[ CAS No. 30483-75-1 ] {[proInfo.proName]}

Name: 30483-75-1|4-(4-Bromophenyl)morpholine|98%
Brand: Ambeed
SKU: A257179
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Quality Control of [ 30483-75-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 30483-75-1 ]

SDS Specification

Alternatived Products of [ 30483-75-1 ]

Product Details of [ 30483-75-1 ]

CAS No. :	30483-75-1	MDL No. :	MFCD04112483
Formula :	C₁₀H₁₂BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UJTKZWNRUPTHSB-UHFFFAOYSA-N
M.W :	242.11	Pubchem ID :	11622851
Synonyms :

Calculated chemistry of [ 30483-75-1 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.4
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	59.87
TPSA :	12.47 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.38
Log Po/w (XLOGP3) :	2.05
Log Po/w (WLOGP) :	1.9
Log Po/w (MLOGP) :	2.14
Log Po/w (SILICOS-IT) :	2.64
Consensus Log Po/w :	2.22

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.91
Solubility :	0.299 mg/ml ; 0.00124 mol/l
Class :	Soluble
Log S (Ali) :	-1.94
Solubility :	2.78 mg/ml ; 0.0115 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.44
Solubility :	0.0877 mg/ml ; 0.000362 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.66

Safety of [ 30483-75-1 ]

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 [ 30483-75-1 ]

* 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 [ 30483-75-1 ]
Downstream synthetic route of [ 30483-75-1 ]

[ 30483-75-1 ] Synthesis Path-Upstream 1~20

1
[ 30483-75-1 ]
[ 2524-67-6 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 11, p. 2809 - 2812

2
[ 92-53-5 ]
[ 30483-75-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	at 60℃; for 1 h;	General procedure: In a round-bottomed flask, the substrate (1 mmol) and aqueous HBr(48percent) (1 mL) were mixed in DMSO (1 mL). The mixture was stirredat corresponding temperature for 1–4 h. After cooling to roomtemperature, the reaction was adjusted to pH 7–8 with aqueous NaOHsolution (4 M). Then the mixture was washed twice with EtOAc, andthe combined organic extracts were dried, filtered and concentratedunder reduced pressure to give bromination products.
87%	With C₂₂H₂₄N₄Se₂⁽²⁺⁾*2Br^(1-); dihydrogen peroxide; sodium bromide In 1,4-dioxane; aq. phosphate buffer at 20℃; for 4.5 h;	General procedure: 1,4-Dioxane (5 mL) was added to a mixture of substrate (1.5 mmol) and NaBr (3.09 g, 30 mmol). Catalyst 4a, 2.5 mol percent (25 mg, 0.0375 mmol) was dissolved in 15 mL of a pH 4.2 phosphate solution (NaH₂PO₄ 0.5 M) and added to the reaction mixture. Then, H₂O₂ (8.8 M) was added (the number of equivalents of H₂O₂ is described in Table 3) and the reaction stirred at room temperature for the amount of time reported in Table 3. The products were extracted with ethyl acetate (4×8 mL), the combined organic extracts were washed with 20 mL of NaHSO₃ 0.5 M, 20 mL of brine, dried over MgSO₄, and concentrated under vacuum. When required, purification was performed by column chromatography on flash silica.
85%	With hydrogen bromide; potassium carbonate In dimethyl sulfoxide; ethyl acetate at 60℃; for 0.5 h;	To a mixture of 4-phenylmorpholine (816mg, 5mmol) and DMSO (429mg, 5.5mmol) in ethyl acetate (20mL) was added 84 hydrobromic acid (48percent, 1.85g, 5.5mmol) at 60°C under air. The mixture was stirred at 60°C, then potassium carbonate (1g) was added to the solution and the mixture were stirred for another 0.5h. After cooling down to room temperature and evaporation of the solvent under vacuum, the residue was purified by column chromatography on silica gel with a mixture of hexane and ethyl acetate (10:1) as eluent to give 4-(4-bromophenyl)morpholine as a white solid (1.03g, 85percent yield). ¹H NMR (400MHz, CDCl₃): δ 7.37 (d, 2H, J=8.8Hz), 6.78 (d, 2H, J=8.8Hz), 3.86 (t, 4H, J=4.8Hz), 3.12 (t, 4H, J=4.8Hz). Imidazole (275.6mg, 4.05mmol), 4-(4-bromophenyl)morpholine (700mg, 2.89mmol), K₃PO₄ (1.2g, 5.65mmol) and CuI (110mg, 0.56mmol) in DMF were placed to a closed pressure flask, then stirred at 160°C for 3 days. After cooling to room temperature, distilled water was added to the reaction and the crude was extracted with ethyl acetate. The organic layer was washed with brine and dried over Na₂SO₄. After filtration and evaporation of the solvent under reduced pressure, the residue was purified by column chromatography on silica gel with a mixture of 61 dichloromethane and 62 methanol (30:1) as eluent to give 4-[4-(1H-imidazol-1-yl)phenyl]morpholine (4) as a yellow solid (200mg, 30percent yield). ¹H NMR (400MHz, DMSO-d₆): δ 8.13 (s, 1H, H2), 7.66 (s, 1H, H5), 7.76–7.71 (d, 2H, J=8.8Hz, H8), 7.45 (m, 3H, H4/H9), 3.75 (t, 4H, J=4.8Hz, H12), 3.14 (t, 4H, J=4.8Hz, H11). HRMS (ES⁺): calcd. for C₁₃H₁₆N₃O 230.1293; found 230.1293. A mixture of 4 (150mg, 0.65mmol) and 59 benzyl chloride (121.5mg, 0.96mmol) in acetonitrile was stirred in a closed pressure flask at 80°C for 10h. After cooling down to room temperature, the solution was evaporated to dryness. The residue was purified by column chromatography on silica gel with a mixture of 61 dichloromethane and methanol (10:1) as eluent to give 8 as a highly hydroscopic yellow solid (200mg, 91percent yield). Anal. Calcd. For C₂₀H₂₂ClN₃O: C, 67.50; H, 6.23; N, 11.81. Found: C, 67.57; H, 6.38; N, 11.58. ¹H NMR (400MHz, DMSO-d₆): δ 10.15 (s, 1H, H2), 8.27 (s, 1H, H5), 8.04 (s, 1H, H4), 7.65 (d, 2H, J=8.8Hz, H8), 7.55 (m, 2H, benzyl), 7.47–7.40 (m, 3H, benzyl), 7.15 (d, 2H, J=8.8Hz, H9), 5.52 (s, 2H, H6), 3.76 (t, 4H, J=4.8Hz, H12), 3.22 (t, 4H, J=4.8Hz, H11). ¹³C NMR (100MHz, DMSO-d₆): δ 152.1 (1C, C10), 135.4 (1C, C2), 135.2 (1C, benzyl), 129.4 (2C, benzyl), 129.2 (1C, benzyl), 129.0 (2C, benzyl), 126.4 (1C, C7), 123.4 (1C, C5), 123.1 (2C, H8), 122.1 (1C, C4), 115.6 (2C, H9), 66.4 (2C, C12), 52.6 (1C, C6), 48.2 (2C, C11). HRMS (ES⁺): calcd. for C₂₀H₂₂N₃O 320.1763; found 320.1761.

