[ CAS No. 185619-66-3 ] {[proInfo.proName]}

Name: 185619-66-3|tert-Butyl (3-ethynylphenyl)carbamate|97%
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Quality Control of [ 185619-66-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 185619-66-3 ]

Product Details of [ 185619-66-3 ]

CAS No. :	185619-66-3	MDL No. :	MFCD14585306
Formula :	C₁₃H₁₅NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OVWBYRQRBCBWDM-UHFFFAOYSA-N
M.W :	217.26	Pubchem ID :	11275982
Synonyms :

Calculated chemistry of [ 185619-66-3 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.31
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	64.62
TPSA :	38.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.38 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.85
Log Po/w (XLOGP3) :	3.16
Log Po/w (WLOGP) :	2.9
Log Po/w (MLOGP) :	2.84
Log Po/w (SILICOS-IT) :	2.38
Consensus Log Po/w :	2.83

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.19
Solubility :	0.14 mg/ml ; 0.000644 mol/l
Class :	Soluble
Log S (Ali) :	-3.64
Solubility :	0.0503 mg/ml ; 0.000232 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.44
Solubility :	0.0792 mg/ml ; 0.000365 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.31

Safety of [ 185619-66-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 185619-66-3 ]

* 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 [ 185619-66-3 ]
Downstream synthetic route of [ 185619-66-3 ]

[ 185619-66-3 ] Synthesis Path-Upstream 1~7

1
[ 24424-99-5 ]
[ 54060-30-9 ]
[ 185619-66-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: at 70℃; Stage #2: at 20℃; for 1 h;	Step a) (3-Ethynyl-phenyl)-carbamic acid tert-butyl ester A solution of 3-ethynyl-phenylamine (25.0 g, 213 mmol) and di-tert-butyldicarbonate (93.1 g, 427 mmol) in THF (427 mL) was heated at 70° C. overnight. The reaction was cooled to room temperature and then 3-dimethylamino-1-propylamine (32.1 g, 320 mmol) was added and allowed to stir at room temperature for 1 h. The reaction was concentrated and taken in diethyl ether, washed with 1N HCl, brine, sodium bicarbonate, brine and dried over sodium sulfate and concentrated in vacuo to provide the title compound (45.0 g, 97percent), characterized by NMR and mass spectral analyses.
92%	for 48 h;	3-aminophenylacetylene (10.5 mL) and di-tertbutyldicarbonate (44.0 g) in THF (250 mL) were stirred for 48 hours, concentrated in vacuo, dissolved in DCM, washed with water and concentrated in vacuo. Purification by flash chromatography on silica using 0-50percent DCM in isohexane as eluent gave the title compound as a yellow oil (20.0 g, 92percent); 'HNMR (CDC13) 1.52 (s, 9H), 3.04 (s, 1H), 6.45 (s, br, 1H), 7.15 (d, 1H), 7.23 (t, 1H), 7.35 (d, 1H), 7.52 (s, 1H) ; MS m/e (M-CH3) H+ 203.
90%	Reflux	Di-tert-butyl dicarbonate(123 ml,531 mmol)was added to a stirred solution of 3-ethynylaniline(56.6 g,483 mmol)in THF(300 mL). The mixture was heated to reflux for overnight. Themixture was then cooled to ambient temperature and taken up in ethyl acetate(500 mL)and washedsequentia11y with IN aqueous HCl(200 mL),saturated aqueous Na2C03(200 mL)and brine(200 mL).The organic layer was dried over Na2S04,concentrated in vacuo,and purified by silica gel columnchromatography(eluted with 15percent EtOac/PE)to give tert-butyl (3-ethynylphenyl)carbamate(94 g,435mmol,90percent yield). LCMS(Method f,Table 7)Rt=l.80 min; MS m/z = 162 [M-t-Bu+H+].

