[ CAS No. 5414-19-7 ] {[proInfo.proName]}

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Quality Control of [ 5414-19-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5414-19-7 ]

SDS Specification

Alternatived Products of [ 5414-19-7 ]

Product Details of [ 5414-19-7 ]

CAS No. :	5414-19-7	MDL No. :	MFCD00039196
Formula :	C₄H₈Br₂O	Boiling Point :	-
Linear Structure Formula :	O(CH₂CH₂Br)₂	InChI Key :	FOZVXADQAHVUSV-UHFFFAOYSA-N
M.W :	231.91	Pubchem ID :	21521
Synonyms :		Chemical Name :	1-Bromo-2-(2-bromoethoxy)ethane

Calculated chemistry of [ 5414-19-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	4
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.17
TPSA :	9.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.32
Log Po/w (XLOGP3) :	1.6
Log Po/w (WLOGP) :	1.79
Log Po/w (MLOGP) :	1.89
Log Po/w (SILICOS-IT) :	1.99
Consensus Log Po/w :	1.92

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.02
Solubility :	2.21 mg/ml ; 0.00951 mol/l
Class :	Soluble
Log S (Ali) :	-1.41
Solubility :	9.12 mg/ml ; 0.0393 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.95
Solubility :	0.26 mg/ml ; 0.00112 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.17

Safety of [ 5414-19-7 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	3334
Hazard Statements:	H315-H318-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 5414-19-7 ]

* 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 [ 5414-19-7 ]

[ 5414-19-7 ] Synthesis Path-Downstream 1~14

1
[ 5414-19-7 ]
[ 619-60-3 ]
[ 116104-16-6 ]

Reference： [1]Yaoxue Xuebao/Acta pharmaceutica Sinica,1959,vol. 7,p. 149,152
Chem.Abstr.,1960,p. 5528

2
[ 5414-19-7 ]
[ 66491-03-0 ]
[ 183622-29-9 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4583 - 4591

3
[ 5414-19-7 ]
[ 13130-79-5 ]
[ 1179148-99-2 ]

Yield	Reaction Conditions	Operation in experiment
31%		To a stirred solution of <strong>[13130-79-5]3-amino-1-bromoisoquinoline</strong> (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C. for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. The mixture was stirred further at 25 C. for 5 h and at 75 C. for 72 h before it was cooled to 25 C., quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%). Rt=1.75 min (Cond.-MS-WI); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C13H4BrN2O: 293.03; found: 293.04.
31%		To a stirred solution of 3-amino-l-brotaunoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10175 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 0C for 5 min before 2-bromoethyl ether (90%, 250 DL, 2.00 mmol) was added. The mixture was stirred at 25 0C for 5 h and at 75 0C for 72 h before it was cooled to 25 0C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried with Na2SO4, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%) . Rt = 1.75 min (Cond. -MS-Wl) ; 90% homogenity index; LCMS: Anal. CaIc. for [M+H] + C13H14BrN2O: 293.03; found: 293.04.
31%		To a stirred solution of 3-amino-l-bromoisoquinolirie (444 mg, 2,00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 0C for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. The mixture was stirred at 25 0C for 5 h and at 75 0C for 72 h before it was cooled to 25 0C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried with Na2SC>;4, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%). Rt = 1.75 min (Cond. MS-Wl); 90% homogenity index; LCMS: Anal. CaIc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04.