72%	With bromine In ethanol; water	Reference Example 2c 1-Bromo-4-(4-morpholinyl)benzene Bromine (10.8 g, 67.4 mmol) was added to a solution of (4-morpholinyl)benzene (10.0 g, 61.3 mmol) in ethanol (100 mL) at 0OEC, and the mixture was stirred for 1 hour at room temperature. Water (100 mL) was poured into the reaction mixture, which was then extracted twice with ethyl acetate. The organic layers were combined, washed with an aqueous saturated sodium hydrogencarbonate and water, then dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to obtain the title compound (10.7 g, yield 72 percent). m.p.: 118-120OEC. ¹H-NMR (CDCl₃) δ: 2.98-3.22 (4H, m), 3.71-3.92 (4H, m), 6.72-6.83 (2H, m), 7.31-7.42 (2H, m).
72%	With bromine In ethanol at 0 - 20℃; for 1 h;	Bromine (10.8 g, 67.4 mmol) was added to a solution of 4-(4-morpholinyl)benzene (10.0 g, 61.3 mmol) in ethanol (100 mL) at 0° C., and the mixture was stirred for 1 hour at room temperature. Water (100 mL) was poured into the reaction mixture, which was then extracted twice with ethyl acetate. The organic layers were combined, washed with an aqueous saturated sodium hydrogencarbonate and water, then dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to obtain the title compound (10.7 g, yield 72percent). m.p.: 118-120° C. ¹H-NMR (CDCl₃) δ: 2.98-3.22 (4H, m), 3.71-3.92 (4H, m), 6.72-6.83 (2H, m), 7.31-7.42 (2H, m).
62.9%	With bromine In acetic acid at 20℃; for 1.16667 h;	Zu einer Loesung von 20 g (122.5 mmol) [N-PHENYHNORPHOLIN] in 170 mL Essigsaeure wird bei Raumtemperatur eine Loesung von 6.94 [ML] (134.8 mmol) Brom in 25 mL Essigsaeure ueber einen Zeitraum von [40] min. langsam zugetropft. Nach 30 min. Ruehren bei Raumtemperatur wird das Reaktionsgemisch in 750 mL Wasser ein- geruehrt und mit 45percent-iger Natronlauge auf pH 11 eingestellt. Der entstehende Nieder- schlag wird abgesaugt, mit Wasser gewaschen und im Hochvakuum getrocknet. Nach Umkristallisation aus Ethanol erhaelt man 18.6 g (62.9 percent d. [TH.) DER] Titelverbindung. [LH-NMR] (200 MHz, DMSO-d6) : 8 = 7.37 [(M, 2H),] 6.89 (m, 2H), 3. 73 (m, 4H), 3.08 (m, 4H). HPLC (Methode [1)] : [RT =] 3.9 min. MS (ESIpos) : m/z = 242 (M+H) +.
56.13%	With bromine In ethanol at 0 - 20℃; for 2 h;	To a solution of 4-phenyl-morpholine (18g, 110.4 [MMOL)] in ethanol [(400MOL)] cooled in an iced bath, was added dropwise bromine (5. [95ML,] 116 [MMOL).] The mixture was stirred at room temperature for 2 h and then poured into water. The solution was basified with [NAOH] 1 N. The resulting precipitate was filtered and dried. After crystallisation from diisopropyl ether, the title compound was obtained as white crystals (15g, 56.13percent) ; m. p. [126-128°C.]
56.13%	With bromine In ethanol at 0 - 20℃; for 2 h;	To an ice-cooled solution of 4-phenyl-morpholine (18g, 110.4 [MMOL)] in ethanol (400ml), was added dropwise bromine (5.95 ml, 115.9 [MMOL).] After addition the mixture was warmed to room temperature and stirred for 2 hours. The mixture was poured into water and the solution was basified with 1 N sodium hydroxide solution. The resulting precipitate was filtered, washed with water and dried. Recrystallisation from diisopropyl ether gave the title compound as white crystals (15g, 56.13percent) ; m. p. [ 126-128°C.]
13%	With bromine In ethanol at 0 - 20℃; for 2 h;	To a solution of [4-PHENYLMORPHOLINE (18G,] 110.4 [MMOL)] in ethanol (400ml) cooled in an iced bath, was added dropwise bromine (5.95 ml, 115.9 [MMOL)] and the mixture was stirred at room temperature for 2 hours. The mixture was poured into water and the solution was made basic by addition of a solution of sodium hydroxide [(1N).] The resulting precipitate was filtered, washed with water and dried. Crystallisation from diisopropyl ether gave the title compound as white crystals [(15G,] 56.13percent) ; m. p. 126- [128°C.]

Reference： [1] Organic Letters, 2017, vol. 19, # 16, p. 4243 - 4246
[2] Journal of Chemical Research, 2014, vol. 38, # 10, p. 593 - 596
[3] Organic Letters, 2015, vol. 17, # 12, p. 2886 - 2889
[4] Synthesis, 2009, # 21, p. 3672 - 3676
[5] Synthetic Communications, 2010, vol. 40, # 19, p. 2954 - 2962
[6] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 8, p. 2619 - 2622
[7] Tetrahedron, 2012, vol. 68, # 51, p. 10476 - 10481,6
[8] Tetrahedron Letters, 2007, vol. 48, # 45, p. 7969 - 7973
[9] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 320 - 332
[10] Patent: EP1323716, 2003, A1,
[11] Patent: US7008950, 2006, B1, . Location in patent: Page/Page column 37
[12] Patent: WO2003/104227, 2003, A1, . Location in patent: Page 52, 53
[13] Patent: WO2004/16606, 2004, A1, . Location in patent: Page 23
[14] Patent: WO2004/13138, 2004, A2, . Location in patent: Page 23
[15] Patent: WO2004/13135, 2004, A1, . Location in patent: Page 47-48
[16] Tetrahedron Letters, 2006, vol. 47, # 23, p. 3889 - 3892
[17] Patent: US4139704, 1979, A,
[18] Patent: US4178447, 1979, A,

3
[ 110-91-8 ]
[ 106-37-6 ]
[ 30483-75-1 ]

Yield	Reaction Conditions	Operation in experiment
56%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; for 16 h; Sealed tube; Inert atmosphere	To a 50 mL sealed tube were added R-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.20 g, 0.31 mmol), tris(dibenzylideneacetone)dipalladium (0.095 g, 0.10 mmol), sodium tert-butoxide (0.49 g, 5.0 mmol), p-dibromobenzene (1.00 g, 4.15 mmol) and morpholine (0.37 mL, 4.2 mmol), then anhydrous toluene (8 mL) was added under nitrogen protection. The resulting mixture was stirred for 16 h at an oil bath temperature of 80°C. The reaction mixture was cooled to rt and to the mixture was added EtOAc (20 mL). The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by silica-gel column chromatography (PE:EtOAc=15:1, V/V)to give a white solid (0.56 g, 56percent). MS(ESI, pos.ion)m/z:242.00(M+1)
47%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium <i>tert</i>-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 16 h; Inert atmosphere; Reflux	A solution of tris(dibenzylideneacetone)dipalladium(0) (0.093 g, 0.1 mmol) and (±)-BINAP (0.13 g, 0.21 mmol) in toluene (7 mL) was degassed with argon for 10 min and then heated at 110 °C for 15 min. The reaction mixture was allowed to cool to room temperature before potassiumtert-butoxide (0.53 g, 4.73 mmol), 1,4-dibromobenzene (80) (0.6 g, 2.54 mmol) and morpholine (332 µL, 3.82 mmol) were added. The resulting mixture was heated at reflux for 16 h, cooled to room temperature and filtered through a pad of Celite®, the pad was further washed with toluene (30 mL) and the combined filtrates evaporated under reduced pressure to give the crude product. Purification by flash chromatography on silica eluting with hexane-ethyl acetate (6:1) gave the desired amine81(0.19 g, 47percent) as a colourless solid; mp 110–111 °C;νmax/cm^-12965, 2857, 2831, 1589, 1495, 1259, 1236, 1120, 923, 818; δ_H(300 MHz, CDCl₃) 7.35 (2 H, d,J9.0 Hz), 6.78 (2 H, d,J9.0 Hz), 3.84 (4 H, t,J6.0 Hz), 3.11 (4 H, t,J6.0 Hz);δ_C(75 MHz, CDCl₃) 150.3, 132.0, 117.4, 112.3, 66.8, 49.3;m/z(APCI) 242/244 ([M + H]⁺, 68/100).
26.96%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; johnphos In 1,4-dioxane at 100℃; for 12 h; Sealed tube; Inert atmosphere	To a stirred solution of morpholine (2.0 g, 23.0 mmol), 1, 4-dibromo benzene (19.4 g,82.2 mmol) and 1,4-dioxane (10.0 mL) in sealed tube, 0s2003 (22.4 g, 68.7 mmol)was added and degasified with argon. To the above solution Pd2(dba)3 (0.2 g, 0.22mmol) and 2-(di-tert-butylphosphino)biphenyl (0.6 g, 2.0 mmol) was added andheated at 100 00 for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate, the organic layer was washed with water, brine solution and dried. Finally, concentrated under vacuo and purified by the column chromatography to yield the desired product (1 .5 g, 26.96percent) as a yellow solid. LCMS: (M+2) =244.0; 1HNMR: (ODd3, 300MHz) 6 7.34-7.37 (d, 2H), 6.76-6.79 (d, 2H), 3.84-3.87 (t, 4H),3.10-3.13 (t, 4H).

