[ CAS No. 117902-15-5 ] {[proInfo.proName]}

Name: 117902-15-5|4-Fluoro-3-methoxyphenol|97%
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Quality Control of [ 117902-15-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 117902-15-5 ]

CAS No. :	117902-15-5	MDL No. :	MFCD10698649
Formula :	C₇H₇FO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WZUOZXFYRZFFEW-UHFFFAOYSA-N
M.W :	142.13	Pubchem ID :	14118956
Synonyms :

Calculated chemistry of [ 117902-15-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	34.92
TPSA :	29.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.55
Log Po/w (XLOGP3) :	0.93
Log Po/w (WLOGP) :	1.96
Log Po/w (MLOGP) :	1.58
Log Po/w (SILICOS-IT) :	1.76
Consensus Log Po/w :	1.56

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.69
Solubility :	2.93 mg/ml ; 0.0206 mol/l
Class :	Very soluble
Log S (Ali) :	-1.13
Solubility :	10.4 mg/ml ; 0.0733 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.2
Solubility :	0.889 mg/ml ; 0.00625 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.36

Safety of [ 117902-15-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 117902-15-5 ]

* 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 [ 117902-15-5 ]
Downstream synthetic route of [ 117902-15-5 ]

[ 117902-15-5 ] Synthesis Path-Upstream 1~10

1
[ 17715-70-7 ]
[ 103068-41-3 ]
[ 117902-16-6 ]
[ 117902-15-5 ]

Reference： [1] Canadian Journal of Chemistry, 1988, vol. 66, p. 1479 - 1482

2
[ 1360807-54-0 ]
[ 117902-15-5 ]

Reference： [1] Patent: WO2012/27134, 2012, A1, . Location in patent: Page/Page column 2; 3; 4

3
[ 128495-46-5 ]
[ 117902-15-5 ]

Yield	Reaction Conditions	Operation in experiment
35%	Stage #1: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 21 h; Stage #2: With triethylamine In methanol for 18 h;	Intermediate 104-fluoro-3-(methyloxy)phenolTo a solution of 4-fluoro-3-(methyloxy)benzaldehide (1.54 g, 10 mmol) in DCM (30 mL) metachloroperbenzoic acid (2.59 g, 15 mmol) was added portionwise and the reaction mixture was stirred for 3 hours at room temperature. A second portion of m-CPBA (2.59 g, 15 mmol) wasadded and the reaction mixture was stirred for further 18 hrs. The mixture was diluted with DCM (100 mL), washed with an aqueous saturated solution of Na25203 (2x100 mL) and then with an aqueous saturated solution of NaHCO3(50 mL), dried over Na2SO4 and concentrated in vacuo to yield a yellow gum, which was re-dissolved in MeOH (20 mL) and Triethylamine (0.1 ml) was added. The reaction mixture was stirred for 18 hrs at room temperature and concentrated in vacuo. The residue was re-dissolved in Et20 (100 mL) and extracted with an aqueous iN solution of NaOH (50 mL). The aqueous layer was acidified with aqueous 2N HCIto pH=1 and extracted with Et20 (2x50 mL). The combined organic layers were dried overNa2SO4 and concentrated in vacuo to afford the title compound (830 mg, yield: 35percent).1HNMR (400 MHz, CDCI3): 6 ppm 6.81-6.85 (1H, t), 6.40-6.43 (1H, m), 6.21-6.24 (1H, m), 4.61(1H, s), 3.76 (3H, s).

Reference： [1] Patent: WO2013/175215, 2013, A1, . Location in patent: Page/Page column 70 ; 71

4
[ 64465-53-8 ]
[ 117902-15-5 ]

Yield	Reaction Conditions	Operation in experiment
46.7%	at 0 - 100℃; for 0.5 h;	To a suspension of compound 202 (4.0 g, 28.0 mmol) in 30 percent sulfuric acid (15mL) was added sodium nitrite (2.15 g, 31.0 mmol) at 0 °C. The reaction was stirred at 0 °Cfor 20 minutes, and then was added to 60percent sulfuric acid (15 mL) at 100 °C and stirred for 30mm. The reaction mixture was neutralized with anhydrous NaHCO3 and extracted with ethylacetate. The organic layer was washed with water and brine, dried over anhydrous sodiumsulfate and evaporated in vacuo. The crude product was purified by column chromatography(hexanes/dichloromethane: 3/1) to afford the title compound 203 (1.84 g, 46.7 percent yield) as acolorless oil. ‘HNIVIR(400 1VIHz, DMSO-d6): 3.76 (s, 3H), 6.24-6.27 (m, 1H), 6.51 (dd, J 6.8, 2.8 Hz, 1H), 6.96 (dd, J 11.2, 8.4 Hz, 1H), 9.36 (s, 1H).

