-nitrobenzene (AMR01028, 2.2 g, 8.81 mmol) and the resulting mixture was stirred at reflux for 1 h. After removal of the solvent, the residue was diluted in aqueous sodium hydrogen carbonate (40 mL) and extracted with DCM (3 x 20 mL). The organic layer was dried (MgSO₄), filtered and evaporated to give AMR01029 (1.50 g, 78percent) as a colorless oil which was used in the next step without further purification. Rf: 0.53 (DCM) ¹H NMR (270 MHz, CDCl₃) .pound.3.77 (2H, br s, NH₂), 6.71 (IH, m), 6.83 (2H, m), 6.89 (2H₅ AA'BB'), 6.99 (IH, m) and 7.25 (2H, AA'BB').

Reference： [1] Patent: WO2007/3934, 2007, A2, . Location in patent: Page/Page column 119
[2] Journal of the American Chemical Society, 2014, vol. 136, # 40, p. 14060 - 14067
[3] Journal of the Chemical Society, 1931, p. 529,533
[4] Journal of the Chemical Society, 1925, vol. 127, p. 2011
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1976, p. 1279 - 1285
[6] Collection of Czechoslovak Chemical Communications, 2000, vol. 65, # 6, p. 862 - 880
[7] Patent: WO2007/3934, 2007, A2, . Location in patent: Page/Page column 145-146
[8] European Journal of Medicinal Chemistry, 2016, vol. 120, p. 244 - 251
[9] Organic Letters, 2017, vol. 19, # 14, p. 3855 - 3858
[10] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 9, p. 322
[11] Organic and Biomolecular Chemistry, 2018, vol. 16, # 42, p. 7861 - 7870

2
[ 106-48-9 ]
[ 2770-11-8 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 2000, vol. 65, # 6, p. 862 - 880
[2] Journal of the Chemical Society, 1925, vol. 127, p. 2011
[3] Journal of the American Chemical Society, 2014, vol. 136, # 40, p. 14060 - 14067
[4] European Journal of Medicinal Chemistry, 2016, vol. 120, p. 244 - 251
[5] Organic Letters, 2017, vol. 19, # 14, p. 3855 - 3858
[6] Organic and Biomolecular Chemistry, 2018, vol. 16, # 42, p. 7861 - 7870

3
[ 88-73-3 ]
[ 2770-11-8 ]

Reference： [1] Journal of the Chemical Society, 1931, p. 529,533
[2] Journal of the Chemical Society, 1925, vol. 127, p. 2011
[3] European Journal of Medicinal Chemistry, 2016, vol. 120, p. 244 - 251
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 42, p. 7861 - 7870

4
[ 1493-27-2 ]
[ 2770-11-8 ]

Reference： [1] Journal of the American Chemical Society, 2014, vol. 136, # 40, p. 14060 - 14067
[2] Organic Letters, 2017, vol. 19, # 14, p. 3855 - 3858

5
[ 2216-12-8 ]
[ 2770-11-8 ]

Reference： [1] Journal of the Chemical Society, 1931, p. 529,533

6
[ 1121-74-0 ]
[ 2770-11-8 ]

Reference： [1] Journal of the Chemical Society, 1931, p. 529,533

[ 2770-11-8 ] Synthesis Path-Downstream 1~88

1
[ 2770-11-8 ]
[ 51230-49-0 ]

Reference： [1]Journal of the Chemical Society,1931,p. 529,533

2
[ 2770-11-8 ]
(2-chloro-phenyl)-(2-iodo-phenyl)-ether [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1940,vol. 62,p. 3144

3
[ 358-23-6 ]
[ 2770-11-8 ]
[ 47226-91-5 ]

Reference： [1]Patent: DE2118190,1972,
Chem.Abstr.,1972,vol. 77

4
[ 2770-11-8 ]
[ 555-16-8 ]
[ 68-11-1 ]
[ 56885-15-5 ]

Reference： [1]Zeitschrift fur Chemie,1975,vol. 15,p. 268 - 270

5
[ 2770-11-8 ]
[ 1147550-11-5 ]
[ 98-88-4 ]
[ 76838-13-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 4409 - 4421

6
[ 2770-11-8 ]
[ 104-12-1 ]
[ 16172-05-7 ]

Reference： [1]Journal of medicinal chemistry,1968,vol. 11,p. 163 - 164

7
[ 2770-11-8 ]
[ 103-71-9 ]
[ 16172-04-6 ]

Reference： [1]Journal of medicinal chemistry,1968,vol. 11,p. 163 - 164

8
[ 2770-11-8 ]
N-[2-(4-chloro-phenoxy)-phenyl]-N-(2-methoxy-benzyl)-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 423 - 438

9
[ 106-48-9 ]
[ 2770-11-8 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,2000,vol. 65,p. 862 - 880
[2]Journal of the Chemical Society,1925,vol. 127,p. 2011
[3]Journal of the American Chemical Society,2014,vol. 136,p. 14060 - 14067
[4]European Journal of Medicinal Chemistry,2016,vol. 120,p. 244 - 251
[5]Organic Letters,2017,vol. 19,p. 3855 - 3858
[6]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7861 - 7870
[7]European Journal of Medicinal Chemistry,2019,vol. 171,p. 195 - 208

10
[ 88-73-3 ]
potassium-salt of salicylaldehyde [ No CAS ]
[ 2770-11-8 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,2000,vol. 65,p. 862 - 880

11
[ 2770-11-8 ]
1-(4-Chloro-phenyl)-1H-benzo[1,3,4]oxadiazine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Chemical Research - Part S,1995,p. 276 - 277

12
[ 2770-11-8 ]
[ 39504-66-0 ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 12143 - 12158

13
[ 2770-11-8 ]
[ 21418-34-8 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 4409 - 4421

14
[ 2770-11-8 ]
[ 76840-87-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 4409 - 4421

15
[ 2216-12-8 ]
[ 2770-11-8 ]

Reference： [1]Journal of the Chemical Society,1931,p. 529,533

16
[ 2770-11-8 ]
2-(4-chloro-phenoxy)-4-nitro-aniline [ No CAS ]

Reference： [1]Journal of the Chemical Society,1931,p. 529,533

17
[ 2770-11-8 ]
[ 873977-72-1 ]

Reference： [1]Journal of the Chemical Society,1931,p. 529,533

18
[ 2770-11-8 ]
acetic acid-[2-(4-chloro-2-nitro-phenoxy)-4-nitro-anilide] [ No CAS ]

Reference： [1]Journal of the Chemical Society,1931,p. 529,533

19
[ 1121-74-0 ]
[ 2770-11-8 ]

Reference： [1]Journal of the Chemical Society,1931,p. 529,533

20
[ 88-73-3 ]
[ 2770-11-8 ]

Reference： [1]Journal of the Chemical Society,1931,p. 529,533
[2]Journal of the Chemical Society,1925,vol. 127,p. 2011
[3]European Journal of Medicinal Chemistry,2016,vol. 120,p. 244 - 251
[4]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7861 - 7870

21
[ 2770-11-8 ]
[ 54763-82-5 ]

Reference： [1]Indian Journal of Chemistry,1974,vol. 12,p. 258 - 262

22
[ 2770-11-8 ]
[2-(2-chloro-dibenzo[b,f][1,4]oxazepin-11-ylsulfanyl)-ethyl]-dimethyl-amine [ No CAS ]

Reference： [1]Indian Journal of Chemistry,1974,vol. 12,p. 258 - 262

23
[ 2770-11-8 ]
[ 54841-34-8 ]

Reference： [1]Indian Journal of Chemistry,1974,vol. 12,p. 258 - 262

24
[ 2770-11-8 ]
[ 2058-52-8 ]

Reference： [1]Indian Journal of Chemistry,1974,vol. 12,p. 258 - 262

25
[ 2770-11-8 ]
[ 30690-45-0 ]

Reference： [1]Indian Journal of Chemistry,1974,vol. 12,p. 258 - 262

26
[ 865486-28-8 ]
[ 2770-11-8 ]
C₁₉H₁₄ClF₃N₂O₂ [ No CAS ]

Reference： [1]Patent: US6365620,2002,B2 .Location in patent: Page column 10

27
C₈H₇ClF₃NO [ No CAS ]
[ 2770-11-8 ]
C₂₀H₁₆ClF₃N₂O₂ [ No CAS ]

Reference： [1]Patent: US6365620,2002,B2 .Location in patent: Page column 10

28
C₈H₇ClF₃NO [ No CAS ]
[ 2770-11-8 ]
C₂₀H₁₆ClF₃N₂O₂ [ No CAS ]

Reference： [1]Patent: US6365620,2002,B2 .Location in patent: Page column 10

29
C₈H₇ClF₃NO₂ [ No CAS ]
[ 2770-11-8 ]
C₂₀H₁₆ClF₃N₂O₃ [ No CAS ]

Reference： [1]Patent: US6365620,2002,B2 .Location in patent: Page column 10

30
C₇H₂ClF₃N₂O [ No CAS ]
[ 2770-11-8 ]
C₁₉H₁₁ClF₃N₃O₂ [ No CAS ]

Reference： [1]Patent: US6365620,2002,B2 .Location in patent: Page column 10

31
C₈H₅ClF₃NO₂ [ No CAS ]
[ 2770-11-8 ]
C₂₀H₁₄ClF₃N₂O₃ [ No CAS ]

Reference： [1]Patent: US6365620,2002,B2 .Location in patent: Page column 10

32
[ 56515-89-0 ]
[ 2770-11-8 ]
4-[2-(4-chlorophenoxy)-phenylamino]-azepane-1-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%		Preparation of 4-[2-(4-chlorophenoxy)-phenylamino]-azepane-l-carboxyIic acid ethylester STX 1703 C21H25ClN2O3, MW: 388.90To a solution of 2-(4-chlorophenoxy)phenylamine (121 mg, 0.55 mmol), ethyl-4- oxazepane-1-carboxylate (205 mg, 1.1 mmol) and acetic acid (165 mg, 2.75 mmol) in DCE (1.8 ml) was added sodium triacetoxyborohydride (291 mg, 1.38 mmol). This solution was then heated at 1000C for 25 minutes in a CEM discover microwave (fixed hold time set to on). The reaction mixture was then quenched with saturated aqueous sodium bicarbonate solution (5 ml) and extraction with ethyl acetate (3 x 5 ml) followed. The combined organics were concentrated in vacuo and purification by flash chromatography proceeded (eluant: 8:2 hexane: ethyl acetate) to provide the title compound as a transparent oil (60.7 mg, 28%). 1H NMR (270 MHz, CDCl3): delta 1.24 (3H, t, J = 6.9 Hz, CH3), 1.43-2.10 (6H, m, 6 x CH), 3.41-3.54 (5H, m, 5 x CH)5 3.98-4.28 (3H, m, NH, CH2), 6.59-6.67 (2H, m, Ar-H), 6.78-6.82 (IH, dd, J= 1.5, 7.9 Hz, Ar-H), EPO <DP n="170"/>6.86-6.89 (2H, m, Ar-H), 7.00-7.08 (IH5 m, Ar-H), 7.21-7.24 ppm (2H, m, Ar-H). 1 U3C/ NMR (67.93 MHz, CDC13): delta 14.7, 14.9, 15.6, 21.4, 24.6, 24.9, 25.0, 33.1, 34.2, 34.8, 35.1, 42.9, 43.1, 46.2, 46.4, 52.6, 52.8, 61.1, 61.3, 112.1, 118.6, 118.7, 120.0, 124.5, 129.7, 130.1, 137.8, 139.1, 142.9, 143.6, 145.3, 155.1, 156.2, 156.4, 168.4, 170.4 ppm LCMS: M+U: 389.42 HPLC: 97.79% (3.062 min, isocratic 90% acetonitrile, 10% water at 1 ml/min).