Reference： [1] Tetrahedron, 2008, vol. 64, # 13, p. 2938 - 2950
[2] Patent: EP3342765, 2018, A1, . Location in patent: Paragraph 0306
[3] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 277 - 301
[4] Patent: WO2014/202580, 2014, A1, . Location in patent: Page/Page column 132; 133
[5] Patent: WO2004/22526, 2004, A1, . Location in patent: Page 66-67

4
[ 110-91-8 ]
[ 589-87-7 ]
[ 30483-75-1 ]

Yield	Reaction Conditions	Operation in experiment
5%	With sodium t-butanolate In tetrahydrofuran at 20℃;	A solution of 1-bromo-4-iodobenzene (5.0 g, 18 mmol), morpholine (1.85 mL, 21 mmol), sodium tert-butoxide (2.4 g, 25 mmol), 18-crown-6 (6.6 g, 25 mmol) in THF (150 mL)was purged with Ar for 20 min, then BINAP (0.11 g, 0.18 mmol) and Pd₂(dba)₃(0.16 g, 0.18 mmol) was added. The mixture turned dark after stirring at room temperature overnight. The solvent was concentrated under reduced pressure and the residue was dissolved in diethyl ether and washed with water. The organic phase was mixed with silica gel, and the solvent was evaporated to dryness. The residue was purified by silica gel column chromatography (EtOAc in hexanes 5percent) to of white precipitate (250 mg, 5percent yield). ¹H NMR (CDCl₃): 7.3 (d, 2H), 6.85 (d, 4H), 3.1 (d, 4H).

Reference： [1] Synthesis, 2009, # 15, p. 2517 - 2522
[2] Journal of Organic Chemistry, 2011, vol. 76, # 3, p. 800 - 810
[3] European Journal of Organic Chemistry, 2010, # 19, p. 3621 - 3630
[4] Patent: US2004/14755, 2004, A1, . Location in patent: Page/Page column 77

5
[ 110-91-8 ]
[ 321970-34-7 ]
[ 30483-75-1 ]

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 25, p. 9563 - 9573

6
[ 92-53-5 ]
[ 30483-75-1 ]
[ 87698-82-6 ]

Reference： [1] Journal of Organic Chemistry, 2008, vol. 73, # 17, p. 6849 - 6852

7
[ 5765-65-1 ]
[ 7519-94-0 ]
[ 30483-75-1 ]

Reference： [1] Organic Letters, 2012, vol. 14, # 16, p. 4230 - 4233

8
[ 110-91-8 ]
[ 66107-30-0 ]
[ 30483-75-1 ]

Reference： [1] Organic Letters, 2004, vol. 6, # 6, p. 985 - 987

9
[ 5765-65-1 ]
[ 183677-71-6 ]
[ 30483-75-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 16, p. 3953 - 3956
[2] Angewandte Chemie - International Edition, 2012, vol. 51, # 15, p. 3642 - 3645

10
[ 5765-65-1 ]
[ 947515-73-3 ]
[ 30483-75-1 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 1, p. 172 - 175

11
[ 110-91-8 ]
[ 106-37-6 ]
[ 30483-75-1 ]
[ 4096-22-4 ]

Reference： [1] Synlett, 2005, # 8, p. 1275 - 1278

12
[ 110-91-8 ]
[ 589-87-7 ]
[ 30483-75-1 ]
[ 4096-22-4 ]

Reference： [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 16, p. 2832 - 2846

13
[ 586-77-6 ]
[ 7460-82-4 ]
[ 30483-75-1 ]

Reference： [1] Synthesis, 2002, # 1, p. 34 - 38

14
[ 110-91-8 ]
[ 106-37-6 ]
[ 92-53-5 ]
[ 30483-75-1 ]

Reference： [1] Tetrahedron Letters, 1999, vol. 40, # 35, p. 6393 - 6397

15
[ 5414-19-7 ]
[ 106-40-1 ]
[ 30483-75-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4242 - 4247

16
[ 5467-74-3 ]
[ 30483-75-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 15, p. 3642 - 3645

17
[ 92-53-5 ]
[ 30483-75-1 ]
[ 87698-82-6 ]

Reference： [1] Journal of Organic Chemistry, 2008, vol. 73, # 17, p. 6849 - 6852

18
[ 30483-75-1 ]
[ 186498-02-2 ]

Reference： [1] Patent: US2004/14755, 2004, A1, . Location in patent: Page/Page column 77

19
[ 30483-75-1 ]
[ 25015-63-8 ]
[ 568577-88-8 ]

Yield	Reaction Conditions	Operation in experiment
83.94%	With triethylamine In 1,4-dioxane for 4 h; Heating / reflux	To a solution of intermediate 24 [(20G,] 82.64 mmol) in dioxane (200ml) was added 4,4, 5, [5-TETRAMETHYL- [1,] 3, [2]-DIOXABORO) ANE (13. 2 M), 99.] 17 [MMOL),] dichloro bis [(TRIPHENYLPHOSPHINE) PALLADIUM (II)] (3g, 4.13 [MMOL)] and triethylamine (34.5 [ML,] 247.93 mmol) and the mixture was heated under reflux during 4 hours and then poured into water. After extraction with [CH2CI2,] the organic phase was dried over [NA2SO4] and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (CH2CI2) to give the title compound as an orange oil which crystallised (19.98 g, 83.94percent) ; [[APCI] MS] m/z 289.07 (MH+).
83.74%	With triethylamine In 1,4-dioxane for 24 h; Heating / reflux	To a solution of intermediate 12 (15g, [62MMOL)] in dioxane (400ml) were added 4,4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane (9. [9MOI,] [68MOL),] [DICHLOROBIS (TRIPHENYLPHOSPHINE) PALLADIUM (LL)] (2. [17G,] 3. 1mmol) and triethylamine (25. 8ml, 186 [MMOL)] and the mixture was heated under reflux for 24 h and then poured into water. After extraction with [CH2CI2,] the organic phase was dried over [NA2SO4] and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with CH2CI2, and after trituration with pentane, the title compound was obtained as a brown solid [(15G,] 83.74percent) ; m. p. [114-116°C.]
83.94%	With triethylamine In 1,4-dioxane for 4 h; Heating / reflux	To a solution of intermediate 8 (20g, 82.64 [MMOL)] in dioxane (200 [ML)] was added 4,4, 5, [5-TETRAMETHYL- [1,] 3, [2]-DIOXABOROLANE] (13.2 ml, 99.17 [MMOL),] dichloro bis [(TRIPHENYLPHOSPHINE) PALLADIUM (11)] (3g, 4.13 [MMOL)] and triethylamine (34. 5 ml, 247.93 [MMOL)] and the mixture was heated under reflux for 4 hours. The reaction mixture was cooled, poured into water and extracted with CH2CI2. The combined organic phases were dried over [NA2SO4] and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with [CH2CI2TO] give the title cornpound was obtained as an orange oil which crystallised (19.98 g, 83.94percent) ; [[APCI] MS] m/z 289.07 [(MH+).]

