[ CAS No. 5392-12-1 ] {[proInfo.proName]}

Name: 5392-12-1|2-Methoxy-1-naphthaldehyde|98%
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Quality Control of [ 5392-12-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 5392-12-1 ]

Product Details of [ 5392-12-1 ]

CAS No. :	5392-12-1	MDL No. :	MFCD00004004
Formula :	C₁₂H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YIQGLTKAOHRZOL-UHFFFAOYSA-N
M.W :	186.21	Pubchem ID :	79352
Synonyms :

Calculated chemistry of [ 5392-12-1 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.08
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	55.83
TPSA :	26.3 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) :	-5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.88
Log Po/w (XLOGP3) :	2.61
Log Po/w (WLOGP) :	2.66
Log Po/w (MLOGP) :	2.11
Log Po/w (SILICOS-IT) :	3.12
Consensus Log Po/w :	2.48

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.04
Solubility :	0.172 mg/ml ; 0.000922 mol/l
Class :	Soluble
Log S (Ali) :	-2.81
Solubility :	0.287 mg/ml ; 0.00154 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.15
Solubility :	0.0132 mg/ml ; 0.0000708 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.08

Safety of [ 5392-12-1 ]

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 [ 5392-12-1 ]

* 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 [ 5392-12-1 ]
Downstream synthetic route of [ 5392-12-1 ]

[ 5392-12-1 ] Synthesis Path-Upstream 1~1

1
[ 5392-12-1 ]
[ 3401-47-6 ]

Reference： [1] ChemCatChem, 2016, vol. 8, # 21, p. 3367 - 3374

[ 5392-12-1 ] Synthesis Path-Downstream 1~85

1
[ 75-52-5 ]
[ 5392-12-1 ]
[ 116272-79-8 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2050 - 2060
[2]Recueil des Travaux Chimiques des Pays-Bas,1988,vol. 107,p. 27 - 39
[3]Chemical Communications,2017,vol. 53,p. 6760 - 6763
[4]Archiv der Pharmazie,1939,vol. 277,p. 359,377, 394
Proceedings of the National Institute of Sciences of India,1940,vol. 6,p. 135,167

2
[ 5392-12-1 ]
[ 316-68-7 ]
[ 2804-85-5 ]

Reference： [1]Journal of Organic Chemistry,1958,vol. 23,p. 542

3
[ 5392-12-1 ]
[ 1071-36-9 ]
[ 42924-45-8 ]

Reference： [1]Journal of the Indian Chemical Society,1959,vol. 36,p. 54

4
[ 5392-12-1 ]
[ 947-62-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium permanganate; In acetone; at 20℃; for 8h;	Dry 2-methoxy-1-naphthalene carbaldehyde The above prepared by reacting 8.5 g (45. 7mmol) was dissolved in 80 ml of Dry acetone was added sodium carbonate solution (4.86 g in 24.3 ml of water) was slowly added in portions of potassium permanganate 10.1 G (63. 9_1), stirred at room temperature for 8 hours. Completion of the reaction, the removal of excess hydrogen peroxide with potassium permanganate, the solution was filtered, with Of acetone and the cake was repeatedly washed with aqueous sodium carbonate solution, the acetone was distilled off, to remove the unreacted starting material extracted with methylene chloride, using conc. Hydrochloric acid, extracted with dichloromethane, dried over anhydrous sodium sulfate, and evaporated to dryness to give a white solid 7.85 g, yield 85%.

Reference： [1]Patent: CN101602750,2016,B .Location in patent: Paragraph 0359; 0360
[2]Bulletin of the Chemical Society of Japan,2003,vol. 76,p. 575 - 585
[3]Bulletin de la Societe Chimique de France,1897,vol. <3> 17,p. 309
[4]Journal of the Chemical Society,1941,p. 687

5
[ 5392-12-1 ]
[ 136402-93-2 ]

Yield	Reaction Conditions	Operation in experiment
		Solid-phase manipulations were performed in polypropylene syringes fitted with a polyethylene porous disc. Solvents and soluble reagents were removed by filtration. 2- methoxynaphthaldehyde (15 equiv) was condensed on a H2N-XAL-MBHA resin (29 mg, 0.7 EPO <DP n="28"/>mmol/g) using TMOF (1 ml) as a solvent and the mixture was stirred overnight under Ar at 25 0C to give the aldimine. The resin was filtered off and washed with TMOF ( 5x1 min.) and dry THF (5x1 min.)- Then the reduction was carried out with LiBH4 (15 equiv, 40 mul) in dry THF under Ar and the mixture was stirred for 5 h at 65 0C to give the corresponding secondary amine. The resin was filtered off and washed several times with THF, H2O, MeOH and DCM. The amine was cleaved from the resin with 5% TFA in DCM for 5 h at 25 0C. The solution was filtered and evaporated under N2 to dryness. ESI-MS: [(M+H)+ca,c 187.2, (M+H)+ exp: 187.7, (M-NH3)+exp: 170.3]. HPLC: tR: 5.4 min, H2O (0.1% TFA) / ACN (0.1 % TFA) 0-100% in 15 min, column C18 X-Terra 15 mum (4.6x10), lambda = 220 / 254 nm.

Reference： [1]Bulletin de la Societe Chimique de France,1954,p. 615,617
[2]Patent: WO2006/61140,2006,A2 .Location in patent: Page/Page column 26; 27

6
[ 93-04-9 ]
[ 93-61-8 ]
[ 5392-12-1 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 4071 - 4076
[2]Tetrahedron,1975,vol. 31,p. 1005 - 1009

7
[ 708-06-5 ]
[ 74-88-4 ]
[ 5392-12-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; at 45℃; for 2h;Inert atmosphere;	To a solution of 2-hydroxynapthaldehyde 1 (3.0 g,17.4 mmol) in anhydrous acetone (30 mL) was addedanhydrous K2CO3 (2.97 g, 21.5 mmol) and methyliodide(5.43 g, 38.2 mmol) and the resulting mixture was heatedto 45 C (bath temperature) under argon for 2 hours. Aftercompletion of the reaction (monitored by TLC), the solventwas removed in vacuo and the residue worked up inthe usual way using ethyl acetate and water to yield thecrude 2-methoxynapthaldehyde (3.0 gm). The crude 2 wasused for the next step without further purification.