Reference： [1] Patent: WO2017/132928, 2017, A1, . Location in patent: Paragraph 000102

5
[ 854778-31-7 ]
[ 117902-15-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 8, p. 3522 - 3533

6
[ 2713-33-9 ]
[ 117902-15-5 ]

Reference： [1] Patent: WO2012/27134, 2012, A1,

7
[ 947279-22-3 ]
[ 117902-15-5 ]

Reference： [1] Patent: WO2012/27134, 2012, A1,

8
[ 151-10-0 ]
[ 117902-15-5 ]

Reference： [1] Canadian Journal of Chemistry, 1988, vol. 66, p. 1479 - 1482

9
[ 454-16-0 ]
[ 117902-15-5 ]

Reference： [1] Patent: WO2017/132928, 2017, A1,

10
[ 17715-70-7 ]
[ 103068-41-3 ]
[ 117902-16-6 ]
[ 117902-15-5 ]

Reference： [1] Canadian Journal of Chemistry, 1988, vol. 66, p. 1479 - 1482

[ 117902-15-5 ] Synthesis Path-Downstream 1~77

1
[ 17715-70-7 ]
[ 103068-41-3 ]
[ 117902-16-6 ]
[ 117902-15-5 ]

Reference： [1]Canadian Journal of Chemistry,1988,vol. 66,p. 1479 - 1482

2
[ 151-10-0 ]
[ 117902-15-5 ]

Reference： [1]Canadian Journal of Chemistry,1988,vol. 66,p. 1479 - 1482

4
[ 1194-02-1 ]
[ 117902-15-5 ]
[ 935254-92-5 ]

Yield	Reaction Conditions	Operation in experiment
70%		EXAMPLE 7; 8-fluoro-7-methoxydibenzo[b,d]furan-2-carbonitrile; A. 4-(4-fluoro-3-methoxyphenoxy)benzonitrile; This compound was prepared according to the method of Sawyer, et al. (Sawyer, J. Scott; Schmittling, Elisabeth A.; Palkowitz, Jayne A.; Smith, William J., III. Journal of Organic Chemistry (1998), 63(18), 6338-6343) from <strong>[117902-15-5]4-fluoro-3-methoxyphenol</strong> (Belanger, Patrice C.; Lau, C. K.; Williams, Haydn W. R.; Dufresne, C.; Scheigetz, John. Canadian Journal of Chemistry (1988), 66(6), 1479-82) (9.71 g, 68.3 mmol) and 4-fluorobenzonitrile (8.27 g, 68.3 mmol), which provided 4-(4-fluoro-3-methoxyphenoxy)benzonitrile (11.69 g, 70percent) as an orange oil.

Reference： [1]Patent: US2007/93548,2007,A1 .Location in patent: Page/Page column 8

5
[ 2713-33-9 ]
[ 117902-15-5 ]

Reference： [1]Patent: WO2012/27134,2012,A1

6
[ 947279-22-3 ]
[ 117902-15-5 ]