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 167-168

33
[ 40638-98-0 ]
[ 2770-11-8 ]
N-[2-(4-chlorophenoxy)phenyl]-3-acetamido-3-phenylpropanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 14h;	Preparation of N-[2-(4-chlorophenoxy)phenyl]-3-acetamido-3-phenylpropanamide STX1858 C23H21ClN2O3, MW: 408.88 EPO <DP n="177"/>To a pre-stirred solution of iV-acetyl-3-phenyl-beta-alanine (104 mg, 0.50 mmol), EDC (265 mg, 1.38 mmol), triethylamine (70 mg, 0.69 mmol) and DMAP (6 mg, 0.046 mmol) in anhydrous DCM (25 ml), was added 2-(4-chlorophenoxy)phenylamine (100 mg, 0.46 mmol). This mixture was then allowed to stir at room temperature for 14 h. The reaction mixture was washed with 2.5M NaOH (20 ml), 2M HCl (20 ml) and the organics were then dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (eluant; DCM to 9:1 DCM:MeOH) then proceeded to afford the desired product as an off-white solid (58.9 mg, 31%). 1H NMR (270 MHz, CDCl3): delta 2.03 (3H, s, CH3), 2.83-2.99 (2H, m, CH2), 5.30-5.40 (IH, m, CH), 6.73-6.77 (IH, dd, J= 1.5, 8.2 Hz, Ar-H), 6.83-6.86 (2H, m, Ar-H), 6.95-7.03 (IH, td, J= 1.7, 7.9 Hz, Ar-H), 7.05-7.11 (IH, td, J= 1.7, 7.9 Hz, Ar-H), 7.19-7.30 (7H, m, Ar-H), 7.60 (IH, br s, Ar-H), 8.22-8.25 ppm (IH, dd, J - 1.5, 8.0 Hz, Ar-H). LCMS: M+H: 409.44 HPLC: 98.66% (2.268 mins, isocratic 90% acetonitrile, 10% water at 1 rnl/min).

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 174-175

34
[ 2770-11-8 ]
[ 179898-00-1 ]
1-BOC-4-[2-(4-chloro-phenoxy)-phenylamino]-3,4-dihydro-2H-quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%		l-BOC-4-[2-(4-Chloro-phenoxy)-phenylamino]-3,4-dihydro-2H-quinoline (CMS02032, STX 2168)C26H27ClN2O3, MoI. Wt: 450.96 EPO <DP n="239"/>To a mixture of l-BOC-2,3-dihydro-lH-quinolin-4-one (0.190 g, 0.77 mmol) and 2~(4- chlorophenoxy)-aniline (0.35 g, 1.6 mmol, 2.1 eq.) in toluene (10 mL) was added chlorotriisopropoxytitanium(IV) (0.4 mL, 2.1 eq.) and the resulting deep orange solution stirred at room temperature overnight. Saturated NaHCO3 solution (10 mL) was added and the phases separated. The organic layer was separated dried over anhydrous magnesium sulphate then filtered and evaporated. The residue was re-dissolved in TEDF (25 mL) and cooled to 0 0C under nitrogen. A solution of succinic acid (0.189 g, 1.6 mmol) in THF (5 mL) was added followed by IM borane tetrahydrofuran complex (1.6 mL, 2.1eq.). The reaction was allowed to warm to room temperature before the addition of saturated NaHCO3 solution (100 mL). The volatile solvent was removed under reduced pressure then ethyl acetate (100 mL) was added and the layers separated. The organic layer was dried, evaporated and then purified by column chromatography (flashmasterlL 50 g column) using 0-30% ethyl acetate/hexanes as eluent to give the desired product (0.223 g, 72%) as a colourless foam which showed;1H NMR (270 MHz, CDCl3) delta 1.46 (9H, s, 3 x CH3), 1.90-2.05 (IH, m), 2.05-2.20 (IH, m), 3.44-3.55 (IH, m), 3.91-4.03 (IH, m), 4.37 (IH, br s, NH), 4.50-4.59 (IH, m), 6.65 (IH, dt, J = 7.9 and 1.2 Hz), 6.80-6.90 (4H, m), 6.95-7.10 (2H, m), 7.20-7.35 (4H, m) and 7.70 (IH, d, J = 7.9 Hz);13C NMR (67.9 MHz, CDCl3) 328.43 (CH3), 29.94 and 41.36 (both CH2), 49.26 (CH), 111.90 and 117.26 (both Ar-CH), 118.82 (2 x Ar-CH), 119.57, 123.61, 123.89, 125.37, 127.49 and 127.92 (all Ar-CH) and 129.71 (2 x Ar-CH);

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 236-237

35
[ 2770-11-8 ]
4-[2-(4-chlorophenoxy)phenylcarbamoyl]piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%		4-[2-(4-Chlorophenoxy)phenylcarbamoyI]piperidine-l-carboxylic acid fer/-butyl ester (AMR01031) C23H27ClN2O4, MW 430,92A solution of piperidine-l,4-dicarboxylic acid mono-tert-butyl ester (AMRO 1030, 417 mg, 1.82 mmol) in dry DCM (8 mL) was stirred under nitrogen, and 4- dimethylaminopyridine (DMPA, 40 mg, 0.327 mmol), (l-(3-dimemylaminopropyl)-3- ethylcarbodiimide hydrochloride (EDC, 1.05 g, 5.46 mmol) and triethylamine (0.25 mL) were added. The resulting mixture was stirred for 30 min under nitrogen and 2-(4-chloro- phenoxy)-phenylamine (AMR01029, 400 mg, 1.82 mmol) in dry DCM (4 mL) was added. After stirring at room temperature for 24 h, the mixture was diluted with DCM, washed EPO <DP n="123"/>with HCl IM (3 x 25 mL), water, saturated NaHCO3 (2 x 25 mL) and brine. The organic layer was dried (MgSO4), filtered and evaporated. Flash chromatography on silica gel of the crude product using hexane/EtOAc 8:2 as eluent gave starting material (104 mg). Further elution using hexane/EtOAc 7:3 gave 4-[2-(4-chlorophenoxy)- phenylcarbamoyl]piperidine-l-carboxylic acid tert-butyl ester (430 mg, 55%) as a white solid, mp 97-99 0C. Rf: 0.22 (hexane/EtOAc 7:3) LC/MS (APCI) tr = 3.83 min, m/z 431.23 (33), 429.21 (M'-H,100). 1H NMR (270 MHz, CDCl3) £ 1.44 (9H5 s, 3CH3), 1.68 (2H, m, CH2), 1.83 (2H, m, CH2), 2.36 (IH, tt, J= 11.4, 3.7 Hz), 2.75 (4 H, br t, 2CH2), 4.11 (4H, m, 2CH2), 6.81 (IH, dd, J= 8.2, 1.5 Hz, ArH), 6.93 (2H, AA'BB', ArH), 7.01 (IH, td, ArH), 7.12 (IH, td, ArH), 7.31 (2H, AA'BB', ArH), 7.68 (IH, br s, NH) and 8.40 (IH, dd, J= 6.9, 1.5 Hz, ArH).

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 120-121

36
[ 32161-06-1 ]
[ 2770-11-8 ]
1-{4-[2-(4-chlorophenoxy)phenylamino]-piperidin-1-yl}-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%		Preparation of l-{4-[2-(4-chlorophe?oxy)phenylamino]-piperidin-l-yl}-ethanoneSTX1629 Cj9H21ClN2O2, MW: 344.8572To a solution of 2-(4-chlorophenoxy)phenylamine (200 mg, 0.91 mmol), l-acetyl-4- piperidone (277 mg, 1.96 mmol) and acetic acid (294 mg, 4.9 mmol) in DCE (3 ml) was added sodium triacetoxyborohydride (519 mg, 2.45 mmol). This solution was then heated at 1000C for 15 minutes in a CEM discover microwave (fixed hold time set to on). The reaction mixture was then quenched with saturated aqueous sodium bicarbonate solution (10 ml) and extraction with ethyl acetate (3 x 10 ml) followed. The combined organics were concentrated in vacuo and purification by flash chromatography proceeded (eluant: 8:2 hexane: ethyl acetate) to provide the title compound as a transparent oil (263.5 mg, EPO <DP n="157"/>84%). Analytical data as previously reported. HPLC: 98.13% (2.747 min; isocratic, 90% acetonitrile: 10% water at 1 ml/min).

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 154-155

37
[ 2770-11-8 ]
[ 13139-14-5 ]
tert-butyl 1-[2-(4-chlorophenoxy)phenylcarbamoyl]-2-(1H-indol-3-yl)ethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 96h;	Preparation of f°rt-butyl-l-[2-(4-chlorophenoxy)phenylcarbomoyl]-2-(lH-indol-3- yl)ethylcarbamate STX1857 C21H28ClN3O4, MW: 505.99 EPO <DP n="176"/>To a pre-stirred solution of JV-(alpha)-BOC-Z-tryptophan (152 mg, 0.50 mmol), EDC (265 mg, 1.38 mmol), triethylamine (70 mg, 0.69 mmol) and DMAP (6 mg, 0.046 mmol) in anhydrous DCM (25 ml), was added 2-(4-cHorophenoxy)phenylamine (100 mg, 0.46 mmol). This mixture was then allowed to stir at room temperature for 4 days. The reaction mixture was washed with 2.5M NaOH (20 ml), 2M HCl (20 ml) and the organics were then dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (eluant; DCM to 9:1 DCM:MeOH) then proceeded to afford the desired product as an off-white solid (109 mg, 470Zo)-1H NMR (270 MHz, CDCl3): delta 1.35 (9H, br s, (CHj)3), 3.22-3.45 (2H, m, CH2), 4.59 (IH, br s, CH), 5.14 (IH, br s, NH), 6.67-6.90 (2H, m, Ar-H), 7.00-7.25 (9H, m, Ar-H), 7.64 (IH, d, J = 7.9 Hz, Ar-H), 7.95 (IH, s, NH), 8.11 (IH5 s, NH), 8.42-8.45 ppm (IH, d, J= 7.7 Hz, Ar-H). LCMS: M+H: 506.33 HPLC: 99.73% (3.848 mins, isocratic 90% acetonitrile, 10% water at 1 ml/min).