Reference： [1]European Journal of Inorganic Chemistry,2016,vol. 2016,p. 3513 - 3523
[2]Bulletin de la Societe Chimique de France,1897,vol. <3> 17,p. 309
[3]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 5775 - 5784

8
[ 5392-12-1 ]
[ 6055-52-3 ]
[ 115294-02-5 ]

Reference： [1]Journal of general chemistry of the USSR,1961,vol. 31,p. 286 - 294
Zhurnal Obshchei Khimii,1961,vol. 31,p. 313 - 323

9
[ 5392-12-1 ]
[ 16000-39-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydroxylamine hydrochloride; dimethyl sulfoxide; for 0.025h;Heating; Microwave irradiation; Green chemistry;	General procedure: Hydroxylamine hydrochloride, 0.55 g (0.72 mmol)was added to a solution of 0.5 g (0.66 mmol) aldehyde1 in 3 mL of DMSO. The reaction mixture wassubjected to microwave irradiation at 180 W (with 15-sintervals) for 60-120 s. Reaction progress was monoredby TLC on aluminum coated silica gel (ethylacetate:hexane, 1 : 4). After the reaction had beencomplete, the reaction mixture was cooled to roomtemperature and poured on crushed ice, the reactionproduct was extracted in ethyl acetate, the extract wasdried over Na2SO4 and concentrated in a vacuum, andthe residue was recrystallized.

Reference： [1]Russian Journal of Organic Chemistry,2019,vol. 55,p. 702 - 706
Zh. Org. Khim.,2019,vol. 55,p. 817
[2]Synthesis,1985,p. 510 - 512
[3]Chemische Berichte,1974,vol. 107,p. 1221 - 1227
[4]Synlett,2002,p. 775 - 777

10
[ 3321-92-4 ]
[ 5392-12-1 ]
(E)-1-(3,5-Dichloro-2-hydroxy-phenyl)-3-(2-methoxy-naphthalen-1-yl)-propenone [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 1115 - 1116

11
[ 926-39-6 ]
[ 5392-12-1 ]
[ 110925-72-9 ]

Reference： [1]Pharmaceutical Chemistry Journal,1987,vol. 21,p. 323 - 326
Khimiko-Farmatsevticheskii Zhurnal,1987,vol. 21,p. 551 - 554

12
[ 5392-12-1 ]
[ 31675-43-1 ]
[ 74552-48-0 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 3994 - 3998

13
[ 5392-12-1 ]
[ 3226-34-4 ]
(E)-1-(3-Chloro-2-hydroxy-phenyl)-3-(2-methoxy-naphthalen-1-yl)-propenone [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 1115 - 1116

14
[ 5392-12-1 ]
[ 28480-70-8 ]
[ 141213-82-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium hydroxide at 60℃; for 16h;

Reference： [1]Subbanwad; Vibhute; Shingare [Journal of the Indian Chemical Society, 1991, vol. 68, # 10, p. 570 - 571]

15
[ 5392-12-1 ]
[ 40137-11-9 ]
[ 76041-83-3 ]

Reference： [1]Zeitschrift fur Chemie,1980,vol. 20,p. 337 - 338

16
[ 5392-12-1 ]
[ 40696-22-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 20℃;	Following a literature procedure,5 sodium borohydride (0.53 g, 14.0 mmol) was added in small portions to a stirred 0 C solution of <strong>[5392-12-1]2-methoxy-1-naphthaldehyde</strong> (5.03 g, 27.0 mmol) in THF (135 mL). Once the addition was complete, the reaction mixture was allowed to warm to rtovernight. Water (135 mL) was added and the mixture was extracted with Et2O (2 × 150 mL). The combined organic layers were washed withbrine (2 × 150 mL) before being dried and evaporated. The crude residue was recrystallised (EtOAc/hexane) to give C (4.59 g, 90%) ascolourless crystals, mp 100-102 C (lit.6 100-101 C). IR: 3326, 2968, 1626, 1594, 1512, 1472, 1249, 1156, 1085, 1059, 984, 803, 741 cm-1. 1HNMR (500 MHz): delta = 8.08 (d, J = 8.5 Hz, 1 H), 7.80 (d, J = 9.0 Hz, 1 H), 7.77 (d, J = 8.5 Hz, 1 H), 7.51-7.48 (m, 1 H), 7.36-7.33 (m, 1 H),7.24 (d, J = 9.0 Hz, 1 H), 5.14 (s, 2 H, CH2), 3.93 (s, 3 H, CH3), 2.19 (br s, 1 H, OH). 13C NMR (125 MHz): delta = 155.0 (C-O), 132.7 (C)), 130.0(CH), 129.0 (C), 128.4 (CH), 126.9 (CH), 123.5 (CH), 122.9 (CH), 121.1 (C), 112.9 (CH), 56.4 (CH3), 55.7 (CH2).

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 5492 - 5495
[2]Synlett,2017,vol. 28,p. 1738 - 1742
[3]Journal of the Chemical Society,1963,p. 3295 - 3308
[4]Journal of the Chemical Society. Perkin transactions I,1980,p. 1986 - 1993
[5]Journal of Medicinal Chemistry,2017,vol. 60,p. 1928 - 1945

17
[ 5392-12-1 ]
[ 753022-59-2 ]

Yield	Reaction Conditions	Operation in experiment
	With selenium(IV) oxide; dihydrogen peroxide; trifluoroacetic acid; In dichloromethane; water; at 20℃; for 4h;	General procedure: Hydrogen peroxide (30%, 10 mL), selenium dioxide (0.1 g) and TFA (1 mL, 12 mmol) were added to a solution of aromatic aldehyde (1 g, 9 mmol) in dichloromethane (10 mL). The biphasic reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was then poured into water and the organic layer separated, washed with water, 10% Na2CO3, again with water, dried over anhydrous Na2SO4 and concentrated to obtain a formyl ester intermediate, which was dissolved as such in methanol (5 mL). This solution was added to 20% methanolic KOH (5 mL) and the resulting dark red solution was refluxed for 1 hour. Excess methyl alcohol was removed under reduced pressure and the residue was acidified using conc. HCl to a light brown solid, which was filtered, dried and recrystallised from alcohol-water to obtain the desired phenols in excellent yields (Table 2).