31%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 25 - 75℃; for 77h;	To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2,4 mmol) in one portion. The mixture was stirred at 25C for 5 min before 2- bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. The mixture was stirred further at 25C for 5 h and at 75 0C for 72 h before it was cooled to 25C} quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO45 filtered and concentrated. Purification of the residue on silica gel elutmg with 0% to 70% ethyl acetate/hexanes afforded Cap- 143, step a as a yellow solid (180 mg, 31%). Rt = 1.75 min (Cond. MS-Wl); 90% homogenily index; LCMS: Anal. CaIc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04.
31%		To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C for 5 min before 2- bromoethyl ether (90%, 250 mu,, 2.00 mmol) was added. The mixture was stirred further at 25 C for 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2S04, filtered andconcentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%). Rt = 1.75 min (Cond.-MS-Wl); 90% homogenity index; LCMS: Anal. Calc. for [M+H C13H14BrN20: 293.03; found: 293.04.
31%		Step a[00254] To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C for 5 min before 2- bromoethyl ether (90%, 250 mu,, 2.00 mmol) was added. The mixture was stirred further at 25 C for 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2S04, filtered andconcentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, Step a as a yellow solid (180 mg, 31%). Rt = 1.75 min(Cond.-MS-Wl); 90% homogenity index; LC-MS: Anal. Calc. for [M+H Ci3H14BrN2 293.03; found: 293.04.
31%	With sodium hydride; In N,N-dimethyl-formamide; at 25 - 75℃; for 77h;	To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C for 5 min before 2-bromoethyl ether (90%, 250 mu, 2.00 mmol) was added. This mixture was stirred further at 25 C for 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2S04, filtered and concentrated. Purification of the residue on silica gel (gradient elution with 0% to 70% ethyl acetate in hexanes) afforded Cap- 143, step a (180 mg, 31%) as a yellow solid. Rt = 1.75 min (Cond.-MS-Wl); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ Ci3H14BrN20: 293.03; found: 293.04.
31%		To a stirred solution of <strong>[13130-79-5]3-amino-1-bromoisoquinoline</strong> (444 mg, 2.00 mmol) in anhydrous dimethylformamide(10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25C for 5 min before 2-bromoethyl ether (90%, 250 mL, 2.00 mmol) was added. This mixture was stirred further at 25 Cfor 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution anddiluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4 filteredand concentrated. Purification of the residue on silica gel (gradient elution with 0% to 70% ethyl acetate in hexanes)afforded Cap-143, step a (180 mg, 31%) as a yellow solid. Rt = 1.75 min (Cond.-MS-W1); 90% homogenity index; LCMS:Anal. Calc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04.
31%		To a stirred solution of <strong>[13130-79-5]3-amino-1-bromoisoquinoline</strong> (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C. for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. This mixture was stirred further at 25 C. for 5 h and at 75 C. for 72 h before it was cooled to 25 C., quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the residue on silica gel (gradient elution with 0% to 70% ethyl acetate in hexanes) afforded Cap-143, step a (180 mg, 31%) as a yellow solid. Rt=1.75 min (Cond.-MS-W1); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04.
		To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C for 5 min before 2-bromoethyl ether (90%, 250 L, 2.00 mmol) was added. The mixture was stirred further at 25 C for 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over a2S04, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap- 143, step a as a yellow solid (180 mg, 31%). Rt = 1.75 min (Cond.-MS-Wl); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ Ci3H14BrN20: 293.03; found: 293.04.

Reference： [1]Patent: US2009/233925,2009,A1 .Location in patent: Page/Page column 55
[2]Patent: WO2010/120621,2010,A1 .Location in patent: Page/Page column 175; 176
[3]Patent: WO2010/138488,2010,A1 .Location in patent: Page/Page column 163
[4]Patent: WO2010/138368,2010,A1 .Location in patent: Page/Page column 120-121
[5]Patent: WO2011/59850,2011,A1 .Location in patent: Page/Page column 112-113
[6]Patent: WO2011/75439,2011,A1 .Location in patent: Page/Page column 107-108
[7]Patent: WO2012/18325,2012,A1 .Location in patent: Page/Page column 110-111
[8]Patent: EP2328865,2017,B1 .Location in patent: Paragraph 0544-0545
[9]Patent: US2010/249190,2010,A1 .Location in patent: Page/Page column 62-63
[10]Patent: WO2011/60000,2011,A1 .Location in patent: Page/Page column 200

4
[ 5414-19-7 ]
[ 214973-83-8 ]
[ 494773-23-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100℃; for 16h;	To a solution of [l-(4-bromo-phenyl)-l-methyl-ethyl]-carbamic acid tert-butyl ester (1 eq) inDMF in a 50 mL tube is added DIPEA (2 eq) and l-bromo-2-(2-bromo-ethoxy)-ethane (1.1 eq). the reaction mixture is heated at 1000C for 16 hrs.. After cooling to room temperature, EtOAc and water are added. The combined organic layers are dried (MgSO/i) and concentrated in vacuo to give the desired product.