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 173-174

38
[ 64142-63-8 ]
[ 2770-11-8 ]
1-acetyl-{4-[2-(4-chloro-phenoxy)phenyl]amino}-3,4-dihydro-2H-quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		l-Acetyl-{4-[2-(4-Chloro-phenoxy)-phenyIamino]-3,4-dihydro-2H-quinoline (CMS02020, STX2138).C23H21ClN2O2, MoI. Wt: 392.88 EPO <DP n="237"/>To a mixture of l-Acetyl-2,3-dihydro-lH-quinolin-4-one (0.155 g, 0.82 mmol) and 2-(4- chlorophenoxy)-aniline (0.35 g, 1.6 mmol, 2 eq.) in toluene (10 mL) was added chlorotriisopropoxytitanium(IV) (0.4 mL, 2 eq.) and the resulting deep orange solution stirred at room temperature overnight. Saturated NaHCO3 solution (10 mL) was added and the phases separated. The organic layer was separated dried over anhydrous magnesium sulphate then filtered and evaporated. The residue was re-dissolved in THF (25 mL) and cooled to 0 0C under nitrogen. A solution of succinic acid (0.189 g, 1.6 mmol) in THF (5 mL) was added followed by IM borane tetrahydrofuran complex (1.6 mL, 2.eq.). The reaction was allowed to warm to room temperature before the addition of saturated NaHCOs solution (100 mL). The volatile solvent was removed under reduced pressure then ethyl acetate (100 mL) was added and the layers separated. The organic layer was dried, evaporated and then purified by column chromatography (fiashmasterIL 5O g column) using 0-30% ethyl acetate/hexanes as eluent to give the desired product (0.246 g, 76%) as a pale yellow foam which showed;1H NMR (270 MHz, CD3OD) delta 1.80-2.00 (IH, m, 3-CH), 2.24 (3H, s, CH3), 2.20-2.35 (IH, m, 3-CH), 3.40-3.55 (IH, m, 2-CH), 4.05-4.25 (IH, m, 3-CH), 4.30-4.40 (IH, m, NH), 4.40-4.50 (IH, m, 4-CH), 6.69 (IH, dt, J = 7.4 and 1.5 Hz), 6.77 (IH, dd, J = 8.2 and 1.5 Hz), 6.83-6.94 (4H, m), 7.01-7.17 (2H, m) and 7.21-7.30 (6H, m); 13C NMR (67.9 MHz, CDCl3) £ 23.22 (CH3), 31.24 (CH2), 49.26 (CH), 60.39 (CH2), 122.25, 117.65 and 118.69 (all Ar-CH), 118.80 (2 x Ar-CH), 119.56, 124.61, 125.40, 125.54 and 127.59 (all Ar-CH), 127.90 (C), 129.79 (2 x Ar-CH), 138.16, 139.11, 142.92, 156.06, and 170.08 (all C); LRMS (AP+) m/z 391.56 ( (M-H)+, 100%); LC/MS (AP+) tr = 1.41 min ( >99 %), m/z 391.56 (M-H) +; HPLC tr = 6.79 min (100 %).

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 234-235

39
[ 2770-11-8 ]
[ 86996-26-1 ]
1-{4-[2-(4-chlorophenoxy)phenylamino]-piperidin-1-yl}-2-methylpropan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%		Preparation of 1- {4- [2-(4-chIorophenoxy)phenylamino] -piperidin-1 -yl}-2- methylpropan-1-one STX1701 C21H25ClN2O2, MW: 372.8939To a solution of 2-(4-chlorophenoxy)phenylamine (100 mg3 0.45 mmol), l-isobutyryl-4- piperidone (144 mg, 0.735 mmol) and acetic acid (147 mg, 2.45 mmol) in DCE (1.5 ml) was added sodium triacetoxyborohydride (260 mg, 1.23 mmol). This solution was then heated at 1000C for 15 minutes in a CEM discover microwave (fixed hold time set to on).The reaction mixture was then quenched with saturated aqueous sodium bicarbonate solution (5 ml) and extraction with ethyl acetate (3 x 5 ml) followed. The combined organics were concentrated in vacuo and purification by flash chromatography proceeded(eluant: 8:2 hexane: ethyl acetate) to provide the title compound as a transparent oil (44 mg, 26%). 1HNMR (270 MHz, CDCl3): delta 1.10 (6H, d, J= 6.7 Hz, CH(CH3)2), 1.25-1.35(2H, m, 2 x CH), 2.03-2.27 (2H, m, 2 x CH), 2.76-2.85 (2H, m, 2 x CH)3 3.18 (IH, t, J=11.4 Hz, CH), 3.48-3.60 (IH, m, CH), 3.83-3.88 (IH, bd, J = 13.9 Hz3 CH)3 3.97-4.12 (IH, m, NH), 4.41-4.46 (IH, bd, J= 13.9 Hz, CH), 6.61-6.67 (IH, td, J- 1.2, 0.7, 7.7 Hz3 EPO <DP n="164"/>ArH)5 6.74-6.77 (IH, dd, J= 1.2, 8.2 Hz, ArH), 6.79-6.82 (IH3 dd, J= 1.5, 7.9 Hz, ArH), 6.85-6.90 (2H, m, ArH), 7.01-7.07 (IH, td, J= 1.2, 0.8, 7.2 Hz, ArH), 7.20-7.25 ppm (2H, m, ArH). LCMS: M+R: 373.49 HPLC: 93.75% (2.692 min, isocratic 90% acetonitrile, 10% water at 1 ml/min).

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 161-162

40
[ 919118-54-0 ]
[ 2770-11-8 ]
{4-[2-(4-chlorophenoxy)phenylamino]-piperidin-1-yl}-cyclopentylmethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%		Preparation of {4-[2-(4-chlorophenoxy)phenylamino]-piperidin-l-yl}- cyclopentylmethanone STX1685 C23H27ClN2O2, MW: 398.94To a solution of 2-(4-cUorophenoxy)phenylarnine (100 mg, 0.45 mmol), 1- cyclopentylcarbonyl-4-piperidone (144 mg, 0.735 mmol) and acetic acid (147 mg, 2.45 mmol) in DCE (1.5 ml) was added sodium triacetoxyborohydride (260 mg, 1.23 mmol). This solution was then heated at 100C for 15 minutes hi a CEM discover microwave (fixed hold time set to on). The reaction mixture was then quenched with saturated aqueous sodium bicarbonate solution (5 ml) and extraction with ethyl acetate (3 x 5 ml) EPO <DP n="162"/>followed. The combined organics were concentrated in vacuo and purification by flash chromatography proceeded (eluant: 8:2 hexane: ethyl acetate) to provide the title compound as a transparent oil (82 mg, 43%). 1H NMR (300 MHz, CDCl3): delta 1.16-1.36 (2H, m, 2 x CH)3 1.47-1.56 (2H, m, 2 x CH), 1.59-1.78 (6H, m, 6 x CH)5 1.93-2.08 (2H, m, 2 x CH), 2.76-2.87 (2H, m, 2 x CH), 3.07-3.18 (IH, m, CH), 3.43-3.52 (IH, sept, J = 3.9 Hz, CH), 3.78-3.89 (IH, bd, J = 13.8 Hz, CH), 3.97-4.10 (IH, m, CH), 4.31-4.42 (IH, bd, J = 13.5 Hz, NH), 6.55-6.62 (IH, td, J = 1.5, 1.2, 1.2, 7.7 Hz, ArH), 6.68-6.71 (IH, dd, J = 1.5, 8.1 Hz, ArH), 6.73-6.77 (IH, dd, J = 1.5, 8.1 Hz, ArH), 6.79-6.84 (2H, m, ArH), 6.95-7.01 (IH, td, J = 1.5, 0.6, 1.5, 7.7 Hz, ArH), 7.16-7.22 ppm (2H, m, ArH). 13C NMR (67.93 MHz, CDC13): delta 19.5, 19.6, 30.2, 32.2, 33.2, 40.6, 44.1, 49.9, 112.2, 117.2, 118.8, 119.6, 125.3, 127.9, 129.8, 138.9, 143.1, 156.1, 175.4 ppm LCMS: M+H: 421.46 HPLC: 98.41% (3.124 rnin, isocratic 90% acetonitrile, 10% water at 1 rnl/min).

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 159-160

41
[ 2770-11-8 ]
[ 145729-29-9 ]
cyclohexyl-{4-[2-(4-chlorophenoxy)phenylamino]-piperidin-1-yl}-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%		Preparation of {4-[2-(4-chlorophenoxy)phenylamino]-piperidin-l-yl}- cyclohexylmethanone STX1702 C24H29ClN2O2, MW: 396.9785 EPO <DP n="166"/>To a solution of 2-(4-chlorophenoxy)phenylamine (100 mg, 0.49 mmol), 1- cyclohexanecarbonyl-4-piperidone (154 mg, 0.735 mmol) and acetic acid (147 mg, 2.45 mmol) in DCE (1.5 ml) was added sodium triacetoxyborohydride (260 mg, 1.23 mmol). This solution was then heated at 1000C for 15 minutes in a CEM discover microwave (fixed hold time set to on). Further l-cyclohexanecarbonyl-4-piperidone (50 mg, 0.24 mmol) was added and this reaction mixture was again heated at 1000C for 10 minutes in the CEM discover microwave (fixed hold time set to on). The reaction mixture was then quenched with saturated aqueous sodium bicarbonate solution (5 ml) and extraction with ethyl acetate (3 x 5 ml) followed. The combined organics were dried (MgSO4), filtered and concentrated in vacuo and purification by flash chromatography proceeded (eluant: 8:2 hexane: ethyl acetate) to provide the title compound as a transparent oil (58 mg, 30%). 1H NMR (270 MHz, CDCl3): delta 1.12-1.89 (12H, m, 12 x CH), 2.03-2.16 (2H5 m, 2 x CH)3 2.40-2.46 (IH, m, CH), 2.83 (2H, 't', J= 11.1 Hz, CH2), 3.15 (IH, 't J= 12.4 Hz, CH), 3.49-3.54 (IH, m, CH), 3.83 (IH, bd, J= 13.9 Hz, CH), 4.0 (IH, s, CH)5 4.42 (IH, d, J= 14.1 Hz, NH)5 6.60-6.66 (IH, td5 J= 1.2, 1.5, 7.8 Hz, ArH)5 6.73-6.77 (IH5 dd5 J = 1.2, 8.2 Hz, ArH), 6.78-6.82 (IH, dd, J = 1.2, 7.9 Hz, ArH), 6.84-6.91 (2H, m, ArH)5 7.00- 7.06 (IH5 td, J = 1.5, 0.8, 7.5 Hz, ArH), 7.19-7.26 ppm (2H, m, ArH). 13C NMR (67.93 MHz, CDC13): delta 26.0, 29.4, 29.6, 32.2, 33.3, 40.5, 44.1, 49.9, 112.2, 117.2, 118.8, 119.6, 125.3, 127.9, 129.8, 138.9, 143.0, 156.1, 174.6 ppm LCMS: M+H: 413.47 HPLC: 100% (retention time 3.210 min, isocratic 90% acetonitrile : 10% water, 1 ml/min).