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9903 - 9909
[2]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 4937 - 4951
[3]Synthesis,1989,p. 167 - 172
[4]Tetrahedron,2001,vol. 57,p. 319 - 329
[5]Journal of Chemical Research,2014,vol. 38,p. 381 - 382

18
[ 5392-12-1 ]
[ 708-06-5 ]

Reference： [1]Journal of Chemical Research, Miniprint,2003,p. 857 - 868
[2]Journal of Chemical Research,2010,p. 222 - 227
[3]Chemistry Letters,2000,p. 738 - 739
[4]Synthetic Communications,1988,vol. 18,p. 191 - 196

19
[ 93-04-9 ]
[ 68-12-2 ]
[ 5392-12-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	With trichlorophosphate; for 5h;	General procedure: A solution of 5 (1 g,6.33 mmol) in dry DMF (5 mL) was cooled to 0 C, and POCl3(2 mL, 21.43 mmol) was added drop-wise. After being stirred at0 C for an hour, the mixture was heated at 95 C for 4 h. The reactionwas quenched with ice-cold water, extracted with ethyl acetate(20 mL 2) and washed with water. Organic phase was driedwith anhydrous Na2SO4 and concentrated in-vacuo to get a residue.The residue was purified by flash column chromatography (ethylacetate-hexane) to get 6 as creamy solid (1.04 g, 88%): mp 80-81 C; IR (KBr) mmax 3019, 2929, 1673, 1607, 1579, 1487, 1384;1H NMR (CDCl3, 300 MHz) d 4.00 (s, 3H), 7.22-7.25 (t, J = 9.0 Hz,1H), 7.39-7.43 (t, J = 6.0 Hz, 1H), 7.59-7.68 (m, 2H), 8.00-8.03 (d,J = 9.0 Hz, 1H), 9.27-9.30 (d, J = 9.0 Hz, 1H), 10.81 (s, 1H); 13CNMR (CDCl3, 75 MHz) d 56.9, 112.9, 116.9, 125.1, 125.3, 128.6,128.9, 130.2, 131.9, 137.9, 164.3, 192.3. Electrospray mass (MeOH)for C12H10O3: 187.1 [M+H]+, 209.2 [M+Na]+, 225.2 [M+K]+.

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 1364 - 1373
[2]Organic Preparations and Procedures International,2004,vol. 36,p. 337 - 340
[3]Journal of the American Chemical Society,2012,vol. 134,p. 5492 - 5495
[4]Tetrahedron,1993,vol. 49,p. 4015 - 4034
[5]Russian Journal of Organic Chemistry,2019,vol. 55,p. 702 - 706
Zh. Org. Khim.,2019,vol. 55,p. 817

20
[ 5392-12-1 ]
[ 4271-96-9 ]
[ 109-94-4 ]
1-methyl-2-<2-(2-methoxynaphthyl)vinyl>-1,4,5,6-tetrahydropyrimidine formate [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1993,vol. 28,p. 979 - 982

21
[ 5392-12-1 ]
[ 74-89-5 ]
[ 76532-34-8 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 140 - 145

22
[ 1438-16-0 ]
[ 5392-12-1 ]
3-Amino-5-[1-(2-methoxy-naphthalen-1-yl)-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 123 - 126

23
[ 5392-12-1 ]
[ 35633-35-3 ]
1-(2-methoxy-4-methyl-1-phenyl)-3-(2-methoxy-1-naphthyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium hydroxide In ethanol; water at 20℃;

Reference： [1]Kar; Lahiri [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 11, p. 1121 - 1124]

24
[ 5392-12-1 ]
[ 1076-26-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 2-methoxy-1-naphthaldehyde With potassium hydroxide; hydrazine hydrate In diethylene glycol for 1.5h; Heating; Stage #2: With pyridine hydrochloride for 0.5h; Heating; Further stages.;
	Multi-step reaction with 2 steps 1: N₂H₄+H₂O; KOH; diethylene glycol

Reference： [1]Gabbutt, Christopher D.; Heron, B. Mark; Instone, Alicia C.; Thomas, David A.; Partington, Steven M.; Hursthouse, Michael B.; Gelbrich, Thomas [European Journal of Organic Chemistry, 2003, # 7, p. 1220 - 1230]
[2]Buu-Hoi; Lavit [Journal of the Chemical Society, 1955, p. 2776,2777]

25
[ 5392-12-1 ]
[ 108-24-7 ]
1,1-diacetoxy-1-(2-methoxynaphth-1-yl)methane [ No CAS ]

Reference： [1]Synthesis,2004,p. 831 - 833
[2]Synthetic Communications,2011,vol. 41,p. 277 - 284
[3]Tetrahedron Letters,2006,vol. 47,p. 5573 - 5576
[4]Tetrahedron,2003,vol. 59,p. 9571 - 9576

26
1,1-diacetoxy-1-(2-methoxynaphth-1-yl)methane [ No CAS ]
[ 5392-12-1 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 9571 - 9576

27
[ 558-13-4 ]
[ 5392-12-1 ]
[ 77295-64-8 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 1151 - 1154
[2]Tetrahedron Letters,2013,vol. 54,p. 512 - 514

28
[ 5392-12-1 ]
[ 88284-48-4 ]
9-(2-methoxy-1-naphthyl)xanthene [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4049 - 4051