72%

With triethylamine In tetrahydrofuran at 55℃;

Example 459(S)-tert-butyl (3-[5-([methyl(oxo)phenyl-λ⁶-sulfanylidene]amino}carbonyl)pyridin-3- yl] ethynyl} phenyl)carbamate.Step 1 tert-butyl 3-ethynylphenylcarbamateA dry 25mL flask was charged with 3-ethynyl-phenylamine (0.100 g, 0.855 mmol) and THF (5 mL) was added. Di-tert-butyl dicarbonate (0.242 g, 1.11 mmol) was added to the THF solution followed by NEt₃ (0.23mL, 1.71 mmol). The mixture was allowed to stir at 55 ⁰C after which it was cooled to room temperature and extracted twice with EtOAc (-10 mL), water (-10 mL) and saturated aqueous NaHCO₃. The combined organic extracts were dried over anhydrous Na₂SO₄(S) and then concentrated to give the title compound (0.13 g, 0.67 mmol, 72percent).

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 20, p. 4232 - 4235
[2] Patent: US2009/48320, 2009, A1, . Location in patent: Page/Page column 39-40
[3] Patent: WO2005/60970, 2005, A1, . Location in patent: Page/Page column 148
[4] Patent: WO2017/210471, 2017, A1, . Location in patent: Paragraph 001146; 001147
[5] Patent: WO2008/61236, 2008, A2, . Location in patent: Page/Page column 71
[6] Patent: US2004/167188, 2004, A1,
[7] Journal of Medicinal Chemistry, 2008, vol. 51, # 15, p. 4370 - 4373
[8] Patent: US2004/214870, 2004, A1, . Location in patent: Page 19
[9] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 678 - 688

2
[ 24424-99-5 ]
[ 185619-66-3 ]

Reference： [1] Tetrahedron, 1998, vol. 54, # 33, p. 9823 - 9836
[2] Chemical Communications, 1996, # 23, p. 2647 - 2648
[3] Chemical Communications, 2015, vol. 51, # 25, p. 5242 - 5245
[4] Chemical Communications, 2018, vol. 54, # 70, p. 9765 - 9768

3
[ 143390-49-2 ]
[ 185619-66-3 ]

Reference： [1] Tetrahedron, 1998, vol. 54, # 33, p. 9823 - 9836
[2] Chemical Communications, 1996, # 23, p. 2647 - 2648

4
[ 54060-30-9 ]
[ 24608-52-4 ]
[ 185619-66-3 ]

Reference： [1] Journal of Organic Chemistry, 2017, vol. 82, # 15, p. 8282 - 8289

5
[ 24424-99-5 ]
[ 591-19-5 ]
[ 1066-54-2 ]
[ 185619-66-3 ]

Reference： [1] New Journal of Chemistry, 2017, vol. 41, # 22, p. 13391 - 13398

6
[ 25216-74-4 ]
[ 185619-66-3 ]

Reference： [1] Chemical Communications, 2015, vol. 51, # 25, p. 5242 - 5245
[2] Chemical Communications, 2018, vol. 54, # 70, p. 9765 - 9768

7
[ 591-19-5 ]
[ 185619-66-3 ]

Reference： [1] Chemical Communications, 2015, vol. 51, # 25, p. 5242 - 5245
[2] Chemical Communications, 2018, vol. 54, # 70, p. 9765 - 9768

[ 185619-66-3 ] Synthesis Path-Downstream 1~76

1
[ 185619-66-3 ]
[ 182158-34-5 ]
{3-[(1E,3E,5E)-6-(2-Hydroxy-5-oxo-cyclopent-1-enylcarbamoyl)-hexa-1,3,5-trienyl]-phenyl}-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Chemical Communications,1996,p. 2647 - 2648

2
tert-butyl (3-((trimethylsilyl)ethynyl)phenyl)carbamate [ No CAS ]
[ 185619-66-3 ]

Reference： [1]Tetrahedron,1998,vol. 54,p. 9823 - 9836
[2]Chemistry - A European Journal,2018,vol. 24,p. 13270 - 13277
[3]Chemical Communications,2015,vol. 51,p. 5242 - 5245
[4]Chemical Communications,2018,vol. 54,p. 9765 - 9768
[5]Chemical Communications,1996,p. 2647 - 2648

3
[ 585-76-2 ]
[ 185619-66-3 ]
3-(3'-aminophenylethynyl)benzamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 6431 - 6434

4
[ 185619-66-3 ]
[ 618-51-9 ]
3-(3'-aminophenylethynyl)benzamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 6431 - 6434

