[ CAS No. 477312-85-9 ] {[proInfo.proName]}

Name: 477312-85-9|(S)-N-Boc-1-(3-bromophenyl)ethylamine|98%
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SKU: A708248
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Quality Control of [ 477312-85-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 477312-85-9 ]

Product Details of [ 477312-85-9 ]

CAS No. :	477312-85-9	MDL No. :	MFCD09038008
Formula :	C₁₃H₁₈BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WWNQMGYJYMXOEU-VIFPVBQESA-N
M.W :	300.19	Pubchem ID :	56971804
Synonyms :

Calculated chemistry of [ 477312-85-9 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.46
Num. rotatable bonds :	5
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	72.46
TPSA :	38.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.26
Log Po/w (XLOGP3) :	3.52
Log Po/w (WLOGP) :	3.71
Log Po/w (MLOGP) :	3.32
Log Po/w (SILICOS-IT) :	2.95
Consensus Log Po/w :	3.35

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.85
Solubility :	0.0424 mg/ml ; 0.000141 mol/l
Class :	Soluble
Log S (Ali) :	-4.01
Solubility :	0.0294 mg/ml ; 0.000098 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.62
Solubility :	0.00712 mg/ml ; 0.0000237 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.53

Safety of [ 477312-85-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P301+P312-P330	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 477312-85-9 ]

* 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.

Downstream synthetic route of [ 477312-85-9 ]

[ 477312-85-9 ] Synthesis Path-Downstream 1~60

1
[ 288-32-4 ]
[ 477312-85-9 ]
(S)-1-(3-imidazol-1-yl-phenyl)-ethylamine [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4217 - 4218

2
[ 109-01-3 ]
[ 477312-85-9 ]
[ 477313-02-3 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

3
[ 24424-99-5 ]
[ 74877-08-0 ]
[ 477312-85-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;	To a solution of [(1 S)-1-(3-bromophenyl)ethyl]amine (2g) in dry dichloromethane (20ml) and triethylamine (2.8ml) at O0C under argon was added a solution of di-te/f-butyl dicarbonate (2.62g) in dry dichloromethane (5ml) dropwise. After the addition, the reaction mixture was stirred at room temperature for two hours. The reaction mixture was washed with saturated sodium chloride (2 x 25ml) then evaporated. The residue was dissolved in dichloromethane and applied to a Biotage Si 40+M column then purified on the Biotage SP4 eluting with 0 to 50% ethyl acetate / hexane over 20CV to afford the title compound (2.89g) as a colourless oil.
	With triethylamine; In dichloromethane; at 20℃; for 2h;	To a mixture of <strong>[74877-08-0](S)-1-(3-bromophenyl)ethylamine</strong> (40.0 g, 200 mmol) and triethylamine (40.5 g, 400 mmol) in dichloromethane (400 mL) was added a solution of di-t-butyl-di-carbonate (52.4 g, 240 mmol) in dichloromethane (100 mL). The solution was stirred at room temperature for 2 h. The reaction was quenched with water (100 mL). The organic layer was washed with brine (2?250 ml), dried over magnesium sulfate and concentrated under vacuum to the title compound as white solid (61 g).
	With triethylamine; In dichloromethane; at 20℃; for 4h;	To a solution of <strong>[74877-08-0](S)-1-(3-bromo-phenyl)-ethylamine</strong> (8 g, 40 mmol) and Et3N (8.4 mL, 60 mmol) in CH2Cl2 (200 mL) was added di-tert-butyl dicarbonate (8.7 g, 40 mmol), and the reaction mixture was stirred at room temperature for 4 h. HCl 0.25 N (100 mL) was added and the two layers were separated. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuo to provide the title compound (12 g) as a white solid. [0124] 1H NMR (CDCl3, 400 MHz): delta 1.42 (m, 12 H), 4.76 (m, 3 H), 7.1-7.3 (m, 2 H), 7.36 (d, J=7.1 Hz, 1H). 7.46 (s, 1 H)

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896
[2]Patent: WO2009/50227,2009,A1 .Location in patent: Page/Page column 59
[3]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 383 - 386
[4]Patent: US2004/110765,2004,A1 .Location in patent: Page/Page column 7
[5]Patent: US2004/110754,2004,A1 .Location in patent: Page 12-13

4
homomorpholine hydrochloride [ No CAS ]
[ 477312-85-9 ]
[ 701938-93-4 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