Reference： [1]Patent: WO2012/27134,2012,A1

7
[ 1360807-54-0 ]
[ 117902-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In ethanol; at 50℃; under 2585.81 Torr; for 5h;	(i) At ambient temperature, 2-butanone (500 ml) and potassium carbonate (108.22 g) were loaded into a flask.(ii) The mixture was heated at 50 °C.(iii) 3, 4-difluorophenol (100 g) diluted in 2-butanone (100 ml) was slowly added.(iv) The mixture was stirred for 15 min.(v) Benzyl bromide (134.05 g) was added.(vi) The mixture was heated under reflux for 3 h. (vii) The mixture was cooled down to ambient temperature.(viii) Water (372 ml) was added.<ix) The mixture was stirred and a phase cut (organic phase up) was conducted.(x) The organic layer was washed with water (100 ml) and a phase cut (organic phase up) was conducted.(xi) 2-butanone was distilled from the organic layer and toluene (175 mi) and NMP (43.75 ml) were added (Mixture A).(xii) Toluene (350 ml) and NMP (87.5 mi) were loaded into a reactor.(xiii) This mixture was stirred and heated at 40 °C.(xiv) Methanol (36.3 ml) was added and then 98 percent potassium tert-butoxide (101.9 g) was added between 40 °C to 55 °C.(xv) This mixture was stirred for 15 min.(xvi) Toluene and NMP were added to Mixture A.(xvii) This mixture was heated up to 90 °C to 95 °C.(xviii) This mixture was stirred for 4 h then cooled down to ambient temperature.(xix) Water (325.5 ml) was added and a phase cut (organic phase up) was conducted.(xx) Water (162.8 ml) was added and a phase cut (organic phase up) was conducted.(xxi) Water (325.5 ml) was added and a phase cut (organic phase up) was conducted.(xxii) Solvent was distilled out and ethanol (1672 ml) was added.(xxiii) This mixture was loaded into a Parr reactor.(xxiv) This mixture was flushed with nitrogen.(xxv) 50 percent wet 10 percent Pd/C (3 g) was added.(xxiv) The mixture was then flushed with hydrogen.(xxv) The mixture was heated at 50 °C and pressurized up to 50 psi.(xxvi) The mixture was stirred for 5 h.(xxvii) The mixture was cooled down to ambient temperature.(xxviii) The Parr reactor was depressurized down to atmospheric pressure and hydrogen was released from the mixture.(xxix) The mixture was filtered on a pad of Hyflo Super Cel.(R). (55.6 g).(xxx) The mixture was rinsed with ethanol (167.2 ml)(xxxi) Solvent was distilled from the mixture at atmospheric pressure.(xxxii) 4-fluoro-3-methoxyphenol was disti.led at 125 °C under 1 mbar.

Reference： [1]Patent: WO2012/27134,2012,A1 .Location in patent: Page/Page column 2; 3; 4

8
[ 117902-15-5 ]
[ 1185836-63-8 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 4935 - 4938

9
[ 1359030-02-6 ]
[ 117902-15-5 ]
[ 1359028-44-6 ]

Yield	Reaction Conditions	Operation in experiment
19 mg	With potassium carbonate; In acetone; at 65℃; for 12h;Inert atmosphere;	Example 172 3-(5-{5-[(4-Fluoro-3-methoxyphenoxy)methyl]-1-methyl-1H-pyrazol-4-yl}-1,2,4-oxadiazol-3-yl)benzenesulfonamide Under a nitrogen atmosphere, a mixture of the 3-{5-[5-(bromomethyl)-1-methyl-1H-pyrazol-4-yl]-1,2,4-oxadiazol-3-yl}benzenesulfonamide (100 mg) obtained in Production Example 39, <strong>[117902-15-5]4-fluoro-3-methoxyphenol</strong> (43 mg), potassium carbonate (42 mg) and acetone (1.2 mL) was stirred at 65° C. for 12 hours. Thereafter, the reaction solution was purified by column chromatography (NH silica gel cartridge, chloroform:methanol=98:2 to 90:10). The obtained solid was washed with chloroform, so as to obtain the title compound (19 mg) in the form of a colorless solid. 1H NMR (500 MHz, DMSO-d6) delta ppm 3.75 (s, 3H) 4.02 (s, 3H) 5.67 (s, 2H) 6.65-6.71 (m, 1H) 6.89-6.93 (m, 1H) 7.13-7.18 (m, 1H) 7.56 (br. s., 2H) 7.79 (t, J=7.8 Hz, 1H) 8.01-8.06 (m, 1H) 8.20-8.25 (m, 1H) 8.27 (s, 1H) 8.49-8.52 (m, 1H); MS (ESI neg.) m/z: 458 [M-H]-

Reference： [1]Patent: US2013/137865,2013,A1 .Location in patent: Paragraph 0898; 0899; 0900

10
[ 503855-49-0 ]
[ 117902-15-5 ]
[ 1393826-47-5 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 1825 - 1836

11
[ 1019767-70-4 ]
[ 117902-15-5 ]
[ 1393826-54-4 ]

Reference： [1]Medicinal Chemistry Research,2013,vol. 22,p. 1825 - 1836

12
[ 128495-46-5 ]
[ 117902-15-5 ]