Reference： [1]Patent: WO2010/10189,2010,A1 .Location in patent: Page/Page column 71

5
[ 5414-19-7 ]
[ 27489-62-9 ]
[ 1228947-14-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetonitrile; at 60℃;	(0392) Trans-4-Aminocyclohexanol (0.5 g), 1-bromo-2-(2-bromoethoxyl)ethane (1.07 g) and triethylamine (2.42 ml) were dissolved in anhydrous acetonitrile (20 ml). The reaction mixture was heated at 60 C. overnight. The organic solvent was removed under vacuum. The residue was purified with flash column chromatography on silica gel eluting with 7%-10% methanol in dichloromethane to give the title compound.

Reference： [1]Patent: US10213433,2019,B2 .Location in patent: Page/Page column 90

6
[ 5414-19-7 ]
[ 63203-48-5 ]
[ 1430753-58-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N,N-dimethyl-formamide; at 95℃;	Example 160A ethyl 1-morpholinocyclohexanecarboxylate Ethy 1-aminocyclohexancarboxylate hydrogen chloride (5.800 g), triethylamine (13.62 mL) and 1-bromo-2-(2-bromoethoxy)ethane (4.21 mL) were stirred together in N,N-dimethylformamide (50 mL) at 95 C. overnight. The reaction mixture was diluted with ethyl acetate (150 mL), washed with water (100 mL) and brine (100 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with a gradient of 5% to 25% ethyl acetate/hexanes provided the title compound.

Reference： [1]Patent: US2013/96121,2013,A1 .Location in patent: Paragraph 1786

7
[ 5414-19-7 ]
[ 38222-83-2 ]
[ 1621534-73-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; acetonitrile;	Step 1. Preparation of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bS)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(1-morpholinoethyl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate. In a 20 mL scintillation vial were combined methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bS)-1-(1-aminoethyl)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate TFA salt (0.020 g, 0.019 mmol) with 1-bromo-2-(2-bromoethoxy)ethane (0.00883 g, 0.038 mmol) and triethylamine (0.016 mL, 0.114 mmol) in 1,4-dioxane (0.5 mL). The mixture was heated to 85 degrees C. for 30 min which resulted in no reaction. The mixture was transferred to a 5 mL microwave vessel and was diluted with dry acetonitrile (2 mL). To the mixture was added additional 1-bromo-2-(2-bromoethoxy)ethane (another 10 equivalents; 0.0445 g, 0.190 mmol) as well as <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.023 g, 0.114 mmol). The resulting mixture was heated in the microwave to 120 degrees C. for 90 min. The contents of the vessel were concentrated under nitrogen stream, redissolved with a small quantity of a mixture of THF, acetonitrile and methanol, filtered and purified by reverse phase preparative HPLC (Prep HPLC Method 2). The desired product was thus obtained as a white solid and was carried directly into the next step. LCMS: m/z=778.6 (M+H)+, 2.13 min (method 5).

Reference： [1]Patent: US2014/221361,2014,A1 .Location in patent: Page/Page column