5
[ 141-91-3 ]
[ 477312-85-9 ]
[ 477312-86-0 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

6
[ 121-43-7 ]
[ 477312-85-9 ]
C₁₅H₂₄BNO₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 363 - 366

7
[ 351019-18-6 ]
[ 477312-85-9 ]
[ 840475-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 100℃; for 18h;	To a solution of (S)-1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (2.3 g, 7.6 mmol) and 2-fluoropyridine-3-boronic acid (1 g, 7.09 mmol in ethyleneglycoldimethylether (30 mL) were added cesium carbonate (6.3 g, 19.3 mmol) and water (5 mL). Argon was bubbled into the above solution for 10 min, and Pd(PPh3)4 (372 mg, 0.32 mmol) was added. The reaction mixture was stirred at 100 C. for 18 h and then cooled down to room temperature. Ethyl acetate (100 mL) was added, the resulting solution was washed with NH4Cl (sat.) (2×100 mL), and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo, and the crude product was diluted in CH2Cl2 (30 mL) and trifluoroacetic acid (10 mL). The reaction mixture was agitated for 1 h at room temperature and concentrated in vacuo. The residue was purified by solid phase extraction (SCX cartridge, silica gel benzene sulfonic acid linked) to give the title product (1.18 g) as brown oil. 1H NMR (DMSO d6, 400 MHz): delta 1.26 (d, 3 H, J=6.6 Hz), 4.06 (q, 1 H, J=6.6 Hz), 7.28 (dd, 1H J=8.6, 3.3 Hz,), 7.4-7.45 (m, 2H), 7.5-7.55 (m, 1H), 7.71 (s, 1H), 8.27 (dd, 1H J=8.6, 2.8 Hz,), 8.54 (d, 1H J=2.5 Hz).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 363 - 366
[2]Patent: US2004/106621,2004,A1 .Location in patent: Page 10

8
[ 477312-85-9 ]
[ 477312-98-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 363 - 366
[2]Patent: US2004/106621,2004,A1

9
[ 477312-85-9 ]
[ 477312-96-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 363 - 366
[2]Patent: US2004/106621,2004,A1

10
[ 477312-85-9 ]
[ 477312-94-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 363 - 366

11
[ 477312-85-9 ]
[ 840475-09-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 363 - 366
[2]Patent: US2004/106621,2004,A1

12
[ 477312-85-9 ]
[ 840475-08-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 363 - 366
[2]Patent: US2004/106621,2004,A1

13
[ 477312-85-9 ]
[ 477312-91-7 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of (S)-1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (5 g, 16.6 mmol) in THF (100 mL) at -78 C. was added methyllithium (11.8 mL, 1.4M in Et2O, 16.6 mmol), and the reaction mixture was stirred at -78 C. for 5 min. tert-Butyllithium (19.6 mL, 1.7 M in pentane, 33.4 mmol) was added, the reaction mixture was stirred for 5 min, and trimethylborate (2.82 mL, 24.9 mmol) was added rapidly. The reaction mixture was agitated at -78 C. for 1 h, NH4Cl (sat.) (100 mL) was added, and the resulting solution was allowed to reach room temperature. The reaction mixture was extracted with ethyl acetate (3×100 mL), the organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography (30% EtOAC/Hex.) to provide the title compound (2.7 g) as a white solid. [0085] 1H NMR (DMSO d6, 400 MHz): delta 1.2-1.4 (m, 12 H), 4.6-4.7 (m, 3 H), 7.2-7.4 (m, 2 H), 7.6-7.8 (m, 2 H).
		(S)-1-(3-Bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (5 g, 16.6 mmol) were added in THF (100 mL)and cooled to -78 C., methyllithium (11.8 mL, 1.4M in Et2O, 16.6 mmol) was added, and the reaction mixture was stirred for 5 min. tert-Butyllithium (19.6 mL, 1.7 M in pentane, 33.4 mmol) was added, the reaction mixture was stirred for 5 min, and trimethylborate (2.82 mL, 24.9 mmol) was added rapidly. The reaction mixture was agitated for 1 h, NH4Cl (sat.) (100 mL) was added, and the resulting solution was allowed to reach 23 C. The reaction mixture was extracted with ethyl acetate (3×100 mL), the organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography (30% EtOAC/Hex.) to provide the title compound (2.7 g) as white solid. [0145] 1H NMR (DMSO d6, 400 MHz): delta 1.2-1.4 (m, 12 H), 4.6-4.7 (m, 3 H), 7.2-7.4 (m, 2 H), 7.6-7.8 (m, 2 H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 363 - 366
[2]Patent: US2004/106621,2004,A1 .Location in patent: Page 9
[3]Patent: US2004/110754,2004,A1 .Location in patent: Page 15