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 163-164

42
[ 19202-11-0 ]
[ 2770-11-8 ]
1-{4-[2-(4-chlorophenoxy)phenylamino]-piperidin-1-yl}-2-phenylethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%		Preparation of l-{4-[2-(4-chlorophenoxy)phenylamino]-piperidin-l-yl}-2- phenylethanone STX1647 C25H25ClN2O2, MW: 420.9379To a solution of 2-(4-chlorophenoxy)phenylamine (100 mg, 0.45 mmol), 1-phenylacetyl- 4-piperidone (144 mg, 0.735 mmol) and acetic acid (147 mg, 2.45 mmol) in DCE (1.5 ml) was added sodium triacetoxyborohydride (260 mg, 1.23 mmol). This solution was then heated at 1000C for 15 minutes in a CEM discover microwave (fixed hold time set to on). The reaction mixture was then quenched with saturated aqueous sodium bicarbonate solution (5 ml) and extraction with ethyl acetate (3 x 5 ml) followed. The combined organics were concentrated in vacuo and purification by flash chromatography proceeded (eluant: 8:2 hexane: ethyl acetate) to provide the title compound as a transparent oil (69 mg, 36%). 1H NMR (270 MHz, CDCl3): delta 1.03-1.09 (IH, m, CH), 1.22-1.31 (IH, m, EPO <DP n="163"/>CH), 1.87-1.91 (IH3 m, CH), 1.99-2.04 (IH5 m, CH), 2.80-2.91 (IH, m, CH), 3.11-3.18 (IH, m, CH), 3.43-3.52 (IH, m, CH), 3.68-3.76 (3H, m, CH2 + CH), 3.95 (IH, s, NH), 4.39-4.45 (IH, m, CH), 6.55-6.62 (IH, td, J= 1.2, 1.5, 7.4 Hz, ArH), 6.68-6.71 (IH, dd, J = 1.5, 8.2 Hz, ArH)3 6.73-6.77 (IH, dd, J = 1.53 8.1 Hz, ArH)3 6.79-6.84 (2H, m, ArH), 6.95-7.01 (IH, td, J = 1.5, 0.7, 7.8 Hz, ArH), 7.16-7.32 ppm (7H, m, ArH). 13C NMR (67.93 MHz, CDC13): delta 32.0, 32.5, 40.7, 41.3, 44.9, 49.6, 112.2, 117.2, 118.8, 119.6, 125.3, 126.9, 127.9, 128.6, 128.9, 129.8, 135.1, 138.8, 143.0, 156.1, 169.4 ppm. LCMS: M+H: 399.49 HPLC: 99.17% (2.675 min, isocratic 90% acetonitrile, 10% water at 1 ml/min).

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 160-161

43
[ 50492-23-4 ]
[ 2770-11-8 ]
1-(4-(2-(4-chlorophenoxy)phenylamino)azepan-1-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%		Preparation of l-(4-(2-(4-chIorophenoxy)phenylamino)azepan-l-yI)ethanoneSTX1762 C20H23ClN2O2, MW: 358.86To a solution of 2-(4-chlorophenoxy)phenylamine (113 mg, 0.51 mmol), 1-acetylazepan-4-one (159 mg, 1.02 mmol) and acetic acid (153 mg, 2.55 mmol) in DCE (4 ml), was added sodium triacetoxyborohydride (270 mg, 1.28 mmol). The reaction mixture was allowed to stir at room temperature for 10 days. On return, the reaction was quenched with saturated aqueous sodium sodium bicarbonateonate (15 ml) and extracted with ethyl acetate (2 x 15 ml). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography then proceeded (eluent; 9:1 hexane:ethyl acetate to ethyl acetate) to afford the title compound as a pale yellow oil (67.1 mg, 37%).1H NMR (270 MHz, CDCl3): delta 1.49-2.27 (9H, m, 3 x CH2, CH3), 3.30- 3.72 (5H, m, 5 x CH), 4.10 (IH, br s, NH), 6.59-6.67 (2H, m, Ar-H), 6.78-6.89 (3H, m, Ar-H), 7.00-7.08 (IH, m, Ar-H), 7.21-7.24 ppm (2H, m, Ar-H). 13C NMR (67.93 MHz, CDC13): delta 21.9, 24.2, 25.3, 32.8, 33.0, 34.2, 35.2, 42.0, 45.0, 45.1, 48.3, 51.0, 52.0, 112.2, 118.6, 118.7, 125.4, 129.7, 129.8, 139.0, 142.8, 156.1, 156.2, 170.5 ppm. LCMS: EPO <DP n="171"/>M+U: 359.45 HPLC: 95.92% (2.677 min, isocratic 90% acetonitrile, 10% water at 1 ml/min).

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 168-169

44
[ 919119-04-3 ]
[ 2770-11-8 ]
1-(4-(2-(4-chlorophenoxy)phenylamino)-2-phenylpiperidin-1-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%		General Procedure for the Microwave-Assisted Preparation of the Final Piperidine Compounds.To a solution of 2-(4-chlorophenoxy)benzenamine (100 mg, 0.46 mmol), the relevant N-Acetyl-2-substituted-4-piperidone (0.92 mmol) and sodium triacetoxyborohydride (241 mg, 1.14 mmol) in DCE (1.5 ml) in a MW tube, was added acetic acid (83 mg, 1.38 mmol). The MW tube was sealed and heated at 14O0C for 10 rnins in a CEM discoverMW instrument. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate (10 ml) and extracted with ethyl acetate (3 x 10 ml). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (eluant: hexane: ethyl acetate) then proceeded to provide the desired compound.l-(4-(2-(4-Chlorophenoxy)phenylamino)-2-phenylpiperidin-l-yl)ethanone STX2419C25H25ClN2O2, MoI. Wt.: 420.93Yellow oil, 41.3 mg, 21%1H NMR: (CDCl3, 270 MHz): delta 1.55-1.76 (2H, m, 2 x CH), 2.10 (1.5H, s, CH3), 2.23 (1.5H3 s, CH3), 2.69-2.82 (2H, m, CH), 3.12-3.22 (0.5H, m, CH)3 3.37-3.48 (0.5H5 m,CH), 3.52-3.62 (0.5H, m, CH), 3.75 (0.5H, 'd', J- 14.1 Hz, CH), 3.87-4.02 (0.5H, br S3CH), 4.74 (0.5H3 'd J = 13.9 Hz3 CH)3 5.17-5.23 (0.5H3 m, CH)3 6.13-6.14 (0.5H3 m, EPO <DP n="223"/>CH), 6.57-6.68 (2H, m, Ar-H), 6.79 (IH, d, J= 7.9 Hz, Ar-H), 6.87 (2H, d, J= 7.7 Hz, Ar-H), 7.00 (IH, eq J = 6.7, 13.9 Hz, Ar-H), 7.19-7.46 ppm (7H, m, Ar-H). 13C NMR (CDCl3, 67.93 MHz): delta 21.6, 21.8, 32.5, 33.5, 34.5, 36.2, 37.4, 42.0, 45.8, 45.9, 50.6, 56.2, 112.2, 112.3, 117.5, 118.8, 119.6, 125.3, 125.8, 126.1, 126.5, 127.6, 128.0, 129.0, 129.4, 129.8, 138.2, 138.8, 143.1, 156.1, 167.3 ppm.HPLC: 2.355 min, 96.2% purity, (isocratic, 90% acetonitrile : 10% water at 1.0 ml/min) LCMS: 1.623 min, (95% MeOH : 5% water at 1.0 ml/min), ES": 419.42.

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 220-221

45
[ 1206-74-2 ]
[ 2770-11-8 ]
1-acetyl-5-[2-(4-chloro-phenoxy)-phenylamino]-2,3,4,5-tetrahydro-benzo[b]azepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%		l-Acetyl-5-[2-(4-Chloro-phenoxy)-phenylammo]-2,3,4,5-tetrahydro-benzo[b]azepine (CMS02033, STX2171) C24H23ClN2O2, MoI. Wt.: 406.90 EPO <DP n="241"/>To a mixture of l-BOC-2,3-dihydro-lH-quinolin-4-one (0.050 g, 0.25 mmol) and 2-(4- chlorophenoxy)-aniline (0.060 g, 0.27 mmol, 2.2 eq.) in toluene (5 mL) was added cUorotriisopropoxytitamum(TV) (0.3 mL, 2 eq.) and the resulting deep orange solution stirred at room temperature overnight. Saturated NaHCO3 solution (10 mL) was added and the phases separated. The organic layer was separated dried over anhydrous magnesium sulphate then filtered and evaporated. The residue was re-dissolved in THF (25 mL) and cooled to 0 0C under nitrogen. A solution of succinic acid (0.189 g, 1.6 mmol) in THF (5 mL) was added followed by IM borane tetrahydrofuran complex (1.6 mL, 2 eq.). The reaction was allowed to warm to room temperature before the addition of saturated NaHCtheta3 solution (100 mL). The volatile solvent was removed under reduced pressure then ethyl acetate (100 mL) was added and the layers separated. The organic layer was dried, evaporated and then purified by column chromatography (flashmasterIL, 50 g column) using 0-30% ethyl acetate/hexanes as eluent to give the desired product (21 mg, 21%) as a colourless foam which showed; Rf. 0.18 (20% ethyl acetate/hexanes)LRMS (EI+) m/z 429.47 (M+ + Na, 100%);HRMS (EI) calcd. for C24H23ClN2O2 (M+H-H) 407.1521, found 407.1523;

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 238-239

46
[ 32900-14-4 ]
[ 2770-11-8 ]
1-acetyl-{4-[2-(4-chloro-phenoxy)phenyl]amino}-7-methoxy-3,4-dihydro-2H-quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		l-Acetyl-{4-[2-(4-Chloro-phenoxy)-phenylamino]-7-methoxy-3,4-dihydro-2H- quinoline(CMS02064, STX2425) C24H23ClN2O3, MoI. Wt. : 422.90 EPO <DP n="244"/>To a mixture of l-Acetyl-7-Methoxy-2.3-dihydro-lH-quinolin-4-one (0.148 g, 0.68 mmol) and 2-(4-chlororhohenoxy)-aniline (0.163 g, 1.1 mmol, 2 eq.) in toluene (10 mL) was added chlorotriisopropoxy-titaniuin(rV) (0.4 mL, 2.4 eq.) and the resulting deep orange solution stirred at room temperature overnight. Saturated NaHCO3 solution (10 mL) was added and the phases separated. The organic layer was separated dried over anhydrous magnesium sulphate then filtered and evaporated. The residue was re-dissolved in THF (25 mL) and cooled to 0 0C under nitrogen. A solution of succinic acid (0.189 g, 1.6 mmol) in THF (5 mL) was added followed by IM borane tetrahydrofuran complex (1.6 mL, 2.4 eq.). The reaction was allowed to warm to room temperature before the addition of saturated NaHCO3 solution (100 mL). The volatile solvent was removed under reduced pressure then ethyl acetate (100 mL) was added and the layers separated. The organic layer was dried, evaporated and then purified by column chromatography (flashmasterIL 50 g column) using 0-30% ethyl acetate/hexanes as eluent to give the desired product (0.221 g, 78%) as a colourless foam which showed; 1H NMR (270 MHz, CDCl3) delta 1.89-2.01 (IH, m), 2.13-2.24 (IH, m), 2.21 (3H, s, NAc), 3.51-3.63(1H, m), 3.75 (3H, s, OCH3), 3.89-4.02 (IH, m), 4.50 (IH, t, J = 5.8 Hz), 6.68 (IH, dd, J = 7.4 and 1.5 Hz), 6.84-6.89 (4H, m), 7.06 (IH, dt, J = 7.4 and 1.5 Hz), 7.14 (IH, d, J = 8.7 Hz), 7.26 (2H, d, J = 9.1 Hz), (9-CH not integrating due to hydrogen bonding); LC/MS (AP+) tr = 1.42 min ( >99 %), m/z 421.01 (M-H)+; LRMS (AP+) m/z 421.01 ( (M-H)+, 100%); HPLC tr = 2.95 min (97.07 %).