5
[ 24424-99-5 ]
[ 54060-30-9 ]
[ 185619-66-3 ]

Yield	Reaction Conditions	Operation in experiment
97%		Step a) (3-Ethynyl-phenyl)-carbamic acid tert-butyl ester A solution of 3-ethynyl-phenylamine (25.0 g, 213 mmol) and di-tert-butyldicarbonate (93.1 g, 427 mmol) in THF (427 mL) was heated at 70 C. overnight. The reaction was cooled to room temperature and then 3-dimethylamino-1-propylamine (32.1 g, 320 mmol) was added and allowed to stir at room temperature for 1 h. The reaction was concentrated and taken in diethyl ether, washed with 1N HCl, brine, sodium bicarbonate, brine and dried over sodium sulfate and concentrated in vacuo to provide the title compound (45.0 g, 97%), characterized by NMR and mass spectral analyses.
92%	In tetrahydrofuran; for 48h;	3-aminophenylacetylene (10.5 mL) and di-tertbutyldicarbonate (44.0 g) in THF (250 mL) were stirred for 48 hours, concentrated in vacuo, dissolved in DCM, washed with water and concentrated in vacuo. Purification by flash chromatography on silica using 0-50% DCM in isohexane as eluent gave the title compound as a yellow oil (20.0 g, 92%); 'HNMR (CDC13) 1.52 (s, 9H), 3.04 (s, 1H), 6.45 (s, br, 1H), 7.15 (d, 1H), 7.23 (t, 1H), 7.35 (d, 1H), 7.52 (s, 1H) ; MS m/e (M-CH3) H+ 203.
90%	In tetrahydrofuran;Reflux;	Di-tert-butyl dicarbonate(123 ml,531 mmol)was added to a stirred solution of 3-ethynylaniline(56.6 g,483 mmol)in THF(300 mL). The mixture was heated to reflux for overnight. Themixture was then cooled to ambient temperature and taken up in ethyl acetate(500 mL)and washedsequentia11y with IN aqueous HCl(200 mL),saturated aqueous Na2C03(200 mL)and brine(200 mL).The organic layer was dried over Na2S04,concentrated in vacuo,and purified by silica gel columnchromatography(eluted with 15% EtOac/PE)to give tert-butyl (3-ethynylphenyl)carbamate(94 g,435mmol,90% yield). LCMS(Method f,Table 7)Rt=l.80 min; MS m/z = 162 [M-t-Bu+H+].

72%	With triethylamine; In tetrahydrofuran; at 55℃;	Example 459(S)-tert-butyl (3-[5-([methyl(oxo)phenyl-lambda6-sulfanylidene]amino}carbonyl)pyridin-3- yl] ethynyl} phenyl)carbamate.Step 1 tert-butyl 3-ethynylphenylcarbamateA dry 25mL flask was charged with 3-ethynyl-phenylamine (0.100 g, 0.855 mmol) and THF (5 mL) was added. Di-tert-butyl dicarbonate (0.242 g, 1.11 mmol) was added to the THF solution followed by NEt3 (0.23mL, 1.71 mmol). The mixture was allowed to stir at 55 0C after which it was cooled to room temperature and extracted twice with EtOAc (-10 mL), water (-10 mL) and saturated aqueous NaHCO3. The combined organic extracts were dried over anhydrous Na2SO4(S) and then concentrated to give the title compound (0.13 g, 0.67 mmol, 72%).
	In tetrahydrofuran; ethyl acetate;	Example 4A (3-ethynyl-phenyl)-carbamic Acid Tert-Butyl Ester To 3-ethynyl-phenylamine (5.66 g, 0.0483 mole) in THF (90 mL) was added Boc2O (6.07 g, 0.0278 mole). The mixture was heated to reflux for 16 hours, cooled to ambient temperature, taken up in ethyl acetate (200 mL) and washed with aqueous 1N HCl (3*50 mL), saturated Na2CO3 and brine. The organic layer was dried over anhydrous Na2SO4, filtered, concentrated in vacuo and purified by flash chromatography (15% ethyl acetate/Hexane) to provide the titled compound (10.46 g).
	In tetrahydrofuran; for 16h;Heating / reflux;	To 3-ethynyl-phenylamine (5.66 g, 0.0483 mole) in TBF (90 mL) was added Boc 2O (6.07 g, 0.0278 mole). The mixture was heated to reflux for 16 hours, cooled to ambient temperature, taken up in ethyl acetate (200 mL) and washed with aqueous 1N HCl (3 50 mL), saturated Na 2CO 3 and brine. The organic layer was dried over anhydrous Na 2SO 4, filtered, concentrated in vacuo and purified by flash chromatography (15% ethyl acetate/Hexane) to provide the titled compound (10.46 g).