Reference： [1] Patent: WO2004/13135, 2004, A1, . Location in patent: Page 48-49
[2] Patent: WO2004/16606, 2004, A1, . Location in patent: Page 25
[3] Patent: WO2004/13138, 2004, A2, . Location in patent: Page 23; 24

20
[ 30483-75-1 ]
[ 73183-34-3 ]
[ 568577-88-8 ]

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3820 - 3832
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7543 - 7546

[ 30483-75-1 ] Synthesis Path-Downstream 1~88

1
4-(4-morpholino-phenylazo)-morpholine [ No CAS ]
[ 30483-75-1 ]

Reference： [1]Journal of the American Chemical Society,1943,vol. 65,p. 479

2
[ 30483-75-1 ]
[ 88799-18-2 ]

Reference： [1]Chemische Berichte,1983,vol. 116,p. 3539 - 3551

3
[ 30483-75-1 ]
[ 890316-40-2 ]
tert-butyl 2-(4-morpholinoanilino)-4-phenylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To toluene 3.0mL solution of tert-butyl 2-amino-4-phenylbenzoate 94mg were added <strong>[30483-75-1]<strong>[30483-75-1]4-(4-bromophenyl)morpholin</strong>e</strong> 0.21g, cesium carbonate 0.23g, tris(dibenzylideneacetone)dipalladium(0) 3.2mg and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl 8.3mg at room temperature, and it was stirred at 110C for 6 hours. After the reaction mixture was cooled to room temperature, palladium acetate 1.6mg, tris(dibenzylideneacetone)dipalladium(0) 3.2mg and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl 8.3mg were added, and it was stirred at 110C for 12 hours. After the reaction mixture was cooled to room temperature, <strong>[30483-75-1]<strong>[30483-75-1]4-(4-bromophenyl)morpholin</strong>e</strong> 0.21g, cesium carbonate 0.23g, palladium acetate 1.6mg, tris(dibenzylideneacetone)dipalladium(0) 3.2mg and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl 8.3mg were added, and it was stirred at 110C for 4 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=4:1] to give tert-butyl 2-(4-morpholinoanilino)-4-phenylbenzoate. Trifluoroacetic acid 10mL was added to the obtained tert-butyl 2-(4-morpholinoanilino)-4-phenylbenzoate, and it was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 50-80% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-(4-morpholinoanilino)-4-phenylbenzoic acid 31mg of a yellow solid. 1H-NMR(DMSO-d6) delta value: 3.10(4H,t,J=4.8Hz),3.74(4H,t,J=4.8Hz),6.93-6.99(1H,m),6.99(2H,d,J=8.8Hz),7.15-7.19(1H,m),7.21(2H,d,J=8.8Hz),7.35-7.47(3H,m),7.50-7.55(2H,m),7.94(1H,d,J=8.3Hz),9.50(1H,s),12.96(1H,s).

Reference： [1]Patent: EP1860098,2007,A1 .Location in patent: Page/Page column 115-116

4
[ 30483-75-1 ]
[ 51-90-1 ]
[ 693242-87-4 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2007,vol. 50,p. 412 - 413

5
[ 30483-75-1 ]
[ 2298-07-9 ]
C₂₀H₂₀N₂O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4242 - 4247

6
[ 5414-19-7 ]
[ 106-40-1 ]
[ 30483-75-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4242 - 4247

7
[ 30483-75-1 ]
1-[5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl]-3-[4-(4-(morpholin-4-yl)phenyl)naphthalen-1-yl]urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4242 - 4247

8
[ 106-41-2 ]
concentrated aqueous KOH-solution [ No CAS ]
[ 30483-75-1 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 9563 - 9573

9
[ 30483-75-1 ]
[ 30483-78-4 ]

Reference： [1]Journal of the Chemical Society C: Organic,1971,p. 132 - 137

10
[ 30483-75-1 ]
[ 31618-92-5 ]

Reference： [1]Journal of the Chemical Society C: Organic,1971,p. 132 - 137

11
[ 30483-75-1 ]
[ 30483-77-3 ]

Reference： [1]Journal of the Chemical Society C: Organic,1971,p. 132 - 137

12
[ 30483-75-1 ]
[ 31618-93-6 ]

Reference： [1]Journal of the Chemical Society C: Organic,1971,p. 132 - 137

13
[ 30483-75-1 ]
[ 634905-12-7 ]

Yield	Reaction Conditions	Operation in experiment
35.7%	With potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride; In dichloromethane; for 5h;Heating / reflux;	Zu einer Loesung von 500 mg (2.07 mmol) 4- (4-Bromphenyl) morpholin (Beispiel 15A) in 10 [ML] Dichlormethan werden 1.41 g (6. [20 MMOL)] Benzyltriethylammonium- chlorid und 0.98 g (6.20 mmol) Kaliumpermanganat gegeben. Nach 5 h unter Rueck- fluss wird der Kolbeninhalt im Vakuum eingeengt und der Rueckstand mittels praeparativer HPLC aufgereinigt. Das eingeengte Produkt wird im Hochvakuum getrocknet. Man erhaelt 217 mg (35.7 [%] d. Th. ) der Titelverbindung. LC-MS (Methode 4) : Rt = 2.9 min, m/z = 255 [(M+).]

Reference： [1]Patent: WO2003/104227,2003,A1 .Location in patent: Page 53

14
[ 110-91-8 ]
[ 106-37-6 ]
[ 30483-75-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium hydroxide; at 60℃; for 0.5h;Green chemistry;Catalytic behavior;	General procedure: In a round-bottomed flask equipped with mechanical stirrer,aryl halide (1 mmol), amine (1.2 mmol), catalyst (5 mg) and KOH(2 mmol) were stirred in ethanol (5 ml) under air atmosphere at 60C for 0.5 h. The progress of the reaction was monitored by TLC and GC. After completion of the reaction, CH2Cl2 (15 ml) was added and the catalyst was separated using an external magnet. The organic layer was washed with water (3 x 10 ml) and dried over anhydrous MgSO4. The product was isolated by column chromatography (nhexaneeethylacetate, 5:1) to afford the corresponding products.The products were characterized by their physical properties,melting points, and FT-IR, 1H NMR and 13C NMR [69-71].
56%	With tris-(dibenzylideneacetone)dipalladium(0); (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 80℃; for 16h;Sealed tube; Inert atmosphere;	To a 50 mL sealed tube were added R-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.20 g, 0.31 mmol), tris(dibenzylideneacetone)dipalladium (0.095 g, 0.10 mmol), sodium tert-butoxide (0.49 g, 5.0 mmol), p-dibromobenzene (1.00 g, 4.15 mmol) and morpholine (0.37 mL, 4.2 mmol), then anhydrous toluene (8 mL) was added under nitrogen protection. The resulting mixture was stirred for 16 h at an oil bath temperature of 80C. The reaction mixture was cooled to rt and to the mixture was added EtOAc (20 mL). The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by silica-gel column chromatography (PE:EtOAc=15:1, V/V)to give a white solid (0.56 g, 56%). MS(ESI, pos.ion)m/z:242.00(M+1)
47%	With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; for 16h;Inert atmosphere; Reflux;	A solution of tris(dibenzylideneacetone)dipalladium(0) (0.093 g, 0.1 mmol) and (±)-BINAP (0.13 g, 0.21 mmol) in toluene (7 mL) was degassed with argon for 10 min and then heated at 110 C for 15 min. The reaction mixture was allowed to cool to room temperature before potassiumtert-butoxide (0.53 g, 4.73 mmol), 1,4-dibromobenzene (80) (0.6 g, 2.54 mmol) and morpholine (332 muL, 3.82 mmol) were added. The resulting mixture was heated at reflux for 16 h, cooled to room temperature and filtered through a pad of Celite, the pad was further washed with toluene (30 mL) and the combined filtrates evaporated under reduced pressure to give the crude product. Purification by flash chromatography on silica eluting with hexane-ethyl acetate (6:1) gave the desired amine81(0.19 g, 47%) as a colourless solid; mp 110-111 C;numax/cm-12965, 2857, 2831, 1589, 1495, 1259, 1236, 1120, 923, 818; deltaH(300 MHz, CDCl3) 7.35 (2 H, d,J9.0 Hz), 6.78 (2 H, d,J9.0 Hz), 3.84 (4 H, t,J6.0 Hz), 3.11 (4 H, t,J6.0 Hz);deltaC(75 MHz, CDCl3) 150.3, 132.0, 117.4, 112.3, 66.8, 49.3;m/z(APCI) 242/244 ([M + H]+, 68/100).