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 241-242

47
[ 2770-11-8 ]
[ 79099-07-3 ]
4-[2-(4-chlorophenoxy)phenylamino]-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		Preparation of 4-[2-(4-chlorophenoxy)phenylamino]-piperidine-l-carboxylic acid tert-butyl ester STX1680 C22H27ClN2O3, MW: 402.93To a solution of 2-(4-chlorophenoxy)phenylamine (900 mg, 4.10 mmol), l-BOC-4- piperidone (1.76 g, 8.82 mmol) and acetic acid (1.32 g, 22.05 mmol) in DCE (15 ml) was added sodium triacetoxyborohydride (2.34 g, 11.04 mmol). This solution was then split into 4 microwave tubes, which were individually heated at 850C for 15 minutes in a CEM EPO <DP n="149"/>discover microwave (fixed hold time set to on). The contents of each tube were added to a saturated aqueous sodium bicarbonate solution (25 ml) with extraction with ethyl acetate (3 x 25 ml) following. The combined organics were dried (MgSO4), filtered and concentrated in vacuo and purification by flash chromatography proceeded (eluant: 3:1 to 1:1 hexane:DCM) to provide a white solid. Recrystallisation was then carried out, which afforded the title compound as a white crystalline solid (1.122 g, 68%). M.Pt. 112- 113.40C 1H NMR (300 MHz, CDCl3): delta 1.165-1.308 (2H, m, 2 x CH), 1.380 (9H, s, t- Bu)5 1.909-1.974 (2H5 m, 2 x CH)5 2.822-2.897 (2H5 'f, J= 11.3 Hz5 CH2), 3.385-3.45 (IH, m, CH)5 3.85-4.02 (3H, m, 2 x CH5 NH)5 6.542-6.597 (IH5 td, ArH)5 6.674-6.842 (4H, m, ArH)5 6.946-7.002 (IH5 td, ArH)5 7.157-7.209 ppm (2H5 m, ArH). 13C NMR (67.93 MHz5 CDC13): delta 28.5, 32.3, 43.0, 49.8, 79.7, 112.2, 117.O5 118.7, 119.6, 125.3, 127.8, 129.7, 139.O5 143.0, 154.8, 156.2 ppm. LCMS: M+H: 403.46 HPLC: 99.53% (4.9411 min, isocratic, 90% acetonitrile: 10% water, 1 ml/min). CHN: Expected, N = 6.95%, C - 65.58%, H = 6.75% Observed, N = 6.82%, C = 65.5%, H = 6.71%

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 146-147

48
[ 32499-64-2 ]
[ 2770-11-8 ]
ethyl 3-(2-(4-chlorophenoxy)phenylamino)-8-azabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%		Preparation of ethyl 3-(2-(4-chlorophenoxy)phenyIamino)-8-azabicyclo[3.2.1]octane- 8-carboxylate STX1764 C22H25ClN2O3, MW: 400.9To a solution of 2-(4-chlorophenoxy)phenylamine (113 mg, 0.51 mmol), N- (ethoxycarbonyl)-tropinone (201 mg, 1.02 mmol) and acetic acid (153 mg, 2.55 mmol) in DCE (4 ml), was added sodium triacetoxyborohydride (270 mg, 1.28 mmol). The reaction mixture was allowed to stir at room temperature for 10 days. On return, the reaction was quenched with saturated aqueous sodium sodium bicarbonateonate (15 ml) and extracted with ethyl acetate (2 x 15 ml). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography then proceeded (eluent; 9:1 hexane:ethyl acetate to ethyl acetate) to afford the title compound as a pale yellow oil (43 mg, 21%).1H NMR (270 MHz, CDCl3): delta 1.24 (3H, t, J = 7.2 Hz, CH3), 1.65-1.90 (6H, m, 2 x CH2, 2 x CH), 2.03-2.21 (2H, m, 2 x CH), 3.67-3.72 (IH, m, CH), 4.05-4.30 (3H, m, CH2, NH), 4.39 (IH, d, J = 5.7 Hz, CH), 6.57-6.67 (2H, m, Ar-H), 6.85-6.89 (3H, m, Ar-H), 7.02-7.09 (IH, td, J = 1.5, 1.0, 7.7 Hz, Ar-H), 7.21-7.27 ppm (2H, m, Ar-H). 13C NMR (67.93 MHz, CDC13): delta 14.9, 27.0, 27.5, 35.0, 35.6, 44.7, 52.6, 61.0, 111.3, 116.8, 118.1, 120.1, 125.7, 127.7, 129.7, 139.3, 142.3, 153.8, 156.5, ppm. LCMS: M+H: 401.51 HPLC: 97.42% (4.106 min, isocratic 90% acetonitrile, 10% water at 1 rnl/min).

Reference： [1]Patent: WO2007/3934,2007,A2 .Location in patent: Page/Page column 170

49
[ 86604-86-6 ]
[ 2770-11-8 ]
[ 1049799-23-6 ]

Reference： [1]European Journal of Medicinal Chemistry,2008,vol. 43,p. 1390 - 1402

50
[ 2941-48-2 ]
[ 2770-11-8 ]
[ 1049799-46-3 ]

Reference： [1]European Journal of Medicinal Chemistry,2008,vol. 43,p. 1390 - 1402

51
[ 2770-11-8 ]
[ 4887-95-0 ]
5⁽⁶⁾-chloro-2-[2-(4'-chlorophenoxy)anilino]-1H-benzimidazole hydrochloride [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2008,vol. 43,p. 1390 - 1402

52
[ 2770-11-8 ]
[ 552-89-6 ]
[ 1158910-21-4 ]

Yield	Reaction Conditions	Operation in experiment
77%		To a solution of 2-(4-chloro-phenoxy)-phenylamine (150 mg, 0.68 mmol) and 2- nitrobenzaldehyde (310 mg, 2.04 mmol) in DCE (3.5 ml) was added acetic acid (0.36 ml) and sodium triacetoxyborohydride (0.36 g, 1.7 mmol). The resulting reaction mixture was heated in a microwave at 140 C for 10 min. NaHCO3 was then added and the mixture was repeatedly extracted with EtOAc. The organic layers were combined, dried (MgSO4), filtered and evaporated in vacuo. The crude mixture was purified using flash chromatography (0-100 % EtOAc in hexane) to afford the title compound as a yellow solid, 194 mg, 77 % yield.R.f. 0.63 (1:1, EtOAc: Hexane),LCMS: U= 1.66 min (95 % MeOH in H2O), m/z M+H 355.48,HPLC: U= 6.6 min (90 % ACN in H2O), 92 %,1H NMR (CDCl3, 270 MHz): delta 4.75 (2H, s, CH2), 4.97 (IH, s, NH), 6.52 (IH, dd, J= 1.2, 7.9 Hz, ArH), 6.66 (IH, td, J= 1.5, 7.7 Hz, ArH), 6.83-6.99 (4H, m, ArH), 7.21-7.27 (2H, m, ArH), 7.37-7.44 (IH, m, ArH), 7.54-7.57 (2H, m, ArH), 8.05 (IH, dd, J= 1.0, 7.7 Hz, ArH).

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 87

53
[ 2770-11-8 ]
[ 610-14-0 ]
[ 1158910-16-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine; In dichloromethane; at 0 - 20℃; for 0.5h;	To a solution of 2-(4-chloro-phenoxy)-phenylamine (200 mg, 0.91 mmol) in DCM (5 ml) at 0 C was added 2-nitrobenzoyl chloride (338 mg, 1.82 mmol) and TEA (0.15 ml). The reaction was then stirred at r.t. for 30 min. NaHCO3 was added and the mixture was extracted with DCM, dried (MgSO4) and purified by flash chromatography (0-100 % DCM in hexane) to yield the desired product, 258 mg, 77 % yield. LCMS: ttau= 1.91 min (80 % MeOH in water), m/z M-H 367.09, HPLC: tr= 2.16 min (90 % ACN in water), 90 %,1H NMR (CDCl3, 270 MHz,): delta 6.83 (IH, dd, J = 1.4, 8.0 Hz, ArH), 6.91-6.99 (2H, m, ArH), 7.07 (IH, td, J= 1.6, 8.0 Hz, ArH), 7.17 (IH, t, J= 7.2Hz, ArH), 7.24-7.31 (2H, m, ArH), 7.48 (IH, dd, J= 1.4, 7.2Hz, ArH), 7.58 (IH, td, J = 1.4, 7.5 Hz, ArH), 7.65 (IH, dd, J= 1.1, 7.4 Hz, AiH), 8.00-8.06 (2H, m, ArH and NH), 8.47 (IH, dd, J= 1.1, 8.0 Hz, ArH).

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 74

54
[ 2770-11-8 ]
[ 5234-26-4 ]
C₂₂H₁₉ClN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 2-(4-chloro-phenoxy)-phenylamine (298 mg, 1.4 mmol), N-(2-acetyl- phenyl)-acetamide, (200 mg, 1.13 mmol) and chlorotriisopropoxytitanium IV (0.53 ml, 2.26 mmol) in toluene (15 ml) was stirred at r.t. for 4 days. NaHCO3 was added and the mixture was extracted repeatedly with EtOAc, dried (MgSO4) and evaporated to dryness. The residue was re-dissolved in THF (20 ml) and cooled to 0 C, to this was added succinic acid (270 mg, 2.26 mmol) and borane (IM in THF, 2.3 ml, 2.26 mmol). The reaction was slowly warmed to r.t. and stirred for 8 h. NaHCO3 was added and the volatile solvents removed in vacuo, the mixture was then extracted with EtOAc and dried (MgSO4). The crude material was purified by flash chromatography (0-100 % DCM in hexane) to yield the product, 79 mg, 19 % yield. LCMS: tr= 1.42 min (95 % MeOH in water), m/z M-H 365.33, HPLC: U= 4.49 min (90 % ACN in water), 97 %,1H NMR (CDCl3, 270 MHz,): delta 1.17 (3H, X, J = 12 Hz, CH3CH2), 1.56 (3H, d, J = 6.7 Hz, CH3CH), 3.10 (2H, q, J= 14.1 Hz, CH2), 4.22 (IH, d, J= 6.0 Hz, NH), 4.53 (IH, q, J = 13.3 Hz, CH), 4.59 (IH, br.s, NH), 6.66-6.93 (7H, m, ArH), 7.01 (IH, td, J= 7.9, 1.5 Hz, ArH), 7.16-7.31 (4H, m, ArH).13C NMR (CDCl3, 68 MHz): 14.9, 19.9 (CH3), 38.1 (CH2), 50.9 (CH), 111.1, 113.6, 117.0, 118.0, 118.6, 119.5, 125.5, 126.5 (ArCH), 128.6, 127.8 (ArC), 128.3, 129.7 (ArCH), 13.7, 143.3, 146.7, 156.4 (ArC).HRMS: Calcd for C22H23ClN2O (M+Na)+ 389.1386, found (M+Na)+ 389.1391.