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4232 - 4235
[2]Patent: US2009/48320,2009,A1 .Location in patent: Page/Page column 39-40
[3]Patent: WO2005/60970,2005,A1 .Location in patent: Page/Page column 148
[4]Patent: WO2017/210471,2017,A1 .Location in patent: Paragraph 001146; 001147
[5]Patent: WO2008/61236,2008,A2 .Location in patent: Page/Page column 71
[6]Patent: US2004/167188,2004,A1
[7]Journal of Medicinal Chemistry,2008,vol. 51,p. 4370 - 4373
[8]Patent: US2004/214870,2004,A1 .Location in patent: Page 19
[9]Journal of Medicinal Chemistry,2010,vol. 53,p. 678 - 688

6
[ 14337-43-0 ]
[ 185619-66-3 ]
[ 745078-83-5 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4232 - 4235
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 4370 - 4373
[3]Journal of Medicinal Chemistry,2010,vol. 53,p. 678 - 688
[4]Patent: WO2017/40564,2017,A1 .Location in patent: Paragraph 0094

7
[ 185619-66-3 ]
[ 745078-84-6 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4232 - 4235

8
[ 185619-66-3 ]
5-(3-butyrylamino-phenyl)-isoxazole-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4232 - 4235

9
[ 185619-66-3 ]
5-(3-butyrylamino-phenyl)-isoxazole-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4232 - 4235

10
[ 24424-99-5 ]
[ 185619-66-3 ]

Reference： [1]Tetrahedron,1998,vol. 54,p. 9823 - 9836
[2]Chemical Communications,1996,p. 2647 - 2648
[3]Chemical Communications,2015,vol. 51,p. 5242 - 5245
[4]Chemical Communications,2018,vol. 54,p. 9765 - 9768

11
[ 626-01-7 ]
anilinooxalyl azide [ No CAS ]
[ 185619-66-3 ]

Reference： [1]Tetrahedron,1998,vol. 54,p. 9823 - 9836
[2]Chemical Communications,1996,p. 2647 - 2648

12
[ 143390-49-2 ]
[ 185619-66-3 ]

Reference： [1]Tetrahedron,1998,vol. 54,p. 9823 - 9836
[2]Chemical Communications,1996,p. 2647 - 2648

13
[ 185619-66-3 ]
[ 126146-36-9 ]

Reference： [1]Chemical Communications,1996,p. 2647 - 2648

14
[ 95080-93-6 ]
[ 185619-66-3 ]
[ 745078-83-5 ]

Yield	Reaction Conditions	Operation in experiment
50%	With triethylamine; In tetrahydrofuran;	Example 4B 5-(3-tert-butoxycarbonylamino-phenyl)-isoxazole-3-carboxylic Acid Ethyl Ester <strong>[185619-66-3](3-ethynyl-phenyl)-carbamic acid tert-butyl ester</strong> (2.48 g, 0.0114 mole) and ethyl chlorooximidoacetate (3.82 g, 0.0252 mole) were mixed in THF (12 mL) and triethylamine (3.98 mL, 0.0286 mole) was added slowly. The mixture was stirred for 16 hours and then diluted with ethyl acetate (100 mL) and aqueous 1N HCl (50 mL). The two layers were separated and the aqueous layer extracted with ethyl acetate (2*50 mL). The combined organics were dried over anhydrous Na2SO4, filtered, concentrated in vacuo and purified by flash chromatography (10-15% ethyl acetate/Hexane) to provide the titled compound (2.64 g, 50% yield).
50%	With triethylamine; In tetrahydrofuran; for 16h;	<strong>[185619-66-3](3-ethynyl-phenyl)-carbamic acid tert-butyl ester</strong> (2.48 g, 0.0114 mole) and ethyl chlorooximidoacetate (3.82 g, 0.0252 mole) were mixed in THF (12 mL) and triethylamine (3.98 mL, 0.0286 mole) was added slowly. The mixture was stirred for 16 hours and then diluted with ethyl acetate (100 mL) and aqueous 1N HCl (50 mL). The two layers were separated and the aqueous layer extracted with ethyl acetate (2 50 mL). The combined organics were dried over anhydrous Na 2SO 4, filtered, concentrated in vacuo and purified by flash chromatography (10-15% ethyl acetate/Hexane) to provide the titled compound (2.64 g, 50% yield).