8
[ 5414-19-7 ]
[ 36725-28-7 ]
C₁₅H₁₉N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃;	TP5 - To 200 mg (0.984 mmol) of (R)-6-(4-aminophenyl)-5-methyl-4,5- dihydropyridazin-3(2H)-one dissolved in 1 mL of DMF was added 250 (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2CO3 and the mixture was stirred overnight at 60 C. The next day another 250 mu^ of bis (2-bromoethyl) ether and 170 mg of K2CO3 was added. After 3 h, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product (46%). XH NMR (300 MHz, CDC13) delta 8.61 (s, 1H), 7.68 (d, J= 8.8, 2H), 6.92 (d, J= 8.8, 2H), 3.99 - 3.76 (m, 4H), 3.44 - 3.31 (m, 1H), 3.29 - 3.22 (m, 4H), 2.70 (dd, J= 6.7, 16.8, 1H), 2.46 (d, J= 16.7, 1H), 1.24 (d, J= 7.3, 3H). 13C NMR (75 MHz, CDC13) delta 166.64, 154.05, 152.18, 127.10, 125.33, 1 14.73, 66.69, 48.33, 33.93, 27.94, 16.36. MS: 274 (M + 1). Anal. Calcd. for C15H19N3O2: C, 65.91; H, 7.01 ; N, 15.37; Found. 65.81, H, 6.66, N, 15.26.
46%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃;Inert atmosphere;	To 200 mg (0.984 mmol) of A dissolved in 1 mL of Dimethylformamide (DMF) was added 250 mu^ (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2C03 and the mixture was stirred overnight at 60 C. The next day another 250 mu^ oi bis (2-bromoethyl) ether and 170 mg of K2C03 were added. After 3 hours, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product (46%). NMR (300 MHz, CDC13) delta 8.61 (s, 1H), 7.68 (d, J = 8.8, 2H), 6.92 (d, J = 8.8, 2H), 3.99 - 3.76 (m, 4H), 3.44 - 3.31 (m, 1H), 3.29 - 3.22 (m, 4H), 2.70 (dd, J = 6.7, 16.8, 1H), 2.46 (d, J = 16.7, 1H), 1.24 (d, J = 7.3, 3H). 13C NMR (75 MHz, CDC13) delta 166.64, 154.05, 152.18, 127.10, 125.33, 114.73, 66.69, 48.33, 33.93, 27.94, 16.36. TLC: Rf 0.1 (1 :50 MeOH:CH2Cl2). HPLC: Rt 1.05 min, purity > 95%. MS: 274 (M + 1). HRMS: calcd. 274.1556 (M + 1); found 274.1552. Anal. Calcd. for G5H19N3O2: C, 65.91 ; H, 7.01; N, 15.37; Found. 65.81, H, 6.66, N,
46%	With potassium carbonate; In N,N-dimethyl-formamide; at 602℃;Inert atmosphere;	Step 1 ): (0666) To 200 mg (0.984 mmol) of <strong>[36725-28-7](R)-6-(4-aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one</strong> dissolved in 1 mL of DMF was added 250 muIota_ (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2CO3 and the mixture was stirred overnight at 60 C. The next day another 250 muIota_ of bis (2- bromoethyl) ether and 170 mg of K2CO3 was added. After 3 h, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product Compound 3 (46%). 1H NMR (300 MHz, CDCI3) delta 8.61 (s, 1 H), 7.68 (d, J = 8.8, 2H), 6.92 (d, J = 8.8, 2H), 3.99 - 3.76 (m, 4H), 3.44 - 3.31 (m, 1 H), 3.29 - 3.22 (m, 4H), 2.70 (dd, J = 6.7, 16.8, 1 H), 2.46 (d, J = 16.7, 1 H), 1 .24 (d, J = 7.3, 3H). 13C NMR (75 MHz, CDCI3) delta 1 66.64, 154.05, 152.18, 127.1 0, 125.33, 1 14.73, 66.69, 48.33, 33.93, 27.94, 1 6.36. MS: 274 (M + 1 ). Anal. Calcd. for C15H19N3O2: C, 65.91 ; H, 7.01 ; N, 15.37; Found. 65.81 , H, 6.66, N, 15.26.

Reference： [1]Patent: WO2014/164704,2014,A2 .Location in patent: Page/Page column 58; 67
[2]Patent: WO2017/134231,2017,A1 .Location in patent: Page/Page column 91
[3]Patent: WO2018/141835,2018,A1 .Location in patent: Page/Page column 65
[4]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 1537 - 1542

9
[ 5414-19-7 ]
[ 4949-69-3 ]
4-(4-iodo-3-methylphenyl)morpholine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 12664 - 12668
Angew. Chem.,2015,vol. 127,p. 12855 - 12859,5