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 92

55
[ 7463-31-2 ]
[ 2770-11-8 ]
[ 1158910-03-2 ]

Yield	Reaction Conditions	Operation in experiment
40%		<strong>[2770-11-8]2-(4-Chlorophenoxy)aniline</strong> (100 mg, 0.4552 mmol, 1.1 eq) and N-Q- acetylphenyl)acetamide (73 mg, 0.4120 mmol, 1 eq) were stirred in dry dichloromethane <n="110"/>(DCM) at room temperature for 10 min. Tri-isopropoxytitanium chloride (215 muL, 0.9002 mmol, 2.2 eq) was added to the reaction mixture which was stirred at room temperature for an additional 10 min. Sodium triacetoxyborohydride (438 mg, 2.0667 mmol, 5 eq) and acetic acid (3 drops) were added to the reaction mixture which was stirred at room temperature for 16 h. The reaction mixture was then poured onto a solution of saturated aqueous sodium bicarbonate (100 mL) and extracted with DCM (120 mL). The organic layer was washed with brine (120 mL), dried over MgSO4, filtered and concentrated to give the crude as a yellow foam. Purification of the crude by flash chromatography (ISCO) eluting with a gradient [from 100% petroleum ether (PE) to 100% EtOAc] gave the title compound (62 mg, 40%) as a white solid.1H NMR (270 MHz, CDCl3) delta 1.45 (3H, d, J = 7.0 Hz, CH3), 2.09 (3H, s, CH3), 4.39-4.52 (2H, m, CH + NH), 6.41-6.46 (IH, m, ArH), 6.51-6.60 (IH, m, ArH), 6.75-6.95 (5H, m, ArH), 7.01-7.08 (IH, m, ArH), 7.18-7.29 (2H, m, ArH), 7.35-7.42 (2H, m, ArH), 7.70 (IH, br s, NH); 13C NMR (67.5 MHz, CDCl3) delta 24.7, 25.2, 53.2, 113.0, 117.0, 117.1,118.6, 118.8, 119.2, 121.7, 125.3, 129.4, 129.7, 138.4, 139.4, 142.6, 146.3, 156.4, 168.5 ;LCMS (90% MeOH and 10% H2O; Symmetry Ci8 reverse phase column) tr = 2.25 min;(ES"), m/z 381 (35ClM', 75%), 383 (37ClM", 25%); HRMS (ESI) calcd. for C22H22ClN2O2(M+H)+ 381.1364, found 381.1369.

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 107-108

56
[ 22948-94-3 ]
[ 2770-11-8 ]
[ 1158910-00-9 ]

Yield	Reaction Conditions	Operation in experiment
78%		A solution of the aniline (250 mg, 1.14 mmol), l-acetyl-3-indolecarboxaldehyde (107 mg, 0.57 mmol), NaBH(OAc)3 (302 mg, 1.43 mmol) and AcOH (205 mg, 3.42 mmol) in 1,2-DCE (3 ml) was stirred at room temperature for 16 h. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate (5 ml) and extracted with EtOAc (3 x 5 ml). The combined organics were dried (MgSO4), filtered and concentrated in vacuo before purification by flash chromatography (eluant; 8:2 hexane:EtOAc to EtOAc) proceeded to afford the desired product which was recrystallised from EtOAc and hexane to afford a cream solid (174.1 mg, 78%).1H NMR: (CDCl3, 270 MHz): delta 2.56 (3H, s, CH3), 3.77 (IH, br s, NH), 4.47 (2H, br s,CH2), 6.65-7.50 (12H, m, ArH), 8.41 ppm (IH, d, J= 7.9 Hz, ArH). 13C NMR: (CDCl3, 67.93 MHz): 5 24.1, 39.7, 112.1, 117.0, 117.6, 118.5, 119.0, 119.6,120.1, 123.0, 123.7, 125.5, 125.7, 128.0, 129.7, 136.1, 140.0, 143.5, 156.2, 168.6 ppm.LCMS: 1.550 min, (95% MeOH : 5% water at 1.0 ml/min), AP": 389.20.HPLC: 3.410 min, 95.90% purity, (isocratic, 90% acetonitrile : 10% water at 1.0 ml/min).HRMS (MicroTOF): C23H20ClN2O2 requires 391.1208, found 391.1194. M.Pt. 107-1080C.

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 105

57
[ 765917-13-3 ]
[ 2770-11-8 ]
[ 1158910-10-1 ]

Yield	Reaction Conditions	Operation in experiment
91%		<strong>[2770-11-8]2-(4-Chlorophenoxy)aniline</strong> (245 mg, 1.118 mmol, 1 eq) and l-acetyl-N-(3-acetylphenyl)-N-ethylpiperidine-4-carboxamide (250 mg, 1.230 mmol, 1.1 eq) were stirred in dry dichloromethane (DCM) (2 mL) at room temperature for 10 min. Tri-isopropoxytitanium chloride (534 muL, 2.236 mmol, 2 eq) was added to the reaction mixture which was stirred at room temperature for 16 hours. Sodium triacetoxyborohydride (947 mg, 4.472 mmol, 4 eq) was then added to the reaction mixture and was stirred at room temperature for a further 24 h. The reaction mixture was then poured into saturated aqueous sodium <n="118"/>bicarbonate (100 mL) and extracted with DCM (120 mL). The organic layer was washed with brine (120 mL), dried over MgSO4, filtered and concentrated to give the crude as a yellow oil. Purification of the crude by flash chromatography (ISCO) eluting with a gradient [0-10% MeOH/ DCM] gave (437 mg, 91%) as a pale yellow oil. 1H NMR (270 MHz, CDCl3) delta 1.45 (3H, d, J = 8.1 Hz, CH3), 2.02-2.18 (2eta, m, CH2), 2.58 (2H, t, J = 10.8 Hz, CH2), 3.77 (2eta, X, J= 9.7 Hz, CH2), 4.50 (2eta, m, NH and CH), 6.47-6.62 (2eta, m, Ar) 6.77-6.96 (4H, m, Ar), 7.09 (IH, d, J= 8.1 Hz, Ar), 7.22-7.32 (3H, m, Ar), 7.48 (IH, dd, J = 2.4, 8.1 Hz, Ar), 7.59 (IH, m, Ar). LCMS (90% MeOH and 10% H2O; Symmetry C18 reverse phase column) tx = 2.73 min; (ES+), m/z 407. ,2. HPLC 98.56 % purity.

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 115-116

58
[ 325715-13-7 ]
[ 2770-11-8 ]
[ 1158910-06-5 ]

Yield	Reaction Conditions	Operation in experiment
17%		<strong>[2770-11-8]2-(4-Chlorophenoxy)aniline</strong> (95 mg, 0.4314 mmol, 1.1 eq) and N-(3-acetylpheny I)-N- methylacetamide (75 mg, 0.3922 mmol, 1 eq) were stirred in dry dichloromethane (DCM) at room temperature for 10 min. Tri-isopropoxytitanium chloride (187.4 muL, 0.7844 mmol, 2 eq) was added to the reaction mixture which was stirred at room temperature for 16 hours. Sodium triacetoxyborohydride (332.4 mg, 1.568 mmol, 4 eq) was then added to the reaction mixture and was stirred at room temperature for a further 24 h. The reaction mixture was then poured onto a solution of saturated aqueous sodium bicarbonate (100 mL) and extracted with DCM (120 mL). The organic layer was washed with brine (120 rriL), dried over MgSO4, filtered and concentrated to give the crude as a yellow oil. Purification of the crude by flash chromatography (ISCO) eluting with a gradient [from 100% dichloromethane (DCM) to 5% MeOH in dichloromethane] gave (26 mg, 17 %) as an off-white solid.Mp 127-131 C; 1H NMR (270 MHz, CDCl3) delta 1.45 (3H, d, J= 7.0 Hz, CH3), 1.72 (3H, s, CH3), 3.22 (3H, s, NCH3), 4.51-4.60 (2H, m, CH and NH) 6.37 (IH, d, J = 6.7 Hz, ArH), 6.59 (IH, dt, J = 1.3, 6.7 Hz ArH), 6.75-6.97 (4H, m, ArH), 6.90-7.10 (2H, m, <n="114"/>ArH), 7.22-7.39 (4H, m, ArH); 13C NMR (67.5 MHz, CDCl3) delta 22.1, 25.2, 37.3, 53.5,112.9, 117.2, 118.8, 119.2, 124.5, 125.0, 125.2, 125.4, 129.8, 130.0, 134.1, 138.9, 142.8, 145.0, 147.1, 156.2, 170.5 LCMS (90% MeOH and 10% H2O; Symmetry C18 reverse phase column) tr = 2.58 min; (ES+), m/z 395.3 (35ClM", 75%), 383 (37ClM', 25%); HRMS (ESI) calcd. for C23H23ClN2O2 (M+H)+ 395.1507, found 395.1511. Anal.calcd for C23H23ClN2O2; N 7.09, C 69.95, H 5.87 % found N 6.81, C 69.8, H 6.13 %

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 111-112

59
[ 2770-11-8 ]
[ 200630-96-2 ]
[ 1158910-07-6 ]

Yield	Reaction Conditions	Operation in experiment
26%		<strong>[2770-11-8]2-(4-Chlorophenoxy)aniline</strong> (200 mg, 0.9107 mmol, 1.1 eq) and JV-(3-acetylphenyl)-iV- ethylacetamide (169 mg, 0.827 mmol, 1 eq) were stirred in dry dichloromethane (DCM) at room temperature for 10 min. Tri-isopropoxytitanium chloride (395 muL, 1.654 mmol, 2 eq) was added to the reaction mixture which was stirred at room temperature for 16 hours. Sodium triacetoxyborohydride (700 mg, 3.308 mmol, 4 eq) was then added to the reaction mixture and was stirred at room temperature for a further 24 h. The reaction mixture was then poured onto a solution of saturated aqueous sodium bicarbonate (100 mL) and extracted with DCM (120 mL). The organic layer was washed with brine (120 mL), dried over MgSO4, filtered and concentrated to give the crude as a yellow oil. Purification of the crude by flash chromatography (ISCO) eluting with a gradient [from 25% ethyl acetate in petrol ether to 50% ethyl acetate in petrol ether] gave (87 mg, 26 %) as a white solid. <n="115"/>1H NMR (270 MHz, CDCl3) delta 1.05 (3H, t, J = 8.1 Hz, CH3), 1.49 (3eta, d, J = 6.4 Hz CH3), 1.67 (3H, s, CH3), 3.68 (2H, q, J= 8.1 Hz, CH2), 4.45-4.60 (2H, m, NH and CH) 6.37 (1eta, d, J = 8.2 Hz, ArH), 6.57 (IH, dt, J = 1.4, 8.2 Hz ArH), 6.75-7.06 (6H, m, ArH), 7.23-7.39 (4H, m, ArH); 13C NMR (67.5 MHz, CDCl3) delta 13.1, 22.8, 25.0, 43.8, 52.8, 112.0, 112.9, 117.2, 118.7, 119.3, 125.0, 126.1, 126.5, 128. 0, 129.8, 130.0, 138.0, 139.1, 142.8, 147.1, 156.5, 169.9 LCMS (90% MeOH and 10% H2O; Symmetry C18 reverse phase column) tr = 2.88 min; (ES+), m/z 409.2 (35ClM', 75%), 383 (37ClM', 25%); HRMS (ESI) calcd. for C24H25ClN2O2 (M+H)+ 409.1605, found 409.1689. 99.48% purity.