Reference： [1]Patent: US2004/167188,2004,A1
[2]Patent: US2004/214870,2004,A1 .Location in patent: Page 20

15
[ 185619-66-3 ]
[ 74-88-4 ]
[ 857266-55-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium hydride; In tetrahydrofuran; for 5h;	Sodium hydride (60% in mineral oil, 1.0 g) was added portionwise to a solution of tert-butyl 3-ethynylphenylcarbamate (Intermediate 41) (4.50 g) and iodomethane (1.80 mL) in THF (75 mL) and stirred for 5 hours. Water (100 mL) was added and the mixture extracted into ether (3 x 100 mL). The combined organics were washed with water and concentrated in vacuo. Purification by flash chromatography on silica using 0-10% EtOAc in isohexane as eluent gave the title compound as a yellow oil (4.02 g, 84%) ; 'H NMR (CDCl3) 1.45 (s, 9H), 3.06 (s, 1H), 3.25 (s, 3H), 7.22-7. 31 (m, 3H), 7.36 (s, 1H) ; MS m/e (M-CH3) H+ 217

Reference： [1]Patent: WO2005/60970,2005,A1 .Location in patent: Page/Page column 148

16
[ 918487-57-7 ]
[ 185619-66-3 ]
[ 918487-58-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 20 - 40℃; for 2.5h;	EXAMPLE 129; Preparation of N-{3-[2-amino-4-(1-ethyl-5-propionyl-1H-pyrrol-3-yl)-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl]-phenyl}-butyramide; Step a); Preparation of Compound 3; A mixture of 1 (Prepared according to the procedure described in Gang, L. et al., J. Med. Chem. 2003, 46, 4232-4235; 4.08 g, 18.9 mmol), 2 (5.30 g, 17.2 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.36 g, 0.51 mmol), copper(I) iodide (0.064 g, 0.34 mmol) and triethylamine (8.7 g, 86.0 mmol) in dimethylformamide (100 mL) was stirred at room temperature for 1.5 h and then at 40 C. for a further 1 h. After this time, the reaction was cooled to room temperature and diluted with ethyl acetate (300 mL) and water (150 mL). The organic layer was separated and washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography (silica, 80:20 to 50:50 hexanes/ethyl acetate) afforded 2 (4.80 g, 70%) as a dark red oil: 1H NMR (500 MHz, CDCl3) delta 7.56 (br s, 1H), 7.25-7.20 (m, 2H), 7.14 (dt, J=7.2, 1.5 Hz, 1H), 7.06 (d, J=1.7 Hz, 1H), 7.02 (d, J=1.7 Hz, 1H), 6.45 (br s, 1H), 4.32 (q, J=7.2 Hz, 2H), 3.70 (s, 3H), 3.34 (s, 3H), 1.52 (s, 9H), 1.40 (t, J=7.2 Hz, 3H).