26.96%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; johnphos; In 1,4-dioxane; at 100℃; for 12h;Sealed tube; Inert atmosphere;	To a stirred solution of morpholine (2.0 g, 23.0 mmol), 1, 4-dibromo benzene (19.4 g,82.2 mmol) and 1,4-dioxane (10.0 mL) in sealed tube, 0s2003 (22.4 g, 68.7 mmol)was added and degasified with argon. To the above solution Pd2(dba)3 (0.2 g, 0.22mmol) and 2-(di-tert-butylphosphino)biphenyl (0.6 g, 2.0 mmol) was added andheated at 100 00 for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate, the organic layer was washed with water, brine solution and dried. Finally, concentrated under vacuo and purified by the column chromatography to yield the desired product (1 .5 g, 26.96%) as a yellow solid. LCMS: (M+2) =244.0; 1HNMR: (ODd3, 300MHz) 6 7.34-7.37 (d, 2H), 6.76-6.79 (d, 2H), 3.84-3.87 (t, 4H),3.10-3.13 (t, 4H).
	With potassium tert-butylate;tris-(dibenzylideneacetone)dipalladium(0); johnphos; In 1,4-dioxane; for 20h;Heating / reflux;	EXAMPLE 35; Synthesis of (2S)-N-(Cyanomethyl)-4-methyl-2-[(R)-(4'-morpholin-4-yl-1,1 '-biphenyl-4-yl)(phenyl)methyl]oxy}pentanamide; Step 1; 4-(4-Bromophenyl)morpholine;To a solution of of morpholine (0.85 mmol, 739 mg) in dioxane (12 mL) was added 1,4-dibromobenzene (21.2 mmol, 5 g), 2-(di-t-butylphosphine)biphenyl (1.02 mmol, 304mg), potassium t-butoxide (25.5 mmol, 2.47 g) and Pd2(dba)3 (0.254 mmol, 233 mg). The mixture was degassed under a stream of nitrogen and then heated to reflux for 20 h. The mixture was diluted with EtOAc and washed with water and brine. The organic extract was concentrated under reduced pressure and the residue was chromatographed to give the desired product

Reference： [1]Journal of Organometallic Chemistry,2019,vol. 899
[2]Tetrahedron,2008,vol. 64,p. 2938 - 2950
[3]Patent: EP3342765,2018,A1 .Location in patent: Paragraph 0306
[4]European Journal of Medicinal Chemistry,2015,vol. 95,p. 277 - 301
[5]Patent: WO2014/202580,2014,A1 .Location in patent: Page/Page column 132; 133
[6]Patent: WO2004/22526,2004,A1 .Location in patent: Page 66-67

15
(2S)-N-(cyanomethyl)-4-methyl-2-{phenyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methoxy}pentanamide [ No CAS ]
[ 30483-75-1 ]
(2S)-N-(cyanomethyl)-4-methyl-2-[(R)-(4'-morpholin-4-yl-1,1 '-biphenyl-4-yl)(phenyl)methvl]oxy}pentanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 85℃; for 18h;	Step 2; (2S)-N-(Cyanomethyl)-4-methyl-2-[(R)-(4'-morpholin-4-yl-1,1 '-biphenyl-4-yl)(phenyl)methvl]oxy}pentanamide;To a solution of <strong>[30483-75-1]N-(4-bromophenyl)morpholine</strong> (0.66 mmol, 159 mg) in DMF (7 mL) was added under a stream of nitrogen (2S)-N-(cyanomethyl)-4-methyl-2-{phenyl[4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methoxy}pentanamide from Example 16 (0.66mmol, 250 mg). PdCl2(dppf) (0.033 mmol, 24 mg) and 2N Na2CO3 (2.63 mmol) was added. The mixture was degassed with a rapid stream of nitrogen bubbling through the mixture and the mixture was heated to 85 C for 18 h. EtOAc was added, the mixture was washed with water and brine. The organic extract was dried and chromatographed (20-40% EtOAc/hexane) to give the title compound. MS (-ESI) 496 [M-1]-

Reference： [1]Patent: WO2004/22526,2004,A1 .Location in patent: Page 67

16
[ 110-91-8 ]
[ 589-87-7 ]
[ 30483-75-1 ]

Yield	Reaction Conditions	Operation in experiment
5%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; at 20℃;	A solution of 1-bromo-4-iodobenzene (5.0 g, 18 mmol), morpholine (1.85 mL, 21 mmol), sodium tert-butoxide (2.4 g, 25 mmol), 18-crown-6 (6.6 g, 25 mmol) in THF (150 mL)was purged with Ar for 20 min, then BINAP (0.11 g, 0.18 mmol) and Pd2(dba)3(0.16 g, 0.18 mmol) was added. The mixture turned dark after stirring at room temperature overnight. The solvent was concentrated under reduced pressure and the residue was dissolved in diethyl ether and washed with water. The organic phase was mixed with silica gel, and the solvent was evaporated to dryness. The residue was purified by silica gel column chromatography (EtOAc in hexanes 5%) to of white precipitate (250 mg, 5% yield). 1H NMR (CDCl3): 7.3 (d, 2H), 6.85 (d, 4H), 3.1 (d, 4H).

Reference： [1]Synthesis,2009,p. 2517 - 2522
[2]Journal of Organic Chemistry,2011,vol. 76,p. 800 - 810
[3]European Journal of Organic Chemistry,2010,p. 3621 - 3630
[4]Patent: US2004/14755,2004,A1 .Location in patent: Page/Page column 77

17
[ 30483-75-1 ]
[ 186498-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; ethyl acetate; pentane; at -78 - 20℃;	To a solution of the compound prepared in step 1 (0.3 g) in THF (15 mL) was added n-BuLi (0.74 mL, 2 M in pentane) at -78 C. After 1 h triisopropyl borate (0.86 mL) was added at -78 C. The solution was warmed up slowly from -78 C. to room temperature and was stirred overnight. The solution was added to aqueous NH4Cl, a white precipitate formed, and EtOAc was added. The organic solution was separated, concentrated and co-evaporated with toluene. The residue was washed twice with THF and filtered. The filtrate was concentrated and dried under high vacuum to give 0.25 g of light yellow precipitate. LC/MS m/z 208 (M+H)+.

Reference： [1]Patent: US2004/14755,2004,A1 .Location in patent: Page/Page column 77

18
N-isobutyryl-2-methyl aziridine [ No CAS ]
[ 109-72-8 ]
[ 30483-75-1 ]
[ 216989-48-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	In tetrahydrofuran; water;	Reference Example 4c 2-Methyl-1-[4-(4-morpholinyl)phenyl]propan-1-one n-Butyllithium (1.6 M, 25.8 mL, 41.3 mmol) was added to a solution of <strong>[30483-75-1]1-bromo-4-(4-morpholinyl)benzene</strong> (10.0 g, 41.3 mmol) in tetrahydrofuran (100 mL) at -78ØC, and the mixture was stirred for 20 minutes at the same temperature. To the reaction mixture was added N-isobutyrylpropyleneimine (5.77 g, 45.4 mmol), and the mixture was stirred for 30 minutes at room temperature. Water (40 mL) was poured into the reaction mixture, which was then extracted twice with ethyl acetate. The organic layers were combined, washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was crystallized from hexane to obtain the title compound (6.50 g, yield 67 %). m.p.: 75-77ØC. 1H-NMR (CDCl3) delta: 1.19 (6H, d, J = 7.0 Hz), 3.22-3.33 (4H, m), 3.50 (1H, septet, J = 7.0 Hz), 3.81-3.92 (4H, m), 6.81-6.92 (2H, m), 7.85-8.95 (2H, m).