29
[ 5392-12-1 ]
[ 1078-28-0 ]
[ 141-43-5 ]
1-(2-Amino-ethyl)-6-methoxy-2-[(E)-2-(2-methoxy-naphthalen-1-yl)-vinyl]-quinolinium [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 6331 - 6335

30
[ 5392-12-1 ]
[ 872-73-1 ]
2-[2-hydroxy-2-(2-methoxy-naphthalen-1-yl)-ethyl]-1-methyl-pyridinium; iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; ethylene glycol

Reference： [1]Rosania, Gustavo R.; Lee, Jae Wook; Ding, Liang; Yoon, Hai-Shin; Chang, Young-Tae [Journal of the American Chemical Society, 2003, vol. 125, # 5, p. 1130 - 1131]

31
[ 5392-12-1 ]
[ 16182-15-3 ]
C₂₁H₂₂N₂O₃S [ No CAS ]

Reference： [1]Antimicrobial Agents and Chemotherapy,2002,vol. 46,p. 2450 - 2457

32
[ 5392-12-1 ]
[ 2751-27-1 ]
C₁₈H₁₅IN₂O₃S [ No CAS ]

Reference： [1]Antimicrobial Agents and Chemotherapy,2002,vol. 46,p. 2450 - 2457

33
[ 5392-12-1 ]
[ 557-20-0 ]
(R)-1-(2-Methoxy-naphthalen-1-yl)-propan-1-ol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 295 - 296

34
[ 5392-12-1 ]
[ 15159-14-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Raney nickel; ethanol / 100 °C / 73550.8 Torr / Hydrogenation 2: CrO₃; water containing acetic acid / <20

Reference： [1]Martin; Robinson [Journal of the Chemical Society, 1943, p. 491,494][Journal of the Chemical Society, 1949, p. 1866,1869]

35
[ 5392-12-1 ]
[ 10441-48-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetic acid anhydride; sodium acetate / Behandeln des entstandenen 2-Phenyl-4-<2-methoxy-naphthyl-⁽¹⁾-methylen>-oxazolons-⁽⁵⁾ mit verd. Natronlauge 2: hydrogen peroxide; acetic acid

Reference： [1]Mauthner [Journal fur praktische Chemie (Leipzig 1954), 1917, vol. <2> 95, p. 60]

36
[ 5392-12-1 ]
[ 156941-54-7 ]

Yield	Reaction Conditions	Operation in experiment
		While cooling on ice, 0.61 g of potassium t-butoxide was added to 20 ml of a tetrahydrofuran suspension containing 2.28 g of (methoxymethyl)triphenylphosphonium chloride under nitrogen atmosphere. The obtained mixture was stirred for 5 minutes. Thereafter, 600 mg of <strong>[5392-12-1]2-methoxy-1-naphthaldehyde</strong> was added to the reaction solution while cooling on ice. The obtained mixture was stirred at the same temperature for 20 minutes. The reaction solution was diluted with ethyl acetate, and then washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 667 mg of 2-methoxy-1-(2-methoxyvinyl)naphthalene containing a small amount of triphenylphosphine. This compound was used in the next reaction without further purification.

Reference： [1]Patent: US2005/256103,2005,A1 .Location in patent: Page/Page column 78

37
[ 5392-12-1 ]
[ 77295-64-8 ]

Yield	Reaction Conditions	Operation in experiment
		Triphenylphosphine (2.82 g, 10.75 mmol) and carbon tetrabromide (1.78 g, 5.37 mmol) were dissolved in CH2Cl2 (22 niL) and stirred for 5 minutes at 0 C. A CH2Cl2 (5 mL) solution of 2-methoxy-l-naphthaldehyde was added EPO <DP n="19"/>and the resulting solution stirred at 0 0C for 15 minutes then quenched with Na2CO3 (25 mL, sat. aq.) and diluted with CH2Cl2 (25 mL). The aq layer was extracted with CH2Cl2 (15 mL). The combined CH2Cl2 layers were washed with H2O (25 mL), sat aq NaCl (25 mL), dried over Na2SO4, decanted and concentrated. The resulting solid was triturated with 5% Et2O- hexanes and filtered. The filtrate was concentrated to give the desired product, which was used in the next step without further purification.

Reference： [1]Patent: WO2006/71750,2006,A1 .Location in patent: Page/Page column 17-18

38
[ 5392-12-1 ]
ethyl 2-carbethoxy-3-(2-methoxy-1-naphthyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride;piperidine; diethyl malonate; In benzene;	Step A Diethyl2-[(2-methoxy-1-naphthyl)methylene]malonate 2-Methoxy-1-naphthaldehyde (25 g, 1.34.10-1 mol) in benzene (200 ml) is heated for 20 hours at reflux in the presence of diethyl malonate (25 ml, 1.65.10-1 mol, 1.23 eq.) and piperidine (2 ml, 2.02.10-2 mol, 0.15 eq.) in a Dean-Stark apparatus. After adding a few additional drops of piperidine, the mixture is returned to reflux for 20 hours. The reaction mixture is diluted with toluene (200 ml) and washed with water (125 ml). After separation of the phases, the organic phase is treated with a 1N hydrochloric acid solution (190 ml), then with a saturated NaHCO3 solution (125 ml) and with a saturated NaCl solution (125 ml). After drying over MgSO4 and evaporation under reduced pressure, the oil obtained is recrystallized from cyclohexane. Melting point: 86 C.; Elemental microanalysis:

Reference： [1]Patent: US6423870,2002,B1

39
[ 5392-12-1 ]
[ 67367-39-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; water;	STAGE A: (2-METHOXY-1-NAPHTHYL)METHYL CHLORIDE STR72 Procedure To a suspension of lithium aluminum hydride (96.66 mmol; 3.69 g; 3 eq.) in anhydrous tetrahydrofuran (THF) is added dropwise, at 0 C. and under argon, a solution of <strong>[5392-12-1](2-methoxy-1-naphthyl)carbaldehyde</strong> (32.22 mmol; 6 g) in 30 cm3 of the same solvent. Stirring is maintained overnight at room temperature. The mixture is hydrolyzed by slow addition, at 0 C., of 4 cm3 of water followed by 4 cm3 of 15% NaOH solution and finally 12 cm3 of water. The precipitate formed is filtered off; the filtrate is dried over MgSO4 and then evaporated. 2-(2-Methoxy-1-naphthyl)nethanol, which is pure by NMR, is isolated. The alcohol thus obtained (30.28 mmol; 5.7 g) is dissolved in 80 cm3 of anhydrous toluene in the presence of pyridine (30.28 mmol; 2.5 cm3).