Reference： [1]Patent: US2007/4786,2007,A1 .Location in patent: Page/Page column 45-46

17
[ 688-73-3 ]
[ 185619-66-3 ]
[ 185619-68-5 ]

Reference： [1]Chemical Communications,1996,p. 2647 - 2648

18
[ 128140-82-9 ]
[ 185619-66-3 ]
[ 1065168-39-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In acetonitrile; at 60℃; for 1h;	Step b) [3-(4-Difluoromethoxy-phenylethynyl)-phenyl]-carbamic acid tert-butyl ester A mixture of <strong>[185619-66-3](3-ethynyl-phenyl)-carbamic acid tert-butyl ester</strong> (14.7 g, 67.7 mmol), 1-difluoromethoxy-4-iodo-benzene (18.2 g, 67.7 mmol), NEt3 (47 mL, 338 mmol), acetonitrile (225 mL), CuI (1.29 g, 6.77 mmol), and Pd(PPh3)2Cl2 (2.85 g, 4.05 mmol) was heated to 60 C. for 1 h. The reaction was diluted with EtOAc/Hex (1:10) and then passed through a pad of silica gel and concentrated and purified with chromatography using hexanes/ethyl acetate (10:1) as the eluding solvents gave the title compound (24.3 g, 100%), characterized by NMR and mass spectral analyses.

Reference： [1]Patent: US2009/48320,2009,A1 .Location in patent: Page/Page column 39-40

19
[ 5399-03-1 ]
[ 185619-66-3 ]
[ 1192471-75-2 ]

Yield	Reaction Conditions	Operation in experiment
40%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 80℃; for 0.25h;	Step B. tert-Butyl{3-[(2-methoxy-5-nitrophenyl)ethynyl]phenyl}carbamate tert-Butyl (3-ethynylphenyl)carbamate was stirred with 2-iodo-1-methoxy-4-nitrobenzene (2.60 g, 9.31 mmol) and bis(triphenylphosphine)palladium(II) chloride (163 mg, 0.23 mmol) in N,N-dimethylformamide (15 mL), and triethylamine (2.59 mL, 18.6 mmol) was added. The reaction mixture was heated at 80 C. for 15 minutes. Purification by preparative LCMS (pH 10) gave the desired compound (1.38 g, 40%). 1H NMR (300 MHz, DMSO-d6): delta 9.53 (s, 1H), 8.25 (m, 2H), 7.71 (s, 1H), 7.42 (d, 1H), 7.25 (m, 2H), 7.18 (d, 1H), 4.00 (s, 3H), 1.42 (s, 9H). LCMS for C20H21N2O5 (M+H)+: m/z=369.1.

Reference： [1]Patent: US2009/286778,2009,A1 .Location in patent: Page/Page column 79-80

20
[ 185619-66-3 ]
[ 1425647-29-5 ]
[ 1425647-31-9 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 2037 - 2039

21
[ 185619-66-3 ]
[ 25015-63-8 ]
[ 1425647-72-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With (carbonyl)chloro(hydrido)tris(triphenylphosphine)ruthenium(II); In toluene; at 50℃; for 16h;Inert atmosphere;	4,4,5,5-Tetramethyl-1,3,RuH(PPh3)3(CO)CIPhMe,50 ocBocH-n'lf~0x:>< v2-dioxaborolane(16.70 mL,115 mmol)andcarbonylchlorohydridotris(triphenylphosphine)ruthenium(II)(2.63 g,2.76 mmol)were added to anitrogen-purged solution of<strong>[185619-66-3]tert-butyl (3-ethynylphenyl)carbamate</strong>(10 g,46.0 mmol)in toluene(150 mL).The mixture was heated at 50 C for 16 h,whereupon it was concentrated under reduced pressure.Purification by chromatography(silica)eluting with PE/ EtOac(1 00%~ 10: 1)gave the title compound(13.25 g,36.8 mmol,80% yield)as a white solid. LCMS(Method d Table 7)R1=2.19 min; MS m/z =290.1 [M-tBut. 1H NMR(400 MHz,CDCI3)8 1.33(s,12H),1.54(s,9H),6.17(d,J= 18.4 Hz,1H),6.49(bs,1H),7.18(d,J= 7.6 Hz,1H),7.26-7.29(m,1H),7.35-7.40(m,2H),7.47(s,1H).

Reference： [1]Patent: WO2017/210471,2017,A1 .Location in patent: Paragraph 001157; 001158
[2]Chemical Communications,2013,vol. 49,p. 2037 - 2039

22
[ 1143579-89-8 ]
[ 185619-66-3 ]
C₂₃H₂₆N₂O₅ [ No CAS ]