14
[ 477312-85-9 ]
(S)-3-(2-Fluoro-phenyl)-N-[1-(3-pyridin-2-yl-phenyl)-ethyl]-acrylamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 363 - 366

15
[ 477312-85-9 ]
(S)-3-(2-fluoro-phenyl)-N-[1-(3-pyrazin-2-yl-phenyl)ethyl]acrylamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 363 - 366

16
[ 477312-85-9 ]
(S)-3-(2-Fluoro-phenyl)-N-{1-[3-(6-fluoro-pyridin-3-yl)-phenyl]ethyl}-acrylamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 363 - 366

17
[ 477312-85-9 ]
[ 477313-03-4 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

18
[ 477312-85-9 ]
(E)-N-[(S)-1-(3-[1,4]Oxazepan-4-yl-phenyl)-ethyl]-3-phenyl-acrylamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

19
[ 477312-85-9 ]
(E)-3-(2-Fluoro-phenyl)-N-{(S)-1-[3-(4-methyl-piperazin-1-yl)-phenyl]-ethyl}-acrylamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

20
[ 477312-85-9 ]
(S)-N-{1-[3-(2,6-cis-dimethylmorpholin-4-yl)phenyl]ethyl}-3-(2-fluorophenyl)acrylamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

21
[ 477312-85-9 ]
(S)-N-{1-[3-(2,6-cis-dimethylmorpholin-4-yl)phenyl]ethyl}-3-(4-fluorophenyl)acrylamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

22
[ 477312-85-9 ]
(S)-1-(3-[1,4]-oxazepan-4-yl-phenyl)ethylamine dihydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

23
[ 477312-85-9 ]
(S)-1-[3-(cis-2,6-dimethylmorpholin-4-yl)phenyl]ethylamine dihydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

24
(R)-(+)-3-(dimethylamino)pyrrolidine [ No CAS ]
[ 477312-85-9 ]
[ 701914-07-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); In 1,2-dimethoxyethane; for 16h;Heating / reflux;	A mixture of (S )[1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (6 g), (3R)-3-(dimethylamino)-pyrrolidine (4.56 g), Pd2(dba)3 (1.83 g), di-t-butyl-biphenylphosphine (600 mg), K3PO4 (8.48 g) in DME (40 mL) was stirred at reflux for 16 h. The reaction mixture was cooled down to room temperature, diluted with methylene chloride, and filtered. The filtrated was evaporated in vacuo, and the crude product was purified by Flash Chromatography using Biotage eluting with 20% MeOH in ethyl acetate to give the title compound (1.8 g) as an oil. MS (M+H)+ 334.

Reference： [1]Patent: US2004/110754,2004,A1 .Location in patent: Page 13

25
[ 1692-25-7 ]
[ 477312-85-9 ]
[ 697804-10-7 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of (S)-1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (1.5 g, 5 mmol) and pyridine-3-boronic acid (921 mg, 7.5 mmol) in ethyleneglycoldimethylether (25 mL) in a sealed tube were added cesium carbonate (3.25 g, 10 mmol) and water (10 mL). Argon was bubbled into the above mixture for 10 min, and Pd(PPh3)4 (289 mg, 0.25 mmol) was added. The reaction mixture was stirred at 100 C. for 18 h and cooled down to room temperature. Ethyl acetate (100 mL) was added, the resulting solution was washed with NH4Cl (sat.) (2×100 mL), the organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated in vacuo. The crude product was diluted in CH2Cl2 (30 mL) and trifluoroacetic acid (10 mL). The reaction mixture was agitated for 1 h and concentrated in vacuo. The residue was purified by solid phase extraction (SCX cartridge, silca gel benzene sulfonic acid linked) to give the title product (424 mg) as a yellow oil. [0142] 1H NMR (CDCl3, 400 MHz): delta 1.26 (d, 3 H, J=6.6 Hz), 3.90 (q, 1 H, J=6.6 Hz), 6.87 ( dd, 1H, J=4.8, 7.8 Hz), 7.2-7.35 (m, 3H), 7.45-7.55 (m, 2H), 8.64 (s, 1H),9.11 (s, 1H).