Reference： [1]Patent: US5712312,1998,A
[2]Journal of the American Chemical Society,2012,vol. 134,p. 5492 - 5495

40
[ 5392-12-1 ]
[ 116272-79-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrogenchloride; sodium hydroxide; In methanol; nitromethane;	EXAMPLE 7 1-(2-methoxynaphth-1-yl)-2-nitroethene (X, (A), R=CH3, R2 =H, n=1) A mixture of <strong>[5392-12-1]2-methoxy-1-naphthaldehyde</strong> (1862 mg, 10 mmol) and nitromethane (610 mg, 10 mmol) in methanol (200 ml) is stirred at room temperature until the solids dissolved. The solution is cooled to about 0 C. and a 30% NaOH solution (2 ml, 20 mmol) is added dropwise over 30 min. The resulting solution is added slowly at 60 C. to a 35% HCl solution (200 ml). The amorphous solid that formed is filtered and washed with water. The crude product is recrystallized from ethanol to give pure title compound in 80% yield (1835 mg). C13 H11 NO3 requires: C 68.11 H 4.89 H 6.11. found: C 68.05 H 4.79 N 5.99. MS m/z: 229. IR (KBr): 3120, 1620, 1500, 1350 cm-1.

Reference： [1]Patent: US5122537,1992,A

41
[ 5392-12-1 ]
potassium 2-naphthyltrifluoroborate [ No CAS ]
[ 1061653-03-9 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7800 - 7802

42
[ 5392-12-1 ]
[ 166328-07-0 ]
[ 1061653-09-5 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7800 - 7802

43
[ 5392-12-1 ]
potassium o-tolyltrifluoroborate [ No CAS ]
[ 14344-01-5 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7800 - 7802

44
[ 5392-12-1 ]
potassium 2,6-dimethylphenyltrifluoroborate [ No CAS ]
[ 1061653-10-8 ]
[ 1061653-21-1 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7800 - 7802

45
[ 5392-12-1 ]
[ 17577-28-5 ]
[ 858438-29-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: (ethoxycarbonylmethyl)triphenylphosphonium chloride With sodium hydride In tetrahydrofuran; mineral oil for 1h; Inert atmosphere; Reflux; Stage #2: 2-methoxy-1-naphthaldehyde In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Stage #3: With sulfuric acid In acetone for 6h; Reflux;

Reference： [1]Location in patent: experimental part Voelker, Troy; Xia, Haiji; Fandrick, Keith; Johnson, Robert; Janowsky, Aaron; Cashman, John R. [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 5, p. 2047 - 2068]

46
[ 5392-12-1 ]
[ 57260-71-6 ]
[ 1316696-77-1 ]

Yield	Reaction Conditions	Operation in experiment
77%		10,0 g (53,7 mmol) 2-methoxynaphtaldehyde is dissolved in 100 ml dichloromethane . 10,1 g (53,7 mmol) 1-Boc-piperazine is added at room temperature and the mixture is stirred for 10 min. Then 14,8 g (69,8 mmol) sodium triacetoxyborohydride is added into the reaction mixture in small doses using strong stirring (exothermic reaction) at room temperature and the mixture is stirred for 3 hours at room temperature. The reaction is followed by TLC and after completion of the reaction, 100 ml saturated NaHC03 solution and 100 ml MTBE are added. After 15 min stirring, the organic phase is separated and is washed with 1x100 ml saturated NaHC03 solution then with 1x100 ml water, then it is dried on anhydrous Na2S04 and evaporated. The raw product is crystallized from 50 ml iso- propanol .Yield: 14,76 g (77 %) white, crystalline product.TLC: Rf=0,75 (CHC13:MeOH 95:5)

Reference： [1]Patent: WO2011/89456,2011,A1 .Location in patent: Page/Page column 15; 26

47
[ 5392-12-1 ]
[ 32111-21-0 ]
(R)-(2-methoxy-1-naphthyl)(pyrazin-2-yl)methanol [ No CAS ]
[ 1416473-71-6 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: In a Schlenk tube, flushed under argon, (R,R)-TADDOL (0.340 g, 0.728 mmol, 1.0 equiv) was dissolved in anhydrous toluene (C = 0.08 M). Next, n-BuLi (1.4 M in hexanes, 2.0 equiv) was slowly added at 10 C. After stirring at this temperature for 20 min, n-BuMgCl (2.0 M in THF, 1.0 equiv) was added at 10 C and the resulting solution was stirred for additional 20 min at the same temperature. n-BuLi (1.4 M in hexanes, 1.0 equiv) was added at 10 C and the mixture was stirred for 20 min at 10 C. 2-Iodopyrazine (0.150 g, 1.0 equiv) was then added at 30 C. The mixture was stirred for 1 h between 30 and 10 C. The reaction was monitored by TLC (eluent: ethyl acetate/cyclohexane 8/2). The medium was then cooled to 100 C and the aldehyde (1.82 mmol, 2.5 equiv) was added. The mixture was left at 100 C and stirred for 2 h. The reaction was quenched with a saturated aqueous solution of NH4Cl. The aqueous layer was extracted with ethyl acetate and acidified (pH = 3-4) using a sulphuric acid aqueous solution. The aqueous solution was then extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The crude product was then purified by column chromatography over silica gel and analysed by chiral GC to determine enantiomeric ratios.