Reference： [1]Patent: EP1323716,2003,A1

19
[ 30483-75-1 ]
[ 87199-17-5 ]
[ 893739-03-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 7715 - 7727

20
[ 30483-75-1 ]
[ 1093845-65-8 ]
C₃₁H₃₁N₂O₂S⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 9745 - 9756

21
[ 30483-75-1 ]
[ 1205-17-0 ]
[ 1070716-76-5 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 4561 - 4564

22
[ 591-12-8 ]
[ 30483-75-1 ]
[ 1160526-70-4 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 2663 - 2666

23
[ 30483-75-1 ]
[ 7031-01-8 ]
3,6-bis(N,N-dimethylamino)-9-(4-morpholinophenyl)thioxanthylium hexafluorophosphate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3328 - 3341

24
[ 30483-75-1 ]
[ 1142944-76-0 ]
N-(4-morpholinophenyl)-5-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15.8%		After the mixture of 5-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine (100 mg, 0.47 mmol), 4-(4-bromo-phenyl)-morpholine (137 mg, 0.57 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (27 mg, 0.047 mmol) and potassium tert-butoxide (105 mg, 0.94 mmol) in dioxane (6 mL) was degassed, tris(dibenzylideneacetone)-dipalladium (0) (21.6 mg, 0.024 mmol) was added under nitrogen, and the reaction mixture was heated at 80 C. with stirring under nitrogen overnight. The reaction mixture was quenched by the addition of water, and the mixture was extracted with ethyl acetate (15 mL×3). The combined organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by preparative TLC (eluting with 25% ethyl acetate in petroleum ether) to give N-(4-morpholinophenyl)-5-phenyl-[1,2,4]triazolo[1,5-c]pyridin-2-amine as free base, which was converted to the corresponding hydrochloride salt with methanolic hydrochloride solution (28 mg, 15.8% yield). 1H NMR (400 MHz, DMSO-d6) delta (ppm) 9.91 (br s, 1H), 8.02 (d, J=8.0 Hz, 2H), 7.75-7.52 (m, 9H), 7.20 (d, J=6.8 Hz, 1H), 3.97 (s, 4H), 3.45 (s, 4H); MS (ESI): m/z 372.2 [M+1]+.

Reference： [1]Patent: US2010/93698,2010,A1 .Location in patent: Page/Page column 93

25
[ 30483-75-1 ]
[ 27329-70-0 ]
[ 1001010-56-5 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; ethanol; water; at 80℃; for 18.1667h;Inert atmosphere;	The reaction flask was flushed with nitrogen and charged with 4-(4-bromo-phenyl)-morpholine (2.134 g, 8.81 mmol), 5-formyl-furan-2-boronic acid (1.832 g, 13.10 mmol) and sodium carbonate (3.016 g, 28.46 mmol). A mixture of 1,2-dimethoxyethane (35 mL), ethanol (10 mL) and water (13 mL) was added and the reaction mixture was stirred for 10 min under a nitrogen atmosphere. Dichlorobis(triphenylphosphine) palladium(II) (0.205 g, 0.29 mmol) was added and the mixture was stirred and heated at 80 C. for 18 h. The mixture was cooled to room temperature and partitioned between ether (250 mL) and water (100 mL). The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on flash Silica (100 mL, 20% ethyl acetate in hexanes) to afford 5-(4-morpholin-4-yl-phenyl)-furan-2-carbaldehyde (1.36 g, 60%). 1H NMR (400 MHz, CDCl3): delta 3.26 (2H, dd, J=5.2, 3.6 Hz), 3.87 (2H, dd, J=5.2, 3.6 Hz), 6.69 (1H, d, J=4.0 Hz), 6.93 (2H, m), 7.26 (1H, s), 7.30 (1H, d, J=4.0), 7.74 (2H, m), 9.58 (1H, s). ESI-MS: 258.0.

Reference： [1]Patent: US2010/210577,2010,A1 .Location in patent: Page/Page column 31

26
[ 30483-75-1 ]
[ 87199-18-6 ]
[ 1233720-64-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3494 - 3505

27
N-isobutyryl-2-methyl aziridine [ No CAS ]
[ 30483-75-1 ]
[ 216989-48-9 ]

Yield	Reaction Conditions	Operation in experiment
67%		n-Butyllithium (1.6 M, 25.8 mL, 41.3 mmol) was added to a solution of <strong>[30483-75-1]1-bromo-4-(4-morpholinyl)benzene</strong> (10.0 g, 41.3 mmol) in tetrahydrofuran (100 mL) at -78 C., and the mixture was stirred for 20 minutes at the same temperature. To the reaction mixture was added N-isobutyrylpropyleneimine (5.77 g, 45.4 mmol), and the mixture was stirred for 30 minutes at room temperature. Water (40 mL) was poured into the reaction mixture, which was then extracted twice with ethyl acetate. The organic layers were combined, washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was crystallized from hexane to obtain the title compound (6.50 g, yield 67%). m.p.: 75-77 C. 1H-NMR (CDCl3) delta: 1.19 (6H, d, J=7.0 Hz), 3.22-3.33 (4H, m), 3.50 (1H, septet, J=7.0 Hz), 3.81-3.92 (4H, m), 6.81-6.92 (2H, m), 7.85-8.95 (2H, m).

Reference： [1]Patent: US7008950,2006,B1 .Location in patent: Page/Page column 37-38

28
[ 30483-75-1 ]
[ 1257704-10-1 ]
[ 1257704-11-2 ]
[ 1257704-09-8 ]

Yield	Reaction Conditions	Operation in experiment
41%; 20%	With caesium carbonate;palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 80℃; for 72h;Inert atmosphere; Sealed tube;	To an oven dried tube was added palladium acetate (10.0 mg, 0.0445 mmol) and 9,9- dimethyl-4,5-bis(diphenylphosphino)xanthene (75.0 mg, 0.130 mmol), 8-(2-methoxy- phenyl)-[l,2,4]triazolo[l,5-a]pyridin-2-ylamine (100.0 mg, 0.4162 mmol), 4-(4-bromo- phenyl)-morpholine (120.0 mg, 0.4956 mmol), cesium carbonate (270 mg, 0.83 mmol) and 1,4-dioxane (5 mL). The tube was evacuated and backflushed with nitrogen three times. The tube was sealed and heated at 800C for 72 hours. The mixture was cooled to room temperature, diluted with dichloromethane (10 mL), filtered through a plug of diatomaceous earth, rinsed with dichloromethane and evaporated. The material was purified via chromatography utilizing an ISCO automated purification apparatus (amine modified silica gel column 5% - >;100% ethyl acetate in hexanes). The title compound, [8- (2-Methoxy-phenyl)-[ 1 ,2,4]triazolo[ 1 ,5-a]pyridin-2-yl]-(4-morpholin-4-yl-phenyl)-amine, was isolated as a pale yellow foam (0.034 g, 20%). 1H NMR (400 MHz, CDCl3, delta, ppm): 8.39 (dd, J=6.7, 1.1 Hz, IH), 7.61 (dd, J=I.5, 1.7 Hz, IH), 7.51 (dd, J=I.3, 0.9 Hz, IH), 7.50-7.45 (m, 2H), 7.43-7.37 (m, IH), 7.12-7.07 (m, IH), 7.05 (d, J=S.2, IH), 6.96-6.87 (m, 3H), 6.67 (s, IH), 3.89-3.85 (m, 4H), 3.81 (s, 3H), 3.12-3.08 (m, 4H). MS = 402 (MH)+. [8-(2-Methoxy-phenyl)-[l ,2,4]triazolo[l ,5-a]pyridin-2-yl]-phenyl-amine (0.054 g, 41%), was a byproduct of the reaction and was isolated as a off-white solid. MP = 141-145 0C. 1H NMR (400 MHz, CDCl3, delta, ppm): 8.42 (dd, J=6.6, 0.9 Hz, IH), 7.62 (dd, J=I.5, 1.7, IH), 7.58-7.52 (m, 3H), 7.44-7.38 (m, IH), 7.36-7.30 (m, 2H), 7.10 (t, J=7.5 Hz, IH), 7.05 (d, J=8.3 Hz, IH), 6.97 (t, J=7.4 Hz, IH), 6.93 (t, J=I lambda Hz, IH), 6.87 (s, IH), 3.82 (s, 3H). MS = 317 (MH)+.