Reference： [1]Patent: US2004/110754,2004,A1 .Location in patent: Page 14-15

26
[ 351019-18-6 ]
[ 477312-85-9 ]
[ 477312-94-0 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of (s)-1-(3-Bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (2.3 g, 7.6 mmol) and 2-fluoropyridine-3-boronic acid (1 g, 7.09 mmol in ethyleneglycoldimethylether (30 mL) were added cesium carbonate (6.3 g, 19.3 mmol) and water (5 mL. Argon was bubbled into the above solution for 10 min, and Pd(PPh3)4 (372 mg, 0.32 mmol) was added. The reaction mixture was stirred at 100 C. for 18 h and then cooled down to room temperature. Ethyl acetate (100 mL) was added, the resulting solution was washed with NH4Cl (sat.) (2×100 mL), and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the crude product was diluted in CH2Cl2 (30 mL) and trifluoroacetic acid (10 mL). The reaction mixture was agitated for 1 h and concentrated in vacuo. The residue was purified by solid phase extraction (SCX cartridge, silca gel benzene sulfonic acid linked) to give the title product (1.18 g) as brown oil. [0150] 1H NMR (DMSO d6, 400 MHz): delta 1.26 (d, 3 H, J=6.6 Hz), 4.06 (q, 1 H, J=6.6 Hz), 7.28 (dd, 1H J=8.6, 3.3 Hz,), 7.4-7.45 (m, 2H), 7.5-7.55 (m, 1H), 7.71 (s, 1H), 8.27 (dd, 1H J=8.6, 2.8 Hz,), 8.54 (d, 1H J=2.5 Hz,).

Reference： [1]Patent: US2004/110754,2004,A1 .Location in patent: Page 16

27
[ 34803-66-2 ]
[ 477312-85-9 ]
(S)-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); biphenyl-4-yl(di-tert-butylphosphine); In ethyleneglycol dimethyl ether; for 4h;Heating / reflux;	A mixture of <strong>[477312-85-9](S)-[1-(3-bromophenyl)ethyl]carbamic acid tert-butyl ester</strong> (5.0 g, 16.7 mmol), 1-pyridin-2-ylpiperazine (10.9 g, 67 mmol), Pd2(dba)3 (1.55 g, 10 mol %), di-t-butyl-biphenylphosphine (0.51 g, 10 mol %), potassium phosphate (7.2 g, 34 mmol) in ethyleneglycol dimethyl ether (40 mL) was refluxed for 4 h. After cooling to room temperature, the reaction mixture was diluted with dichloromethane (100 mL) and the precipitate was filtered off. The filtrate was concentrated under vacuum. The crude product was purified by flash chromatography over silica with ethyl acetate/hexanes (1:2) to provide the title compound as an oil (4.1 g, 64% yield). MS (M+H)+ 383.

Reference： [1]Patent: US2004/110765,2004,A1 .Location in patent: Page/Page column 7

28
[ 288-32-4 ]
[ 477312-85-9 ]
C₁₆H₂₁N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,10-Phenanthroline; copper(II) trifluoromethanesulfonate; caesium carbonate; 1,5-diphenyl-1,4-pentadiene-3-one; benzene; In xylenes; at 110℃; for 18h;	A mixture of (S)-1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (500 mg, 1.66 mmol), imidazole (170 mg, 2.5 mmol), copper (II) triflate benzene complex (83 mg, 0.16 mmole), 1-10 phenantroline ( 300 mg, 1.66 mmole), dibenzilideneacetone (37 mg, 0.16 mmole), and cesium carbonate (595 mg, 1.86 mmole) was suspended in xylenes (1 mL) in a sealed tube. The reaction mixture was heated at 110 C. for 18 h in an oil bath and then cooled down to room temperature. Ethyl acetate (20 mL) was added, the resulting solution was washed with water (2×20 mL), and the combined organic layers were dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo, and the crude product was dissolved in CH2Cl2 (8 mL) and trifluoroacetic acid (2 mL). The reaction mixture was stirred at room temperature for 1 h and concentrated in vacuo. The residue was purified by preparative HPLC ( NH4OAc) to give the title product (75 mg, 24% yield). 1H NMR (CDCl3, 400 MHz): delta 1.46 (d, 3 H, J=7.1 Hz), 4.79 (s, 1 H), 5.19 (s, 1 H), 7.25-7.6 (m, 6H), 9.09 (s, 1H).