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 1678 - 1682

48
[ 5392-12-1 ]
[ 1407709-18-5 ]
[ 1407708-91-1 ]

Yield	Reaction Conditions	Operation in experiment
68%	With 2,3-diazobicyclo[2.2.1]heptane bis-hydrochloride; In 1,2-dichloro-ethane; at 90℃; for 24h;	To hydrazine 11 .2HCl (2.6 mg, 0.015 mmol, 0.1 equivalent), a solution of 2-methoxynapthaldehyde (55.9 mg, 0.3 mmol, 2 equivalents) was added in 0.5 ml DCE, followed by a solution of dimethyl cyclopropene-1,1-dicarboxylate (42 mg, 0.15 mmol, 1 equivalent) in 0.25 ml DCE. The reaction was heated to 90C for 24 hours. Upon cooling to room temperature, the reaction mixture was diluted with DCM, washed with 1 M NaOH, extracted into DCM, dried with sodium sulfate, and concentrated. The product was purified by column chromatography on Silica (5% EtOAc/hex) to yield the compound as a yellow oil (38 mg, 0.1 mmol, 68% yield). 1 H NMR (300 MHz, CDCl3) delta 9.71 (s, 1H), 7.99 (d, 1H, J=8.6), 7.79 (m, 2H), 7.45 (m, 1H), 7.34 (m, 1H), 7.25 (m, 1H), 6.93 (d, 1H, J=17 Hz), 6.05 (d, 1H, J=17 Hz), 4.59 (dd, 4H, J=11.4 Hz), 3.92 (s, 3H), 2.09 (s, 6H); 13C NMR (CDCl3): 197.76, 170.73, 154.65, 132.29, 129.80, 129.22, 128.74, 128.59, 127.97, 126.98, 123.75, 123.62, 119.07, 113.09, 63.16, 56.64, 56.41 , 20.86; LRMS (APCI+) exact mass calculated for C21H22O6+ (MH+) requires m/z 371.14, found m/z 371.17

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 18581 - 18584
[2]Patent: WO2014/22454,2014,A1 .Location in patent: Paragraph 099; 0174

49
[ 5392-12-1 ]
[ 1263324-44-2 ]
[ 1407708-94-4 ]

Yield	Reaction Conditions	Operation in experiment
79%	With 2,3-diazobicyclo[2.2.1]heptane bis-hydrochloride; In 1,2-dichloro-ethane; at 90℃; for 24h;	To hydrazine 11.2HCl (2.6 mg, 0.015 mmol, 0.1 equivalent), a solution of 2-methoxynapthaldehyde (55.9 mg, 0.3 mmol, 2 equivalents) was added in 0.5 ml DCE, followed by a solution of ((cycloprop-2-ene-1,1-diylbis(methylene))bis(oxy))bis(tert-butyldiphenylsilane) (87 mg, 0.15 mmol, 1 equivalent) in 0.25 ml DCE. The reaction was heated to 90C for 24 hours. Upon cooling to room temperature, the reaction mixture was diluted with DCM, washed with 1 M NaOH, extracted into DCM, dried with sodium sulfate, and concentrated. The product was purified by column chromatography on Silica (2% EtOAc/hex) to yield the compound as an oil (90 mg, 0.12 mmol, 79% yield). 1H NMR (300 MHz, CDCl3) delta 9.78 (s, 1H), 8.07 (m, 1 H), 7.71 -7.65 (m, 10H), 7.50-7.25 (m, 15H), 6.85 (d, 1 H, J=17Hz), 6.22 (d, 1 H, J=17Hz), 4.28 (s, 4H), 3.84 (s, 3H), 1 .08 (s, 18H). 13C NMR (CDCl3): 201 .85, 154.52, 135.87, 135.83, 133.23, 133.20, 132.44, 131 .17, 129.89, 129.83, 129.30, 129.15, 128.36, 127.88, 127.85, 127.00, 126.69, 124.31 , 123.59, 120.03, 1 13.14, 64.10, 60.75, 56.32, 27.03, 19.48. LRMS (APCI+) exact mass calculated for C49H54O4Si2+ (MH+) requires m/z 762.36, found m/z 763.76

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 18581 - 18584
[2]Patent: WO2014/22454,2014,A1 .Location in patent: Paragraph 099; 0175

50
[ 5392-12-1 ]
[ 1407709-21-0 ]
[ 1407708-97-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	With 2,3-diazobicyclo[2.2.1]heptane bis-hydrochloride; In 1,2-dichloro-ethane; at 90℃; for 24h;	To hydrazine 11 2HCI (0.5 mg, 0.003 mmol, 0.1 equivalent) and (cycloprop-2-ene-1 ,1 -diylbis(methylene))bis((4-bromophenyl)sulfane) (1 1 mg, 0.025 mmol, 1 equivalent), a solution of 2-methoxynapthaldehyde (9.3 mg, 0.05 mmol, 2 equivalents) was added in 0.13 ml DCE. The reaction was heated to 90C for 24 hours. Upon cooling to room temperature, the reaction mixture was diluted with DCM, washed with 1 M NaOH, extracted into DCM, dried with sodium sulfate, and concentrated. The residue was purified by column chromatography on Si (1 % EtOAc/hex) to yield the product (8 mg, 0.012 mmol, 50 % yield). 1 H NMR (300 MHz, CDCl3) delta 9.58 (s, 1H), 8.07 (d, 1 H, J=9Hz), 7.80 (m, 2H), 7.48-7.25 (m, 1 1 H), 6.96 (d, 1 H, J=17), 6.16 (d, 1 H, J=17Hz), 3.94 (s, 3H), 3.62 (dd, 4H, J=13Hz). 13C NMR (CDCl3): 198.22, 154.75, 135.31 , 132.35, 132.20, 132.02, 131 .92, 129.85, 129.28, 128.57, 128.23, 127.04, 123.89, 123.80, 120.93, 1 19.03, 1 13.20, 58.34, 56.56, 38.31 . LRMS (APCI+) exact mass calculated for C29H24Br2O2S2+ (MH+) requires m/z 628.44, found m/z 629.66