Reference： [1]Patent: WO2010/141796,2010,A2 .Location in patent: Page/Page column 133; 134

29
[ 30483-75-1 ]
[ 121-43-7 ]
C₁₂H₁₈BNO₃ [ No CAS ]

Reference： [1]Synthesis,2010,p. 4033 - 4042

30
[ 30483-75-1 ]
[ 109-73-9 ]
[ 1038225-23-8 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 800 - 810

31
[ 30483-75-1 ]
3-methyl-4-(4-((trifluoromethyl)thio)phenyl)oxy-1-nitrobenzene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7312 - 7314
[2]Angewandte Chemie - International Edition,2011,vol. 50,p. 7312 - 7314

32
[ 30483-75-1 ]
[ 811-68-7 ]
[ 1333415-77-2 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7312 - 7314

33
[ 30483-75-1 ]
cesium trifluoromethanethiolate [ No CAS ]
[ 1333415-77-2 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7312 - 7314

34
[ 30483-75-1 ]
tetramethylammonium trifluoromethanethiolate [ No CAS ]
[ 1333415-77-2 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7312 - 7314

35
[ 30483-75-1 ]
[ 21273-02-9 ]
[ 1351403-44-5 ]
[ 1351403-43-4 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 9943 - 9947

36
[ 30483-75-1 ]
[ 108-93-0 ]
[ 1351403-28-5 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 9943 - 9947

37
[ 30483-75-1 ]
[ 71-36-3 ]
[ 1351403-35-4 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1580 - 1583
[2]Angewandte Chemie - International Edition,2011,vol. 50,p. 9943 - 9947

38
[ 30483-75-1 ]
[ 22385-77-9 ]
[ 1360592-38-6 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 10665 - 10669

39
[ 30483-75-1 ]
[ 131211-27-3 ]
[ 1353642-32-6 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 1056 - 1071

40
[ 30483-75-1 ]
potassium ferrocyanide [ No CAS ]
[ 10282-31-2 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 2978 - 2986

41
[ 5765-65-1 ]
[ 183677-71-6 ]
[ 30483-75-1 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 3953 - 3956
[2]Angewandte Chemie - International Edition,2012,vol. 51,p. 3642 - 3645

42
[ 5467-74-3 ]
[ 30483-75-1 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 3642 - 3645

43
[ 30483-75-1 ]
[ 105-56-6 ]
[ 10282-31-2 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3644 - 3647

44
[ 30483-75-1 ]
[ 1257704-13-4 ]
[ 1257704-12-3 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5243 - 5254

45
[ 5765-65-1 ]
[ 7519-94-0 ]
[ 30483-75-1 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 4230 - 4233

46
[ 30483-75-1 ]
[ 1309388-62-2 ]
[ 1407153-85-8 ]
(-)-(4R)-1-methyl-4-(4-morpholinobenzyl)-3-(4-nitrophenyl)imidazolidin-2-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 9886 - 9890
Angewandte Chemie,2012,vol. 124,p. 10024 - 10028

47
[ 30483-75-1 ]
[ 1415309-81-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7543 - 7546

48
[ 150879-48-4 ]
[ 30483-75-1 ]
[ 1299312-89-2 ]

Yield	Reaction Conditions	Operation in experiment
64%		Scheme 19: To a cooled (-80 C, dry ice/Et20) mixture of 2 (0.577 g, 1.0 equiv) and bromide 3 (0.650 g, 1.0 equiv) in 30 mL dry THF under an argon atmosphere was added n- BuLi (2.5 M in hexanes, 2.2 mL, 2.05 equiv) dropwise. The mixture was stirred at the same temperature for 30 min and quenched with 1M aq. HCl and extracted with EtOAc (3 x 50 mL). The combined EtOAc extracts were dried over MgS04, filtered, concentrated in vacuo, and the residue obtained was dissolved in minimal amount of CH2C12 and loaded directly onto the ISCO (silica gel) column (0-30% EtOAc/Hexanes) which gave 4 (0.542 g, yield: 64%) as a yellow solid.

Reference： [1]Patent: WO2011/53697,2011,A1 .Location in patent: Page/Page column 83-84

49
[ 5765-65-1 ]
[ 947515-73-3 ]
[ 30483-75-1 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 172 - 175

50
[ 30483-75-1 ]
[ 1432450-83-3 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 3820 - 3832

51
[ 30483-75-1 ]
(3-methylbut-2-en-1-yl)zinc(II) bromide lithium chloride [ No CAS ]
4-(4-(3-methylbut-2-en-1-yl)phenyl)morpholine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 14098 - 14102
Angew. Chem.,2013,vol. 125,p. 14348 - 14352,5

52
[ 30483-75-1 ]
[ 1571072-87-1 ]

Reference： [1]Patent: US2014/66445,2014,A1

53
[ 30483-75-1 ]
KX₂-361 [ No CAS ]

Reference： [1]Patent: US2014/66445,2014,A1
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 4704 - 4719

54
[ 30483-75-1 ]
[ 1571072-91-7 ]

Reference： [1]Patent: US2014/66445,2014,A1
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 4704 - 4719

55
[ 30483-75-1 ]
[ 1571072-93-9 ]

Reference： [1]Patent: US2014/66445,2014,A1
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 4704 - 4719

56
[ 30483-75-1 ]
[ 351019-18-6 ]
[ 1571072-90-6 ]

Reference： [1]Patent: US2014/66445,2014,A1 .Location in patent: Paragraph 0393
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 4704 - 4719

57
[ 30483-75-1 ]
(E)-N-(2-methylpropylidene)-9H-fluoren-9-amine [ No CAS ]
[ 1580458-71-4 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 4500 - 4503

58
[ 30483-75-1 ]
C₃₆H₄₆N₄O₇ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 248 - 258

59
[ 30483-75-1 ]
[ 1608463-97-3 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 248 - 258

60
[ 30483-75-1 ]
4-(4-azidophenyl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; copper(ll) sulfate pentahydrate; sodium carbonate; sodium L-ascorbate; L-proline; In water; N,N-dimethyl-formamide; at 85℃;	General procedure: A: For aryl azides: Sodium ascorbate (59.4 mg, 0.3 mmol) and CuSO4*5H2O (23 mg, 0.12 mmol) were added to a mixture of aryl bromide (0.6 mmol), sodium azide (59.1 mg, 0.9 mmol), L-proline (13.8 mg, 0.12 mmol) and Na2CO3 (12.7 mg, 0.12 mmol) in 2 mL of DMF/H2O (2:1). The mixture was stirred overnight at 85 C. Then water (8 mL) and concentrated NH4OH (2 mL) were added and the crude mixture was extracted with ether (10 mL x 3), then the combined organic layers were washed with saturated NH4Cl solution and brine, dried over Na2SO4 (anhydrous), filtered and concentrated to give a crude azido compound, which was used as such in the subsequent step.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 248 - 258

61
[ 30483-75-1 ]
C₁₈H₂₁NO [ No CAS ]
C₂₈H₃₂N₂O₂ [ No CAS ]
C₂₈H₃₂N₂O₂ [ No CAS ]

Reference： [1]Chemical Science,2014,vol. 5,p. 4840 - 4844

62
[ 30483-75-1 ]
C₁₉H₂₄N₂ [ No CAS ]
C₂₉H₃₅N₃O [ No CAS ]

Reference： [1]Chemical Science,2014,vol. 5,p. 4840 - 4844

63
[ 30483-75-1 ]
C₁₈H₂₂N₂O [ No CAS ]
C₂₈H₃₃N₃O₂ [ No CAS ]

Reference： [1]Chemical Science,2014,vol. 5,p. 4840 - 4844

64
[ 30483-75-1 ]
2-chloro-2,2-difluoro-N-(2-methoxyethyl)-N-(4-morpholinophenyl)acetamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 1646 - 1650
Angew. Chem.,2015,vol. 127,p. 1666 - 1670

65
[ 30483-75-1 ]
C₁₅H₁₈F₂N₂O₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 1646 - 1650
Angew. Chem.,2015,vol. 127,p. 1666 - 1670