Reference： [1]Patent: US2004/106621,2004,A1 .Location in patent: Page 13; 14

29
[ 1692-25-7 ]
[ 477312-85-9 ]
C₁₈H₂₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 100℃; for 18h;	To a solution of (S)-1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (1.5 g, 5 mmol) and pyridine-3-boronic acid (921 mg, 7.5 mmol) in ethyleneglycoldimethylether (25 mL) in a sealed tube were added cesium carbonate (3.25 g, 10 mmol) and water (10 mL). Argon was bubbled into the above mixture for 10 min, and Pd(PPh3)4 (289 mg, 0.25 mmol) was added. The reaction mixture was stirred at 100 C. for 18 h and cooled down to room temperature. Ethyl acetate (100 mL) was added, the resulting solution was washed with NH4Cl (sat.) (2×100 mL), the organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuo. The crude product was diluted in CH2Cl2 (30 mL) and trifluoroacetic acid (10 mL). The reaction mixture was agitated for 1 h and concentrated in vacuo. The residue was purified by solid phase extraction (SCX cartridge, silca gel benzene sulfonic acid linked) to give the title product (424 mg) as a yellow oil. 1H NMR (CDCl3, 400 MHz): delta 1.26 (d, 3 H, J=6.6 Hz), 3.90 (q, 1 H, J=6.6 Hz), 6.87 ( dd, 1H, J=4.8, 7.8 Hz), 7.2-7.35 (m, 3H), 7.45-7.55 (m, 2H), 8.64 (s, 1H), 9.11 (s, 1H ).

Reference： [1]Patent: US2004/106621,2004,A1 .Location in patent: Page 8

30
[ 24424-99-5 ]
[ 477312-85-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃; for 4h;	To a solution of (S)-1-(3-bromo-phenyl)-ethylamine (8 g, 40 mmol) and Et3N (8.4 mL, 60 mmol) in CH2Cl2 (200 mL) was added di-tert-butyl dicarbonate (8.7 g, 40 mmol), and the reaction mixture was stirred at room temperature for 4 h. HCl 0.25 N (100 mL) was added and the two layers were separated. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuo to provide the title compound (12 g) as a white solid. 1H NMR (CDCl3, 400 MHz): delta 1.42 (m, 12 H), 4.76 (m, 3 H), 7.1-7.3 (m, 2 H), 7.36 (d, J=7.1 Hz, 1H). 7.46 (s, 1 H)

Reference： [1]Patent: US2004/106621,2004,A1 .Location in patent: Page 8

31
[ 1692-15-5 ]
[ 477312-85-9 ]
C₁₈H₂₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 100℃; for 18h;	To a solution of (S)-1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (1.5 g, 5 mmol) and pyridine-4-boronic acid (921 mg, 7.5 mmol) in ethyleneglycoldimethylether (25 mL) in a sealed tube were added cesium carbonate (3.25 g, 10 mmol) and water (10 mL). Argon was bubbled for 10 min, and Pd(PPh3)4 (289 mg, 0.25 mmol) was added. The reaction mixture was stirred at 100 C. for 18 h and cooled down to room temperature. Ethyl acetate (100 mL) was added, the resulting solution was washed with NH4Cl (sat.) (2×100 mL), and the organic layer was dried over anhydrous magnesium sulfate, filtered. The filtrate was concentrated in vacuo, and the residue was dissolved in CH2Cl2 (30 mL) and trifluoroacetic acid (10 mL). The reaction mixture was stirred at room temperature for 1 h and concentrated in vacuo. The residue was purified by solid phase extraction (SCX cartridge, silca gel benzene sulfonic acid linked) to give the title product (424 mg, 43% yield) as yellow oil. 1H NMR (DMSO d6, 400 MHz): delta 1.28 (d, 3 H, J=6.6 Hz), 4.05 (q, 1 H, J=6.6 Hz), 7.4-7.45 (m, 2H), 7.55-7.65 (m, 2H), 7.67-7.72 (m, 2H), 7.79 (s, 1H), 8.60-8.65 (m, 1H).