Yield	Reaction Conditions	Operation in experiment
35%		Intermediate 104-fluoro-3-(methyloxy)phenolTo a solution of 4-fluoro-3-(methyloxy)benzaldehide (1.54 g, 10 mmol) in DCM (30 mL) metachloroperbenzoic acid (2.59 g, 15 mmol) was added portionwise and the reaction mixture was stirred for 3 hours at room temperature. A second portion of m-CPBA (2.59 g, 15 mmol) wasadded and the reaction mixture was stirred for further 18 hrs. The mixture was diluted with DCM (100 mL), washed with an aqueous saturated solution of Na25203 (2x100 mL) and then with an aqueous saturated solution of NaHCO3(50 mL), dried over Na2SO4 and concentrated in vacuo to yield a yellow gum, which was re-dissolved in MeOH (20 mL) and Triethylamine (0.1 ml) was added. The reaction mixture was stirred for 18 hrs at room temperature and concentrated in vacuo. The residue was re-dissolved in Et20 (100 mL) and extracted with an aqueous iN solution of NaOH (50 mL). The aqueous layer was acidified with aqueous 2N HCIto pH=1 and extracted with Et20 (2x50 mL). The combined organic layers were dried overNa2SO4 and concentrated in vacuo to afford the title compound (830 mg, yield: 35percent).1HNMR (400 MHz, CDCI3): 6 ppm 6.81-6.85 (1H, t), 6.40-6.43 (1H, m), 6.21-6.24 (1H, m), 4.61(1H, s), 3.76 (3H, s).

Reference： [1]Patent: WO2013/175215,2013,A1 .Location in patent: Page/Page column 70 ; 71

13
[ 854778-31-7 ]
[ 117902-15-5 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3522 - 3533

14
[ 407640-40-8 ]
[ 117902-15-5 ]
1-(5-fluoro-2-hydroxy-4-methoxyphenyl)-2-(4-fluoro-2-methylphenyl)ethanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3522 - 3533

15
[ 117902-15-5 ]
C₁₇H₁₂F₂O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3522 - 3533

16
[ 117902-15-5 ]
C₁₇H₁₁BrF₂O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3522 - 3533

17
[ 117902-15-5 ]
C₁₆H₉BrF₂O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3522 - 3533

18
[ 117902-15-5 ]
C₂₂H₂₃BrF₂O₄Si [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3522 - 3533

19
[ 117902-15-5 ]
C₃₅H₃₈F₂O₇Si [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3522 - 3533

20
[ 117902-15-5 ]
(E)-3-(4-(6-fluoro-3-(4-fluoro-2-methylphenyl)-7-hydroxy-2-oxo-2H-chromen-4-yloxy)phenyl)acrylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3522 - 3533

21
[ 117902-15-5 ]
C₁₂H₁₅FO₄ [ No CAS ]

Reference： [1]Patent: WO2016/149393,2016,A1

22
[ 117902-15-5 ]
C₁₂H₁₄BrFO₄ [ No CAS ]

Reference： [1]Patent: WO2016/149393,2016,A1

23
[ 117902-15-5 ]
C₁₇H₂₂BrFO₆ [ No CAS ]

Reference： [1]Patent: WO2016/149393,2016,A1

24
[ 117902-15-5 ]
C₂₈H₄₀BFO₈ [ No CAS ]

Reference： [1]Patent: WO2016/149393,2016,A1

25
[ 117902-15-5 ]
C₂₉H₄₂BFO₈ [ No CAS ]

Reference： [1]Patent: WO2016/149393,2016,A1

26
[ 117902-15-5 ]
6-fluoro-2-hydroxy-7-methoxy-3,4-dihydro-1,2-benzoxaborinine-8-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2016/149393,2016,A1

27
[ 24424-99-5 ]
[ 117902-15-5 ]
C₁₂H₁₅FO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With dmap; In tetrahydrofuran; at 20℃; for 2h;	To a solution of 34A (500 mg, 3.52 mmol, 1.0 eq) in THF (5 mL) was added Boc20 (921 mg, 4.23 mmol, 1.2 eq) and DMAP (22 mg, 0.17 mmol, 0.05 eq). The mixture was stirred at room temperature for 2 hours before it was concentrated in vacuo. (0883) The residue was purified by column chromatography (PE EA = 20: 1 to 5: 1) to give 34B (0884) (767 mg, 90percent).