66
[ 30483-75-1 ]
[ 109-85-3 ]
C₁₃H₂₀N₂O₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 1646 - 1650
Angew. Chem.,2015,vol. 127,p. 1666 - 1670

67
[ 30483-75-1 ]
[ 98-80-6 ]
[ 169963-54-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; acetonitrile; at 20℃; for 18h;Inert atmosphere; Reflux;	General procedure: A suspension of the appropriate amide (1.0 mmol) and pyridine-3-boronic acid (1.1 mmol) were suspended in acetonitrile-aqueous sodium carbonate (1:1, 0.4 M, 10 mL) and deoxygenated with bubbling argon at ambient temperature. A catalytic amount of Pd(PPh3)4(0.05 mmol, 5 mol%) was added, and the mixture heated at reflux for 18 h. The reaction was partitioned between ethyl acetate (30 mL) and saturated aqueous sodium carbonate (30 mL), the layers separated, and the aqueous layer extracted with ethyl acetate (2 × 30 mL). The combined organic extracts were washed with brine (40 mL), dried (MgSO4), filtered, and the solvent evaporated under reduced pressure to give the crude product.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 95,p. 277 - 301

68
[ 30483-75-1 ]
[ 1692-25-7 ]
4-(4-(pyridin-3-yl)phenyl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; acetonitrile; at 20℃; for 18h;Inert atmosphere; Reflux;	General procedure: A suspension of the appropriate amide (1.0 mmol) and pyridine-3-boronic acid (1.1 mmol) were suspended in acetonitrile-aqueous sodium carbonate (1:1, 0.4 M, 10 mL) and deoxygenated with bubbling argon at ambient temperature. A catalytic amount of Pd(PPh3)4(0.05 mmol, 5 mol%) was added, and the mixture heated at reflux for 18 h. The reaction was partitioned between ethyl acetate (30 mL) and saturated aqueous sodium carbonate (30 mL), the layers separated, and the aqueous layer extracted with ethyl acetate (2 × 30 mL). The combined organic extracts were washed with brine (40 mL), dried (MgSO4), filtered, and the solvent evaporated under reduced pressure to give the crude product.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 95,p. 277 - 301

69
[ 30483-75-1 ]
[ 452056-98-3 ]
4-(4-(4-fluorophenyl)-1-methyl-2-(methylthio)-1H-imidazol-5-yl)-N-(4-morpholinophenyl)pyridin-2-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 443 - 456

70
[ 30483-75-1 ]
[ 57260-71-6 ]
tert-butyl 4-(4-morpholinophenyl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 1041 - 1046

71
[ 30483-75-1 ]
4-{4-[4-((5-nitrofuran-2-yl)methyl)piperazin-1-yl]phenyl}morpholine [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 1041 - 1046

72
4-methyl-1,1-diphenylpent-4-en-1-ol [ No CAS ]
[ 30483-75-1 ]
(+)-(S)-4-{4-[(2-methyl-5,5-diphenyltetrahydrofuran-2-yl)methyl]phenyl}morpholine [ No CAS ]
4-{4-[(2-methyl-5,5-diphenyltetrahydrofuran-2-yl)methyl]phenyl}morpholine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 13390 - 13392
Angew. Chem.,2015,vol. 54,p. 13588 - 13590,3

73
[ 30483-75-1 ]
[ 1616980-51-8 ]
(-)-(S)-2-benzyl-5-(tert-butyl)-3-(4-morpholinobenzyl)-1,2,5-thiadiazolidine-1,1-dioxide [ No CAS ]
(-)-(R)-2-benzyl-5-(tert-butyl)-3-(4-morpholinobenzyl)-1,2,5-thiadiazolidine-1,1-dioxide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 5919 - 5922

74
[ 30483-75-1 ]
tert-butyl 4-(((4-(1H-pyrazol-4-yl)pyridin-3-yl)oxy)methyl)piperidine-1-carboxylate [ No CAS ]
C₂₉H₃₇N₅O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 4711 - 4723

75
[ 372-47-4 ]
[ 30483-75-1 ]
4-(4-(3-fluoropyridin-4-yl)phenyl)morpholine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 10463 - 10467
Angew. Chem.,2016,vol. 128,p. 10619 - 10623,5

76
[ 30483-75-1 ]
[ 16872-09-6 ]
C₁₂H₂₃B₁₀NO [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 17542 - 17546

77
[ 30483-75-1 ]
[ 384-64-5 ]
9-(4-bromophenyl)-6-fluoro-7-phenyl-3-oxa-9-azabicyclo[3.3.1]non-6-ene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 2249 - 2254

78
[ 30483-75-1 ]
[ 2524-67-6 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2809 - 2812

79
[ 30483-75-1 ]
[ 109-77-3 ]
C₁₃H₁₃N₃O [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6497 - 6501

80
[ 30483-75-1 ]
[ 75264-92-5 ]
4-(4-((trifluoromethyl)selanyl)phenyl)morpholine [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 3919 - 3922

81
[ 30483-75-1 ]
[ 1351403-44-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1,1,1,2,2,2-hexamethyldisilane; [D3]acetonitrile; potassium methanolate; at 20℃; for 4h;	A mixture of 121 mg of 4- (4-bromophenyl) morpholine (0.5 mmol)And 70.15 mg of potassium methoxide (1 mmol) were dissolved in 1 mL of deuterated acetonitrile, and 200 muL of hexamethyldisilane (1 mmol) was added dropwise to the mixture, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, 10 mL of water was quenched and extracted with 30 mL of ether three times. The organic phase was collected and the solvent was removed under reduced pressure. The residue was purified by column chromatography eluting with petroleum ether: ethyl acetate = 20: 1 (v / v) to give 71 mg of 4- (4-deuterated) morpholine (white solid, 87% yield)

Reference： [1]Patent: CN106928117,2017,A .Location in patent: Paragraph 0086-0088
[2]Journal of the American Chemical Society,2018,vol. 140,p. 10970 - 10974

82
[ 110-91-8 ]
[ 589-87-7 ]
[ 30483-75-1 ]
[ 4096-22-4 ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 2832 - 2846

83
[ 30483-75-1 ]
[ 78-67-1 ]
4-(4-bromophenyl)morpholine-3-carbonitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 12786 - 12790

84
[ 30483-75-1 ]
[ 637-59-2 ]
C₁₉H₂₃NO [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 310 - 313

85
[ 136918-14-4 ]
[ 30483-75-1 ]
C₁₈H₁₈N₂O₃ [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 983 - 986

86
[ 30483-75-1 ]
methyl 2-((2-methoxybenzyl)oxy)-2-(1-(4-morpholinophenyl)-3-oxoisoindolin-1-yl)-2-phenylacetate [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 983 - 986

87
[ 30483-75-1 ]
methyl 2-(5, 6-dimethyl-1-(4-morpholinophenyl)-3-oxoisoindolin-1-yl)-2-((2-methoxybenzyl)oxy)-2-phenylacetate [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 983 - 986

88
[ 30483-75-1 ]
methyl 2-(5, 6-dichloro-1-(4-morpholinophenyl)-3-oxoisoindolin-1-yl)-2-((2-methoxybenzyl)oxy)-2-phenylacetate [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 983 - 986

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
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P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
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P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
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P308	IF exposed or concerned:
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P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
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P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
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P361	Remove/Take off immediately all contaminated clothing.
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P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
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P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 30483-75-1 ] {[proInfo.proName]}

Quality Control of [ 30483-75-1 ]

Related Doc. of [ 30483-75-1 ]

Product Details of [ 30483-75-1 ]

Calculated chemistry of [ 30483-75-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 30483-75-1 ]

Application In Synthesis of [ 30483-75-1 ]

[ 30483-75-1 ] Synthesis Path-Upstream 1~20

[ 30483-75-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 30483-75-1 ]

Aryls

Bromides

Related Parent Nucleus of [ 30483-75-1 ]

Morpholines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 30483-75-1 ]

Related Parent Nucleus of
[ 30483-75-1 ]