Reference： [1]Patent: US2004/106621,2004,A1 .Location in patent: Page 8; 9

32
[ 16114-47-9 ]
[ 477312-85-9 ]
C₁₈H₂₄N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 100℃; for 18h;	To a solution of (S)-1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (155 mg, 0.52 mmol) and 3,5-bimethyl-isoxazole-3-boronic acid (73 mg, 0.52 mmol) in ethyleneglycoldimethylether (5 mL) in a sealed tube were added cesium carbonate (508 mg, 1.56 mmol) and water (1 mL). Argon was bubbled into the solution for 10 min, Pd(PPh3)4 (30 mg, 0.025 mmol) was added, and the reaction mixture was stirred at 100 C. for 18 h. The reaction mixture was cooled down to room temperature, Ethyl acetate (20 mL) was added, and the resulting solution was washed with water (2×20 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuo. The crude product was diluted in CH2Cl2 (8 mL) and trifluoroacetic acid (2 mL), and the reaction mixture was stirred at room temperature for 1 h and concentrated in vacuo. The residue was purified by solid phase extraction (SCX cartridge, silica gel benzene sulfonic acid linked) to give the title product (57 mg, 50% yield) as a yellow oil. 1H NMR (acetone d6, 400 MHz): delta 1.66 (d, 3 H, J=6.6 Hz), 2.47 (s, 3H), 2.64 (s, 3H), 4.47 (q, 1 H, J=6.8 Hz), 7.52 (m, 1H), 7.6-7.75 (m, 3H).

Reference： [1]Patent: US2004/106621,2004,A1 .Location in patent: Page 11; 12

33
[ 292638-85-8 ]
[ 477312-85-9 ]
[ 881206-59-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tri-tert-butyl phosphine; N-Methyldicyclohexylamine;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 80℃; for 3h;	(S)-tert-Butyl 1-(3-bromophenyl)ethylcarbamate (7.4 g, 24.5 mmol), methacrylate (4.21 g, 49 mmol), palladium dibenzylidene acetone (1.35 g, 1.47 mmol), tri-tert-butyl phosphine (594 mg, 3.0 mmol), dicyclohexyl methylamine (5.75 g, 29.4 mmol), and 1,4-dioxane (45 mL) were mixed under argon atmosphere in a 250 mL roundbottom flask equipped with a stir bar. The mixture was heated to 80 C. for 3 h, cooled to RT, partitioned between water and ethyl acetate, the layers separated, and the aqueous layer extracted with ethyl acetate twice. The combined extracts were washed with brine, dried (MgSO4), filtered, concentrated under vacuum, and purified by flash column chromatography to give (S,E)-methyl 3-(3-(1-(tert-butoxycarbonyl)ethyl)phenyl)acrylate as an oil (7.0 g). NMR (CDCl3) delta: 7.68 (d, J=16.0 Hz, 1H), 7.42 (m, 2H), 7.34 (m, 2H), 6.44 (d, J=16.0 Hz, 1H), 4.81 (br m, 2H), 3.81 (s, 3H), 1.44 (s, 9H), 1.44 (br d, 3H).

Reference： [1]Patent: US2006/69110,2006,A1 .Location in patent: Page/Page column 17

34
[ 110-91-8 ]
[ 477312-85-9 ]
[ 477312-35-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); johnphos; at 80℃; for 21h;	A mixture of 1 ,1 -dimethylethyl [(1 S)-1-(3-bromophenyl)ethyl]carbamate (1.5g), morpholine (10ml), tris(dibenzylideneacetone)dipalladium(0) (229mg), 2-(di-tert- butylphosphino)-biphenyl (298mg) and potassium phosphate (1.485g) was heated at 8O0C under argon for twenty one hours. The reaction mixture was cooled, diluted with <n="61"/>dichloromethane (50ml), and washed with water (10ml). The aqueous layer was extracted with dichloromethane (2 x 15ml), and the combined organic layers were evaporated. The residue was dissolved in dichloromethane and applied to a Biotage Si 40+M column then purified on the Biotage SP4 eluting with 0 to 30% ethyl acetate / hexane over 10CV then 30% ethyl acetate / hexane over 5CV to afford the title compound (627mg) as a yellow oil.MS (ES) Ci7H26N2O3 requires 306; found 307 [M+H]+

Reference： [1]Patent: WO2009/50227,2009,A1 .Location in patent: Page/Page column 59-60

35
[ 68-12-2 ]
[ 477312-85-9 ]
[ 697804-15-2 ]