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 112-113

60
[ 908515-96-8 ]
[ 2770-11-8 ]
[ 1158910-04-3 ]

Yield	Reaction Conditions	Operation in experiment
10%		<strong>[2770-11-8]2-(4-Chlorophenoxy)aniline</strong> (25 mg, 0.1138 mmol, 1.1 eq) and l-acetyl-7V-(2- acetylphenyl)piperidine-4-carboxamide (30 mg, 0.1040 mmol, 1 eq) were stirred in dry dichloromethane (DCM) at room temperature for 10 min. Tri-isopropoxytitanium chloride (55 muL, 0.2303 mmol, 2.2 eq) was added to the reaction mixture which was stirred at room temperature for an additional 10 min. Sodium triacetoxyborohydride (110 mg, 0.5190 mmol, 5 eq) and acetic acid (3 drops) were added to the reaction mixture which was stirred at room temperature for 16 h. The reaction mixture was then poured onto a solution of saturated aqueous sodium bicarbonate (50 mL) and extracted with DCM (30 mL). The organic layer was washed with brine (50 mL), dried over MgSO4, filtered and concentrated to give the crude as a yellow oil. Purification of the crude by flash chromatography (ISCO) eluting with a gradient [from 100% petroleum ether (PE) to 100% EtOAc] gave the title compound (5 mg, 10%) as a clear oil.1H NMR (270 MHz, CDCl3) delta 1.44 (3H, d, J = 7.5 Hz, CH3), 1.63-1.68 (2H, m, CH2), 1.82-1.98 (2H, m, CH2), 2.02 (3H, s, CH3), 2.38-2.45 (IH, m, CH), 2.65-2.69 (2H, m, CH2), 3.09-3.21 (2H, m, CH2), 4.40-4.48 (2H, m, CH + NH), 6.40-6.44 (IH, m, ArH), 6.51-6.58 (IH, m, ArH), 6.74-6.95 (4H, m, ArH), 7.05-7.11 (IH, m, ArH), 7.19-7.22 (3H, m, ArH), 7.35-7.49 (3H, m, NH + ArH); 13C NMR (67.5 MHz, CDCl3) delta 21.6, 25.2, 41.0, 45.8, 53.2, 60.5, 113.0, 117.0, 117.1, 118.6, 118.8, 119.2, 119.3, 119.4, 119.6, 125.3, 129.5, 129.7, 129.8, 139.4, 142.6, 146.3, 168.5, 172.3; LCMS (90% MeOH and 10% H2O; Symmetry Ci8 reverse phase column) tr = 2.38 min; (ES"), m/z 492 (35ClM", 75%), 494 (37ClM", 25%); HRMS (ESI) calcd. for C28H31ClN3O3 (M+H)+ 492.2048, found 492.2038.

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 108-109

61
[ 1090017-04-1 ]
[ 2770-11-8 ]
[ 1158910-05-4 ]

Yield	Reaction Conditions	Operation in experiment
18%		<strong>[2770-11-8]2-(4-Chlorophenoxy)aniline</strong> (137 mg, 0.6237 mmol, 1.1 eq) and l-acetyl-N-(3- acetylphenyl)piperidine-4-carboxamide (160 mg, 0.5549 mmol, 1 eq) were stirred in dry dichloromethane (DCM) at room temperature for 10 min. Tri-isopropoxytitanium chloride (295 muL, 1.2351 mmol, 2.2 eq) was added to the reaction mixture which was stirred at room temperature for an additional 10 min. Sodium triacetoxyborohydride (590 mg, 2.7838 mmol, 5 eq) and acetic acid (3 drops) were added to the reaction mixture which was stirred at room temperature for 16 h. The reaction mixture was then poured onto a solution of saturated aqueous sodium bicarbonate (100 mL) and extracted with DCM (80 mL). The organic layer was washed with brine (100 mL), dried over MgSO4, filtered and concentrated to give the crude as a yellow oil. Purification of the crude by flash chromatography (ISCO) eluting with a gradient [from 100% petroleum ether (PE) to 100% EtOAc] gave the title compound (48 mg, 18%) as a clear oil.1R NMR (270 MHz, CDCl3) delta 1.43 (3H, d, J = 7.0 Hz, CH3), 1.60-1.95 (4H, m, 2chiCH2), 2.07 (3H, s, CH3), 2.38-2.52 (IH, m, CH), 2.55-2.72 (2H, m, CH2), 3.01-3.15 (2H, m, CH2), 4.36-4.50 (2H, m, CH + NH), 6.40-6.48 (IH, m, ArH), 6.52-6.60 (IH, m, ArH), 6.75-6.95 (4H, m, ArH), 7.04-7.09 (IH, m, ArH), 7.19-7.28 (3H, m, ArH), 7.35-7.50 (2H, m, ArH), 7.78 (IH, br s, NH); 13C NMR (67.5 MHz, CDCl3) delta 21.6, 25.2, 41.0, 45.8, 53.3, 60.5, 113.0, 117.0, 117.1, 118.6, 118.8, 119.2, 119.4, 119.6, 125.3, 129.4, 129.7, <n="113"/>138.4, 139.4, 142.6, 146.4, 156.3, 169.1, 172.5; LCMS (90% MeOH and 10% H2O;Symmetry C18 reverse phase column) ttau = 2.32 min; (ES"), m/z 492 ( ?3"5C, lM", 75%), 494 (37ClM", 25%); HRMS (ESI) calcd. for C28H31ClN3O3 (M+H)+ 492.2048, found 492.2051.

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 110-111

62
[ 1158910-33-8 ]
[ 2770-11-8 ]
[ 1158910-08-7 ]

Yield	Reaction Conditions	Operation in experiment
		<strong>[2770-11-8]2-(4-Chlorophenoxy)aniline</strong> (95 mg, 0.431 mmol, 1 eq) and l-acetyl-N-(3-acetylphenyl)- N-ethylpiperidine-4-carboxamide (150 mg, 0.474 mmol, 1.1 eq) were stirred in dry dichloromethane (DCM) (2 mL) at room temperature for 10 min. Tri-isopropoxytitanium chloride (206 muL, 1.654 mmol, 2 eq) was added to the reaction mixture which was stirred at room temperature for 16 hours. Sodium triacetoxyborohydride (365 mg, 1.724 mmol, 4 eq) was then added to the reaction mixture and was stirred at room temperature for a further 24 h. The reaction mixture was then poured onto a solution of saturated aqueous sodium bicarbonate (100 mL) and extracted with DCM (120 mL). The organic layer was <n="116"/>washed with brine (120 mL), dried over MgSO4, filtered and concentrated to give the crude as a yellow oil. Purification of the crude by flash chromatography (ISCO) eluting with a gradient [0-10% MeOH/ DCM] gave as a pale yellow oil. 1H NMR (270 MHz, CDCl3) delta 0.98 (3H, dt, J= 3.1, 7.0 Hz, CH3), 1.25 (1eta, m, CH2), 1.50 (3H, d, J = 6.2 Hz CH3), 1.50-1.71 (3H, m, CH2), 1.95 (3eta, d, J= 7.2 Hz) 2.05-2.20 (2H, m, CH2), 2.40 and 2.65 (IH, m, CH), 3.50-3.72 (3eta, m, CH2), 4.30-4.61 (3eta, m, CH and NH), 6.32 (1eta, d, J = 7.8 Hz, ArH), 6.55 (IH, q, J= 7.3 Hz, Ar), 6.70-6.90 (4H, m, Ar), 6.95-7.05 (2H, m, Ar), 7.20-7.42 (4H, m, Ar); LCMS (90% MeOH and 10% H2O; Symmetry C18 reverse phase column) U = 2.38 min; (ES+), m/z 520.3; HRMS (ESI) calcd. for C30H35ClN3O3 (M+H)+ 520.2289, found 520.2343. HPLC 99.49% purity.

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 113-114

63
[ 1158910-34-9 ]
[ 2770-11-8 ]
[ 1158910-09-8 ]

Yield	Reaction Conditions	Operation in experiment
61%		<strong>[2770-11-8]2-(4-Chlorophenoxy)aniline</strong> (118 mg, 0.541 mmol, 1 eq) and l-acetyl-N-(3-acetylphenyl)-N-methylpiperidine-4-carboxarnide (180 mg, 0.595 mmol, 1.1 eq) were stirred in dry dichloromethane (DCM) (2 mL) at room temperature for 10 min. Tri-isopropoxytitanium chloride (284 muL, 1.19 mmol, 2 eq) was added to the reaction mixture which was stirred at room temperature for 16 hours. Sodium triacetoxyborohydride (504 mg, 2.38 mmol, 4 eq.) was then added to the reaction mixture and was stirred at room temperature for a further 24 h. The reaction mixture was then poured into aqueous sodium bicarbonate (100 <n="117"/>mL) and extracted with DCM (120 mL). The organic layer was washed with brine (120 mL), dried over MgSO4, filtered and concentrated to give the crude as a yellow oil. Purification of the crude by flash chromatography (ISCO) eluting with a gradient [0-10% MeOH/ DCM] gave (167 mg, 61 %) as a white foam. 1H NMR (270 MHz, CDCl3) delta 1.2- 1.38 (2H, m, CH2), 1.50 (3eta, d, J= 6.1 Hz, CH3), 1.55-1.80 (2eta, m, CH2), 1.90 (3eta, d, J = 6.7 Hz CH3), 2.10-2.30 (2H, m, CH2), 2.39 and 2.65 (1eta, m, CH2), 3.15 (3H, s, NCH3), 3.69 and 3.49 (1eta, d, J= 13.4 Hz, CH), 4.25-4.60 (3eta, m, NH and CH), 6.30 (1eta, d, J= 8.0 Hz, Ar) 6.55 (IH, q, J = 7.0 Hz, ArH), 6.75-6.95 (4H, m, ArH), 7.00-7.15 (2H, m, ArH), 7.23-7.51 (4H, m, ArH); LCMS (90% MeOH and 10% H2O; Symmetry C18 reverse phase column) U = 2.15 min; (ES+), m/z 506.4 HRMS (ESI) calcd. for C29H32ClN3O3 (M+H)+ 505.2132, found 506.2193. HPLC 100 % purity.

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 114-115

64
[ 2770-11-8 ]
[ 57091-71-1 ]
[ 1158909-95-5 ]

Yield	Reaction Conditions	Operation in experiment
44%		To a solution of 2-(4-chloro-phenoxy)-phenylamine (174 mg, 0.78 mmol) and N-(2- formyl-phenyl)-7V-methyl-acetamide (70 mg, 0.39 mmol) in DCE (2ml) was added NaHB(OAc)3 (210 mg, 0.98 mmol) and AcOH (0.07 ml). The resulting solution was stirred at r.t. for 2 h. NaHCO3 was then added and the mixture was extracted with DCM and dried (MgSO4). The crude product was purified by flash chromatography (0-100 % DCM in hexane) to yield the desired product as a brown oil, 65 mg, 44 % yield. <n="80"/>R.f. 0.51 (DCM),LCMS: U= 1.19 min (95 % MeOH in water), mJz M-H 378.93, HPLC: U = 2.64 min (90 % ACN in water), 98 %,1H NMR (CDCl3, 270 MHz,): delta 1.78 (3H, s, CH3CO), 3.24 (3H, s, CH3N), 4.25-4.29 (2H, m, CH2), 6.59 (IH, dd, J = 1.4, 8.0 Hz, AxH), 6.67 (IH, td, J = 1.4, 7.7 Hz, ArH), 6.83 (IH, dd, J = 1.4, 7.7 Hz, ArH), 6.88-6.92 (2H, m, AiH), 7.00 (IH, td, J = 1.6, 7.7 Hz, AiK), 7.11-7.17 (IH, m, ArH), 7.23-7.26 (2H, m, ArH), 7.31-7.34 (2H, m, ArH), 7.41- 7.44 (IH, m, ArH).13C NMR (CDCl3, 68 MHz): 26.5, 36.6 (CH3), 43.7 (CH2), 117.7, 118.7, 119.5, 125.4 (ArCH), 127.9 (ArC), 128.5, 128.9, 129.1, 129.7 (ArCH), 136.3, 139.9, 142.5, 142.8, 156.1 (ArC), 170.8 (CO). HRMS: Calcd for C22H2iClN2O2 (M+H)+ 381.1364, found (M+H)+ 381.1378.