10
[ 5414-19-7 ]
[ 197376-47-9 ]
ethyl 4-(6-chloropyridin-3-yl)tetrahydro-2H-pyran-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.82 g		To a solution of <strong>[197376-47-9]ethyl (6-chloropyridin-3-yl)acetate</strong> (1.0 g) in N,N-dimethylformamide (20 mL) was added sodium hydride (60% in mineral oil, 0.40 g) under ice-cooling, and the mixture was stirred for 40 min. To the reaction mixture was added 1-bromo-2-(2-bromoethoxy)ethane (2.3 g), and the mixture was stirred at 0 C. for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.82 g). (1596) MS(ESI+): [M+H]+ 270.1

Reference： [1]Patent: US2016/159773,2016,A1 .Location in patent: Paragraph 1594-1596

11
[ 5414-19-7 ]
[ 21230-43-3 ]
ethyl 1-methyl-3-morpholino-1H-pyrazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With caesium carbonate; In N,N-dimethyl acetamide; at 120℃;	A solution of the <strong>[21230-43-3]ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylate</strong> (500 mg, 2.95 mmol), C52CO3 (2.9 g, 8.87 mmol), 1-bromo-2-(2-bromoethoxy) ethane (1.37 g, 5.90 mmol) in DMA(lOmL) as stirred at 120C overnight. Then H20 (20 mL) was added to the mixture and it was extracted with EA(x3). The organic layer was dried and purified by flash to give desired compound as yellow oil (610 mg, 87%). ESI-MS m/z: 240.0 [M+Hjt
87%	With caesium carbonate; In N,N-dimethyl acetamide; at 120℃;	A solution of the <strong>[21230-43-3]ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylate</strong> (500 mg, 2.95 mmol), Cs2CO3 (2.9 g, 8.87 mmol), 1-bromo-2-(2-bromoethoxy) ethane (1.37 g, 5.90 mmol) in DMA (10mL) as stirred at 120 oC overnight. Then H2O (20 mL) was added to the mixture and it was extracted with EA(x3). The organic layer was dried and purified by flash to give desired compound as yellow oil (610 mg, 87%). ESI-MS m/z: 240.0 [M+H]+.

Reference： [1]Patent: WO2017/15449,2017,A1 .Location in patent: Page/Page column 175
[2]Patent: WO2019/67864,2019,A1 .Location in patent: Page/Page column 168-169

12
[ 5414-19-7 ]
[ 99365-40-9 ]
[ 1190861-43-8 ]

Yield	Reaction Conditions	Operation in experiment
31%		n-BuLi (2M in hexane, 22.6 mL, 45.27 mmol) was added drop wise at -40C to a solution of 6-bromo-indolin-2-one (3 g, 14.14 mmol) and diisopropylamine (6.3 mL, 45.27 mmol) in THF (60 mL). The mixture was stirred for 45 min at -40C, 1-bromo-2-(2-bromoethoxy)ethane was added drop wise at this temperature and stirring was continued at RT for 16 h. The reaction mixture was quenched with 4N hydrogen chloride solution (40 mL) and the aqueous phase was separated and extracted with EtOAc (3x 60 mL). The combined organic layers were washed with brine (50 mL), dried over Na2S04 and concentrated. The raw product was triturated with hexane (20 mL) and filtered. The filter was washed with hexane/EtOAc = 4:1 (100 mL) affording the target compound as light brown solid. Yield: 1.2 g (31 %). HPLC (method 1 ): Rt = 2.94 min, m/z [M+H]+ = 282.1 (MW calc. 282.13).

Reference： [1]Patent: WO2017/108204,2017,A1 .Location in patent: Page/Page column 133

13
[ 5414-19-7 ]
[ 56239-26-0 ]
[ 1228947-14-5 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 10071 - 10091

14
[ 5414-19-7 ]
[ 180683-64-1 ]
C₁₅H₂₈N₂O₃ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 99 - 103

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[ CAS No. 5414-19-7 ] {[proInfo.proName]}

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[ 5414-19-7 ] Synthesis Path-Downstream 1~14

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Aliphatic Chain Hydrocarbons

Bromides

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[ 5414-19-7 ]