Yield	Reaction Conditions	Operation in experiment
96%		To a solution of (S)-1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (2 g, 6.66 mmol) in THF (20 mL) at -78 C. was added methyllithium (4.72 mL, 1.4M in Et2O, 6.66 mmol), and the reaction mixture was stirred at -78 C. for 5 min. tert-Butyllithium (7.76 mL, 1.7M in pentane, 13.32 mmol) was added, and the reaction mixture was stirred at -78 C. for 15 min. [0114] Dimethylformamide (1.7 mL, 13.32 mmol) was added rapidly, and the reaction mixture was warmed slowly to room temperature over a period of 1 h. NH4Cl (sat.) (100 mL) was added, the resulting mixture was extracted with ethyl acetate (3×100 mL), and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo, and the filtrated was evaporated in vacuo to give the title compound (1.6 g, 96% yield) as yellow crystals. 1H NMR (DMSO d6, 400 MHz): delta 1.41 (m, 9 H), 1.46 (d, 3H J=6.6 Hz), 4.89 (s, 1 H), 7.58 (d, 1H, J=7.3 Hz), 7.76 (d, 1H, J=7.6 Hz), 7.82 (s, 1H), 7.96 (d, 1H, J=-7.6 Hz), 10.01 (s, 1H).

Reference： [1]Patent: US2004/106621,2004,A1 .Location in patent: Page 12

36
[ 14267-92-6 ]
[ 477312-85-9 ]
C₁₈H₂₄ClNO₂ [ No CAS ]

Reference： [1]Synlett,2010,p. 1544 - 1548

37
[ 73183-34-3 ]
[ 477312-85-9 ]
[ 887254-65-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 383 - 386

38
[ 31469-15-5 ]
[ 477312-85-9 ]
[ 1415502-60-1 ]

Yield	Reaction Conditions	Operation in experiment
281 mg	With bis[tris( 1,1-dimethylethyl)phosphine]-palladium; zinc(II) fluoride; In N,N-dimethyl-formamide; at 80 - 100℃; for 72h;	Preparation Example 193 A mixture of 1 g of tert-butyl[(1S)-1-(3-bromophenyl)ethyl]carbamate, 18 mg of bis(tri-tert-butylphosphine)palladium (0), 180 mg of zinc fluoride, 1 ml of [(1-methoxy-2-methylpropa-1-en-1-yl)oxy](trimethyl)silane, and 10 ml of DMF was stirred at 80 C. overnight and at 100 C. for 5 hours. 25 mg of bis(tri-tert-butylphosphine)palladium (0) and 0.34 ml of [(1-methoxy-2-methylpropa-1-en-1-yl)oxy](trimethyl)silane were added thereto, followed by stirring at 80 C. for 3 days. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 281 mg of methyl 2-(3-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}phenyl)-2-methylpropanoate.

Reference： [1]Patent: US2014/88080,2014,A1 .Location in patent: Paragraph 0366

39
[ 67-56-1 ]
[ 201230-82-2 ]
[ 477312-85-9 ]
[ 1415502-26-9 ]

Yield	Reaction Conditions	Operation in experiment
577 mg	With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 80℃;	Preparation Example 165 To 820 mg of tert-butyl[(1S)-1-(3-bromophenyl)ethyl]carbamate were added 113 mg of 1,3-bis(diphenylphosphino)propane, 62 mg of palladium acetate, 0.84 ml of triethylamine, 8 ml of DMF, and 12 ml of methanol, followed by stirring at room temperature for 1 hour. While stirring at room temperature, carbon monooxide was intaken for 10 minutes, followed by stirring at 80 C. overnight under a carbon monooxide atmosphere. 113 mg of 1,3-bis(diphenylphosphino)propane and 62 mg of palladium acetate were added thereto, followed by stirring at 80 C. overnight. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 577 mg of methyl 3-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}benzoate.

Reference： [1]Patent: US2014/88080,2014,A1 .Location in patent: Paragraph 0339

40
[ 477312-85-9 ]
(S)-1-[3-(4-Pyridin-2-ylpiperazin-1-yl)phenyl]ethylamine [ No CAS ]

Reference： [1]Patent: US2004/110765,2004,A1

41
[ 477312-85-9 ]
(S)-3-(4-fluorophenyl)-N-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}-acrylamide [ No CAS ]

Reference： [1]Patent: US2004/110765,2004,A1

42
[ 477312-85-9 ]
[ 697804-10-7 ]