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 18581 - 18584
[2]Patent: WO2014/22454,2014,A1 .Location in patent: Paragraph 099; 0177

51
[ 5392-12-1 ]
[ 1263324-41-9 ]
[ 1407708-79-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With 2,3-diazobicyclo[2.2.1]heptane bis-hydrochloride; In 1,2-dichloro-ethane; at 90℃; for 6h;	To hydrazine 11 .2HCl (2.6 mg, 0.015 mmol, 0.1 equivalent), a solution of 2-methoxy-1 -napthaldehyde (55.9 mg, 0.3 mmol, 2 equivalents) was added in 0.5 ml DCE, followed by a solution of cyclopropene 10 (42 mg, 0.15 mmol, 1 equivalent) in 0.25 ml DCE. The reaction was heated to 90C for 6 hours. Upon cooling to room temperature, the reaction mixture was diluted with DCM, washed with 1 M NaOH, extracted into DCM, dried with sodium sulfate, and concentrated. The product was purified by column chromatography on Si (5% EtOAc/hex) to yield the compound as a yellow oil (47.6 mg, 0.102 mmol, 68% yield). 1H NMR (300 MHz, CDCl3) delta 9.75 (s, 1 H), 8.08 (m, 1 H), 7.53 (m, 2 H), 7.20-7.38 (m, 13 H), 6.87 (d, 1 H, J=16.8 Hz), 6.15 (d, 1 H, J=16.8 Hz), 4.59 (s, 4 H), 3.99 (dd, 4 H, J=7.8 Hz), 3.87 (s, 3 H); 13C NMR (CDCl3, 75 MHz): 99.86, 91 .34, 88.37, 87.31 , 87.04, 86.73, 86.70, 86.57, 86.55, 86.43, 86.41 , 86.27, 86.24, 85.81 , 85.68, 85.07, 83.79, 76.53, 75.91 , 73.76, 73.37; LRMS (APCI+) exact mass calculated for C31H31O4+ (MH+) requires m/z 467.21 , found m/z 465.9

Reference： [1]Patent: WO2014/22454,2014,A1 .Location in patent: Paragraph 099; 0170

52
[ 5392-12-1 ]
[ 1554689-44-9 ]
[ 1554689-36-9 ]

Yield	Reaction Conditions	Operation in experiment
12%	With 2,3-diazobicyclo[2.2.1]heptane bis-hydrochloride; In 1,2-dichloro-ethane; at 90℃; for 6h;	To hydrazine 11 2HCI (2.6 mg, 0.015 mmol, 0.1 equivalent), a solution of 2- methoxynapthaldehyde (55.9 mg, 0.3 mmol, 2 equivalents) was added in 0.5 ml DCE, followed by a solution of 3,3-bis((allyloxy)methyl)cycloprop-1 -ene (27 mg, 0.15 mmol, 1 equivalent) in 0.25 ml DCE. The reaction was heated to 90C for 6 hours. Upon cooling to room temperature, the reaction mixture was diluted with DCM, washed with 1 M NaOH, extracted into DCM, dried with sodium sulfate, and concentrated. The yield was determined with an NMR standard. 1H NMR (300 MHz, CDCl3) 5 9.78 (s, 1 H), 6.89 (d, 1 H, J=17.1 Hz), 6.16 (d, 1 H, J=16.8Hz)

Reference： [1]Patent: WO2014/22454,2014,A1 .Location in patent: Paragraph 099; 0176

53
[ 5392-12-1 ]
[ 67-64-1 ]
[ 1609567-99-8 ]

Yield	Reaction Conditions	Operation in experiment
70%		General procedure: To a flame-dried flask equipped with a magnetic stir bar was added(S)-proline (6.9 mg, 0.06 mmol) and P-4a (1.2 mg, 0.002 mmol), which was followed by injection of anhydrous acetone(0.6 mL) and anhydrous DMSO (0.2 mL). After the mixture was stirred for 30 min in an ice bath, aldehyde (0.2 mmol)was added. The reaction mixture was stirred at 0 oC for 48 hours, and then quenched with a few drops of saturatedNH4Cl solution. The mixture was extracted with ethyl acetate (5 mL × 3). The organic layer was combined, dried overMgSO4, and concentrated under reduced pressure. The crude product was separated by flash column chromatographywith ethyl acetate and petroleum ether (1:3, v/v) as eluent to give the target product. (4R)-Hydroxy-4-(9-anthranyl)-butan-2-one 3a. Yellow solid, yield: 83%, enantiomeric excess: 99%, HPLC analysis:Daicel Chiralpak OD-H, hexane/iso-propanol = 95:5 (v/v), flow rate = 1.0 mL/min, lambda= 254 nm, retention time: 29.38min (minor) and 50.28 min (major). The physical data are identical to those previously reported
60%		General procedure: (S)-proline (2.5 mg, 0.025 mmol, 0.05 equiv) was added to a mixture of dry DMSO (250 L), dry CHCl3 (250 L) and dry acetone (750 L) and stirred for 30 min in a sealed vessel at 0C. The corresponding aromatic aldehyde (0.5 mmol, 1 equiv) was added and the mixture was stirred for an additional 4 d at 0C. After this time the mixture was diluted with water (5 mL) and ethyl acetate (5mL) and partitioned. The aqueous layer was washed with ethyl acetate (5 mL x 3), and the combined organic layers were dried over Na2SO4. Evaporation of the solvent and flash column chromatography with the specified solvent system afforded the desired product.