Reference： [1]Patent: WO2016/149393,2016,A1 .Location in patent: Paragraph 0333

28
(1s,3s)-3-methoxycyclobutanol [ No CAS ]
[ 117902-15-5 ]
1-fluoro-2-methoxy-4-((1r,3r)-3-methoxycyclobutoxy)benzene [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 96 - 101

29
[ 117902-15-5 ]
2-(2-fluoro-3-methoxy-5-((1r,3r)-3-methoxycyclobutoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 96 - 101

30
[ 117902-15-5 ]
C₂₅H₂₉FO₆ [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 96 - 101

31
[ 117902-15-5 ]
C₂₆H₂₉FO₆ [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 96 - 101

32
[ 454-16-0 ]
[ 117902-15-5 ]

Reference： [1]Patent: WO2017/132928,2017,A1

33
[ 64465-53-8 ]
[ 117902-15-5 ]

Yield	Reaction Conditions	Operation in experiment
46.7%	With sulfuric acid; sodium nitrite; at 0 - 100℃; for 0.5h;	To a suspension of compound 202 (4.0 g, 28.0 mmol) in 30 percent sulfuric acid (15mL) was added sodium nitrite (2.15 g, 31.0 mmol) at 0 °C. The reaction was stirred at 0 °Cfor 20 minutes, and then was added to 60percent sulfuric acid (15 mL) at 100 °C and stirred for 30mm. The reaction mixture was neutralized with anhydrous NaHCO3 and extracted with ethylacetate. The organic layer was washed with water and brine, dried over anhydrous sodiumsulfate and evaporated in vacuo. The crude product was purified by column chromatography(hexanes/dichloromethane: 3/1) to afford the title compound 203 (1.84 g, 46.7 percent yield) as acolorless oil. ?HNIVIR(400 1VIHz, DMSO-d6): 3.76 (s, 3H), 6.24-6.27 (m, 1H), 6.51 (dd, J 6.8, 2.8 Hz, 1H), 6.96 (dd, J 11.2, 8.4 Hz, 1H), 9.36 (s, 1H).

Reference： [1]Patent: WO2017/132928,2017,A1 .Location in patent: Paragraph 000102

34
[ 117902-15-5 ]
1-(3-fluoro-2-methoxy-6-(methoxymethoxy)phenyl)ethanol [ No CAS ]

Reference： [1]Patent: WO2017/132928,2017,A1

35
[ 117902-15-5 ]
1-(3-fluoro-2-methoxy-6-(methoxymethoxy)phenyl)ethanone [ No CAS ]

Reference： [1]Patent: WO2017/132928,2017,A1

36
[ 107-30-2 ]
[ 117902-15-5 ]
1-fluoro-2-methoxy-4-(methoxymethoxy)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%		To a mixture of compound 203 (4.8 g, 33.8 mmol) in DMF was added sodium hydride (2.7 g, 67.6 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 2 hours. Chloro(methoxy)methane (4.1 g, 50.7 mmol) was then added in ice bath. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (hexanes/ethyl acetate: 10/1) to afford the title compound 204 (4. 5 g, 86 percent yield) as a colorless oil. ?H NIVIR (400 1VIHz, DMSO-d6):3.38 (s, 3H), 3.81 (s, 3H), 5.16 (m, 2H), 6.54-6.56 (m, 1H), 6.80 (dd, J 7.6, 2.0 Hz, 1H), 6.80 (dd,J 11.6, 9.2Hz, 1H).

Reference： [1]Patent: WO2017/132928,2017,A1 .Location in patent: Paragraph 000103

37
[ 117902-15-5 ]
2-iodo-4-fluoro-5-methoxyphenol [ No CAS ]

Reference： [1]MedChemComm,2018,vol. 9,p. 316 - 327

38
[ 117902-15-5 ]
2-iodo-4-fluoro-5-methoxyphenyl acetate [ No CAS ]

Reference： [1]MedChemComm,2018,vol. 9,p. 316 - 327

39
[ 117902-15-5 ]
2-((4-methoxyphenyl)ethynyl)-4-fluoro-5-methoxyphenyl acetate [ No CAS ]

Reference： [1]MedChemComm,2018,vol. 9,p. 316 - 327

40
[ 117902-15-5 ]
5-fluoro-6-methoxy-2-phenylbenzofuran-3-carbaldehyde [ No CAS ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 4935 - 4938