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 77-78

65
[ 13493-47-5 ]
[ 2770-11-8 ]
[ 1158909-65-9 ]

Yield	Reaction Conditions	Operation in experiment
38%		To a solution of 2-(4-chloro-phenoxy)-phenylamine (0.128 g, 0.58 mmol) and N-(2- formyl-phenyl)-acetamide (0.19 g, 1.16 mmol) in DCE (2.6 ml) was added acetic acid(0.25 ml) and sodium triacetoxyborohydride (0.31 g, 1.45 mmol). The resulting reaction mixture was heated in a CEM microwave for 10 minutes at 140 0C. NaHCO3 was then added and the mixture was repeatedly extracted with EtOAc. The organic layers were combined, dried (MgSO4) filtered and evaporated in vacuo. The crude mixture was purified using flash chromatography (0-100% DCM in hexane) to afford the title compound as a white solid, 80 mg, 38 % yield.R.f. 0.33 (DCM), m.p. 194-196 0C,LCMS: tr = 1.36 min (95 % MeOH in H2O), m/z M-H 365.4, HPLC: ttau = 5.1 min (90 % ACN in H2O, 0.5ml/min), 98 %,1H NMR (DMSO, 400 MHz): delta 2.02 (3H, s, CH3), 4.27 (2H, d, J = 5.6 Hz, CH2), 5.95(IH, s, NH), 6.46 (IH, d, J= 8.4 Hz, ArH), 6.55 (IH, td, J= 0.8, 7.6 Hz, ArH), 6.84 (IH, dd, J = 1.6, 8.0, ArH), 6.89-6.95 (3H, m, ArH), 7.07-7.11 (IH, m, ArH), 7.16-7.22 (2H, m, ArH), 7.35-7.41 (3H, m, ArH), 9.47 (IH, br.s, NHCO). 13C NMR (DMSO, 101 MHz): 23.2 (CH3), 42.6 (CH2), 111.7, 116.0, 118.3, 120.2, 125.2,125.3, 125.6 (ArCH), 126.0 (ArC), 126.7, 126.9, 129.6 (ArCH), 133.5, 135.8, 140.5,141.6, 156.7 (ArC), 168.5 (CO).HRMS: Calcd for C21H19ClN2O2 (M+H)+ 367.1208, found (M+H)+ 367.1204.Anal, calcd for C21Hi9ClN2O2: C 68.76, H 5.22, N 7.64 %. Found: C 69.0, H 5.28, N 7.52%.

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 59

66
[ 13493-47-5 ]
[ 2770-11-8 ]
[ 1158910-26-9 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium sulfate; In dichloromethane; at 20℃; for 18h;Product distribution / selectivity;	A solution of 2-(4-chloro-phenoxy)-phenylamine (100 mg, 0.46 mmol) and 7V-(2-formyl- phenyl)-acetamide (74 mg, 0.46 mmol) in anhydrous DCM (5ml) was stirred at r.t. and to this was added MgSO4 (550 mg, 4.6 mmol) and the resulting mixture stirred for a further18h at r.t. The mixture was then filtered and the solid was washed with DCM. The filtrate was then evaporated to dryness to yield the desired product. The product was identified by NMR, as no CHO peak was visible in the 1H NMR and it had been replaced with an imine peak. The product was used crude in all following experiments.
	With triisopropoxytitanium(IV) chloride; In dichloromethane; at 20℃; for 4h;Product distribution / selectivity;	A solution of 2-(4-chloro-phenoxy)-phenylamine (100 mg, 0.46 mmol) and N-(2-formyl- phenyl)-acetamide (74 mg, 0.46 mmol) in anhydrous DCM (5ml) was stirred at r.t. and to this was added TiCl(O1Pr)3 (0.25 mL, 1 mmol). The resulting mixture was stirred for a further 4 h at room temperature. The mixture was then evaporated to dryness to yield the desired product. As in Method 1 (see above) the product could easily be identified by 1H NMR. The product was used crude in all following experiments.1H NMR (CDCl3, 270 MHz,): delta 2.03 (3H, s, CH3), 6.87-7.46 (HH, m, ArH), 8.60 (IH, s, N=CH), 8.72 (IH, d, J= 8.5 Hz, ArH). <n="97"/>13C NMR (CDCl3, 101 MHz): 24.9 (CH3), 116.7, 119.2, 119.6, 120.3 (ArCH), 120.6 (ArC), 122.5, 125.0, 127.9 (ArCH), 128.2 (ArC), 129.8, 132.7 (ArCH), 140.4, 141.7, 149.6, 156.1 (ArC), 163.4 (CH), 169.9 (CO).

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 94
[2]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 94-95

67
C₁₈H₁₄ClNO₂ [ No CAS ]
[ 2770-11-8 ]
[ 1403815-58-6 ]

Reference： [1]Medicinal Chemistry,2012,vol. 8,p. 831 - 833

68
C₁₈H₁₁ClN₂O₂ [ No CAS ]
[ 2770-11-8 ]
[ 1403815-59-7 ]

Reference： [1]Medicinal Chemistry,2012,vol. 8,p. 831 - 833

69
[ 2770-11-8 ]
[ 79-03-8 ]
[ 1621321-63-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 17h;	To a magnetically stirred solution of <strong>[2770-11-8]2-(4-chlorophenoxy)aniline</strong> (95 mg, 0.432 mmol, 76 muL) in CH2Cl2 (1.5 mL) at room temperature was added dropwise propionylchloride (48 mg, 0.518 mmol, 45 muL) followed several minutes later by ethyldiisopropylamine (0.2 mL). The reaction was stirred at room temperature for a further 17 hours, quenched with H2O (10 mL) and partitioned with CH2Cl2 (10 mL). The aqueous layer was extracted with CH2Cl2 (10 mL), and the combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified over silica gel with 0-50% ethyl acetate in cyclohexane to yield N-[2-(4-chlorophenoxy)phenyl]propanamide (109 mg, 0.395 mmol), Example 14, in 91% yield. LCMS ESI+: 276 [M+H]+, Rt 9.1 min (LCMS 01).
91%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 17h;	To a magnetically stirred solution of <strong>[2770-11-8]2-(4-chlorophenoxy)aniline</strong> (95 mg, 0.432 mmol, 76 muIota_) in CH2CI2(1 .5 mL) at room temperature was added dropwise propionylchloride (48 mg, 0.518 mmol, 45 mu) followed several minutes later by ethyldiisopropylamine (0.2 mL). The reaction was stirred at room temperature for a further 17 hours, quenched with H20 (10 mL) and partitioned with CH2CI2(10 mL). The aqueous layer was extracted with CH2CI2(10 mL), and the combined organic extracts were dried (Na2S04), filtered and concentrated in vacuo. The residue was purified over silica gel with 0-50% ethyl acetate in cyclohexane to yield N-[2-(4-chlorophenoxy)phenyl]propanamide (109 mg, 0.395 mmol), Example 14, in 91 % yield. LCMS ESI+: 276 [M+H]+, Rt 9.1 min (LCMS 01 ).
63%	With triethylamine; In toluene; at 0 - 20℃;	General procedure: To a stirred and cooled solution of <strong>[2770-11-8]2-(4-chlorophenoxy)aniline</strong> (330 mg, 1.50 mmol) and triethylamine (230 muL, 1.65 mmol) in toluene (5 mL), the appropriate acid chloride (pivaloyl chloride, 2,2-dimethylbutyryl chloride, 3-methylbutyryl chloride, propyl chloride, cyclopropanecarbonyl chloride, cyclobutanecarbonyl chloride, methyl succinyl chloride, 4-methoxybenzoyl chloride) (1.65 mmol) was added. Subsequently the reaction mixture was allowed to warm to room temperature. The progress of the reaction was monitored by TLC. After 2-9 h the reaction mixture was extracted with a saturated sodium hydrogen carbonate solution, with a hydrogen chloride solution (10%), with brine and finally with water. Afterwards the organic solution was dried over sodium sulfate and evaporated under reduced pressure. The residue was further purified by recrystallization or column chromatography over silica gel.

Reference： [1]Patent: EP2762134,2014,A1 .Location in patent: Paragraph 0102
[2]Patent: WO2014/118361,2014,A1 .Location in patent: Page/Page column 29
[3]Molecules,2016,vol. 21

70
[ 201230-82-2 ]
[ 2770-11-8 ]
[ 13210-15-6 ]

Yield	Reaction Conditions	Operation in experiment
30%		General procedure: General procedure for the preparation of xanthones from the ortho diazonium salts of diphenylethers using Pd(PPh3)4: An autoclave was charged with the diazonium salts of diaryl ethers (0.5mmol), toluene (5 mL), Pd(PPh3)4 (28 mg, 0.025 mmol) and K2CO3 (69 mg, 0.5 mmol) and catalyticTBAB (16 mg, 0.05 mmol), and the atmosphere was purged with carbon monoxide. The mixturewas stirred at 80C for 10 hours under a carbon monoxide atmosphere (0.2 MPa). Aftercompletion, the metal precipitate was filtered; the filtrate was diluted with ethyl acetate andwater. The aqueous phase was extracted with ethyl acetate twice and the combined organicphases were washed with brine and dried over MgSO4. Then solvent was evaporated undervacuum and the crude product was purified by column chromatography on silica gel, eluting witha mixture of petroleum ether and ethyl acetate to give xanthones. Yields are listed in Table 2.9H-xanthen-9-one 2a

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 6432 - 6434

71
[ 1493-27-2 ]
[ 2770-11-8 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 14060 - 14067
[2]Organic Letters,2017,vol. 19,p. 3855 - 3858
[3]European Journal of Medicinal Chemistry,2019,vol. 171,p. 195 - 208

72
[ 2770-11-8 ]
phenanthrene bicyclic anhydride [ No CAS ]
11-(2-(4-chlorophenoxy)phenyl)-9,13-diphenyl-12a,13-dihydro-9H-9,13-methanophenanthro[9,10-f]-isoindole-10,12,14-(9aH,11H)-trione [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 14060 - 14067

73
[ 2770-11-8 ]
1,4-diphenyl-1,4-epoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic anhydride [ No CAS ]
2-(2-(4-chlorophenoxy)phenyl)-4,9-diphenyl-3a,4,9,9a-tetrahydro-1H-4,9-epoxybenzo[f]isoindole-1,3(2H)-dione [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 14060 - 14067

74
[ 2770-11-8 ]
[ 1885-14-9 ]
phenyl [2-(4-chlorophenoxy)phenyl]carbamate [ No CAS ]