Reference： [1]Chinese Chemical Letters,2018,vol. 29,p. 1223 - 1225
[2]Synlett,2014,vol. 25,p. 961 - 964

54
[ 5392-12-1 ]
[ 1606-67-3 ]
[ 1613255-76-7 ]

Yield	Reaction Conditions	Operation in experiment
48%	In ethanol; at 20℃; for 12h;	General procedure: To a stirred solution of 1-aminopyrene (4) (0.20g, 0.92mmol) in ethanol (10ml), 2-hydroxy-1-naphthaldehyde (5) (0.16g, 0.95mmol) was added at room temperature. The reaction mixture was stirred for 12h. After that, the solid residue was filtered off. The resulting precipitate was collected and the crude product was further washed with ethanol several times to afford the pure product 1. Yield: 0.17g (51%).

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2014,vol. 130,p. 7 - 12

55
[ 5392-12-1 ]
[ 1616063-59-2 ]
[ 1642586-92-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	In acetic acid; for 4h;Reflux;	General procedure: A mixture of 5 (4.17 g, 0.01 mol) and aromatic aldehydes (0.01 mol.) in glacial acetic acid (20 mL) was refluxed for 4 h. The reaction mixture was cooled, filtered and the obtained solid was recrystallized from dioxane to give 7am, respectively.

Reference： [1]Acta poloniae pharmaceutica,2014,vol. 71,p. 603 - 614

56
[ 5392-12-1 ]
(3-(bis(trimethylsilyl)amino)phenyl)magnesium bromide [ No CAS ]
(3-amino-phenyl)-(2-methoxy-naphthalen-1-yl)-methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In tetrahydrofuran; at 0 - 20℃; for 14h;	To a stirred solution of 2-Methoxy-naphthalene-l-carbaldehyde (51a) (1.2 g, 10rnmol) in tetrahydrofuran (5 rnL) was added (3- (bis(trimethylsilyl)amino)phenyl)magnesium chloride (49c) (12.00 mL, 12.00 mmoi) at 0C. The reaction was stirred for 14 h at room temperature, quenched by adding 2 N 1-ICI(12.50 mL) and stirred for 6 h. The reaction mixture was nuetralized with 2 N NaOH (15mL) and extracted with ethyl acetate (2 x 50 mL). The organic layers were combined washed with brine (50 mL). dried over anhydrous MgSO4, filtered and concentrated in vacuum to dryness. The crude residue obtained was purified by flash column chromatography (silica gel 40 g, eluting with 0-100% ethyl acetate in hexane) to furnish (3-arnino-phenyl)-(4-methoxy-naphthalen-i-yl)-methanoi (Sib) (1.7 g, 94% yield) as a whitesolid; ?H NMR (300 MHz, .DMSO-d6) oe 8.26 - 8.18 (m, I H), 7.86 (d, J = 9.0 Hz, I H), 7.81- 7.74 (m, IH), 7.48 (d, .1 = 9.1 Hz, 1H), 7.29 - 7.16 (m, 2H), 6.86 (t, .1 = 7.7 Hz, 1 H), 6.67-6.60(m, IH),6.56(dt,J2.3, 1.2Hz, IH),6.49(dq,J= 7.7, 1.1 Hz, IH),6.31 (ddt,.J=7.8, 2.0, 0.9 Hz, I H), 5.82 (d, J = 4.6 Hz, 1K), 4.90 (s, 21-1), 3.96 (s, 3H); MS (ES±) 302.2(M+Na), MS (ES-) 557.2 (2M-I).

Reference： [1]Patent: WO2015/134998,2015,A1 .Location in patent: Page/Page column 265; 266

57
[ 5392-12-1 ]
(3-(bis(trimethylsilyl)amino)-4-fluorophenyl)magnesium bromide [ No CAS ]
(3-amino-4-fluorophenyl)(2-methoxynaphthalen-1-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.3%		To a stirred solution of 2-methoxy-.I-naphthaldehyde (51.a) (24.21 g, 130 mmol) intetrahydrofuran (100 mL) was added (3-(bis(trimethylsilyl)arnino)-4-fluorophenyl)magnesium bromide (52c) (130 rnL, 130 mmol) at 0C. The reaction was stirred for 20 h at room temperature and quenched by adding hydrogen chloride (2N) (I 63 rnL, 325 mrnol), stirred for 1 h, TLC analysis (ethyl acetate/hexanes, 3/7, v/v) shows reaction was complete. The reaction mixture was treated with sodium hydroxide (2N) (195 mL, 390 rnmol) and extracted with ethyl acetate (2 x 750 mL). The organic layers were combined dried over anhydrous MgSO4, filtered, and evaporated to dryness. The crude residue was purified by flash column chromatography (silica gel 1 .3 kg, eluting with 0-70% ethyl acetate in hexane) to furnish (3-am ino-4-fluorophenyl)(2-methoxynaphthalen- 1- yl)niethanol (61a) (24.84 g, 84 mmol, 64.3 % yield) as a yellow solid; ?H NMR (300 MHz,DMSO-d6) 8.28 - 8.10 (rn, 11-1), 7.87 (d, .1 = 9.0 Hz, I H), 7.84 - 7.72 (m, I H), 7.48 (d, .1 =9.1 Hz, IH), 7.35-7.17 (m, 2H), 6.91 -6.70 (m, 2H), 6.66-6.57 (iii, IH), 6.46 (dddd,.J8.2, 4.6, 2.2, 1.0 Hz, I K), 5.91 (d, .1 = 4.6 Hz, I H, D20 exchangeable), 4.98 (s, 2H, D20exchangeable), 3.96 (s, 3H); ?9FNMR (282 MHz, DMSO-d6) -139.08; MS (ES): MS(ES+) 320.2 (M+Na), MS (ES-) 296.0 (M- 1).

Reference： [1]Patent: WO2015/134998,2015,A1 .Location in patent: Page/Page column 300; 301

58
[ 59576-26-0 ]
[ 5392-12-1 ]
(E)-3-(2-methoxynaphthalen-1-yl)-1-(4-methylpyridin-2-yl)prop-2-en-1-one [ No CAS ]