41
[ 626-05-1 ]
[ 117902-15-5 ]
2-bromo-6-(4-fluoro-3-methoxyphenoxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With sodium hydride; In N,N-dimethyl-formamide; at 100℃;	A mixture of sodium hydride (60percent w/w) (88 mg, 2.2 mmol, 1.1 eq) in anhydrous dimethylformamide (5.0 mL) was cooled down to 0 °C and 4?fluoro-3-methoxyphenol (2d) (184 mg, 2.0 mmol, 1.0 eq) was slowly added under argon. After 5 min a solution of 2,6-dibromopyridine (2c) (474 mg, 2.0 mmol, 1.0 eq) in anhydrous dimethylformamide (5.0 mL) was slowly added at room temperature and the reaction mixture was stirred overnight at 100 °C. The mixture was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. The crude product was purified by column chromatography (cyclohexane/ethyl acetate 19:1) to give 154 mg (0.52 mmol, 26percent) of the analytically pure compound. C12H9BrFNO2; MW 298; 1H NMR (CDCl3, 400 MHz): delta 7.52 (t, J = 7.9 Hz, 1H), 7.20 (d, J = 7.6 Hz, 1H), 7.07 (dd, J = 10.9 Hz, 8.8 Hz, 1H), 6.79 (dd, J = 7.4 Hz, 2.6 Hz, 1H), 6.77 (d, J = 8.1 Hz, 1H), 6.66 (ddd, J = 8.8 Hz, 3.6 Hz, 2.8 Hz, 1H), 3.86 (s, 3H); 13C NMR (CDCl3, 100 MHz): delta 163.0 (d, J = 1.3 Hz), 149.8 (d, J = 241.3 Hz), 149.7 (d, J = 3.2 Hz), 148.4 (d, J = 12.1 Hz), 141.4, 139.3, 122.6, 116.3 (d, J = 20.0 Hz), 112.8 (d, J = 7.0 Hz), 109.5, 107.2 (d, J = 2.3 Hz), 56.4; MS (ESI): 298, 300 (M+H)+.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 155,p. 61 - 76

42
[ 117902-15-5 ]
2-(4-fluoro-3-methoxyphenoxy)-6-(2-fluoro-3-methoxyphenyl)pyridine [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 155,p. 61 - 76

43
[ 117902-15-5 ]
2-fluoro-3-[6-(4-fluoro-3-hydroxyphenoxy)pyridin-2-yl]phenol [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 155,p. 61 - 76

44
[ 872-85-5 ]
[ 122536-76-9 ]
[ 117902-15-5 ]
tert-butyl ((3R)-1-((5-fluoro-2-hydroxy-4-methoxyphenyl)(pyridin-4-yl)methyl)pyrrolidine-3-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41.5%	In ethanol; hexane; at 20℃;	General procedure: A solution of Sesamol (17a, 138 mg, 1 mmol), 4-pyridinecarboxaldehyde (18a, 107 mg, 1 mmol) and pyrrolidine(16a, 71 mg, 1 mmol) in 1 mL 1:1 ethanol/n-hexane was stirred atroom temperature overnight. After the reaction was completedmonitored by TLC, the solution was concentrated. The residue waspurified by Isolera Biotage LPLC (PE/EA 1:1) to give 9 (247 mg,82.9%) as a foam solid.

Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 223

45
[ 3934-20-1 ]
[ 117902-15-5 ]
2-chloro-4-(4-fluoro-3-methoxyphenoxy)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With sodium hydrogencarbonate; In tetrahydrofuran; ethanol; at 20℃; for 6h;	To a stirred solution of 2,4-dichloropyrimidine (500 mg, 3.36 mmol), 4-fluoro-3- methoxyphenol (382 mg, 2.69 mmol) in tetrahydrofuran (2 mL), ethanol (4mL), was added sodium hydrogen carbonate (713 mg, 8.39 mmol) and stirred for 6 h at room temperature. The progress of reaction mixture was monitored by TLC and LCMS. After completion, the reaction mixture was quenched by water and extracted with ethyl acetate, and the organic layer was dried under reduced pressure. The resulting crude was purified by column chromatography using ethyl acetate -hexane (product elutes at 20% ethyl acetate). Purification resulted in pure 2-chloro-4-(4-fluoro-3- methoxyphenoxy) pyrimidine as white solid (350 mg, 41%). LCMS (ES) m/z calcd. for Cl 1H8C1FN202, 254.3; found, 255.19 [M + H]

Reference： [1]Patent: WO2021/211974,2021,A1 .Location in patent: Paragraph 00189-00190

46
[ 32710-65-9 ]
[ 117902-15-5 ]
2-chloro-6-(4-fluoro-3-methoxyphenoxy)pyridine-4-carbonitrile [ No CAS ]