[ CAS No. 17100-64-0 ] {[proInfo.proName]}

Name: 17100-64-0|(4-Bromo-3-methoxyphenyl)methanol|98%
Brand: Ambeed
SKU: A145462
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Quality Control of [ 17100-64-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 17100-64-0 ]

Product Details of [ 17100-64-0 ]

CAS No. :	17100-64-0	MDL No. :	MFCD11053671
Formula :	C₈H₉BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KXUYHKRDJBTPDF-UHFFFAOYSA-N
M.W :	217.06	Pubchem ID :	13551345
Synonyms :

Calculated chemistry of [ 17100-64-0 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.76
TPSA :	29.46 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) :	-6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.22
Log Po/w (XLOGP3) :	1.03
Log Po/w (WLOGP) :	1.8
Log Po/w (MLOGP) :	1.95
Log Po/w (SILICOS-IT) :	2.34
Consensus Log Po/w :	1.87

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.11
Solubility :	1.7 mg/ml ; 0.00783 mol/l
Class :	Soluble
Log S (Ali) :	-1.24
Solubility :	12.5 mg/ml ; 0.0577 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.21
Solubility :	0.133 mg/ml ; 0.000611 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.4

Safety of [ 17100-64-0 ]

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 [ 17100-64-0 ]

* 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 [ 17100-64-0 ]
Downstream synthetic route of [ 17100-64-0 ]

[ 17100-64-0 ] Synthesis Path-Upstream 1~7

1
[ 6971-51-3 ]
[ 17100-64-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 8 h;	To a solution of 3-methoxybenzyl alcohol (20.0 g, 145 mmol) in THF (400 mL) was added N-bromosuccinimide (26 g, 146 mmol) and the resultant mixture was stirred at room temperature for 8 h. Ether (500 mL) was added and the mixture was washed with water (3×100 mL). The solution was dried over magnesium sulfate and concentrated to afford the title compound (31.2 g, 99percent) which was used as such for the next step.
88%	With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 1.5 h;	The compound 3-methoxybenzyl alcohol (10 g, 72.4 mmol) was dissolved in a mixture of acetonitrile (250 mL) and water (250 mL) and then sodium bromate (19.1 g, 127 mmol) and sodium bisulfite (13.2 g, 127 mmol) were added. The reaction solution was stirred at room temperature for 1.5 hours, quenched with a saturated aqueous solution of sodium thiosulfate (250 mL) and then extracted with dichloromethane (200 mL3). The combined organic phase was washed with water (200 mL3) and brine (20 mL) sequentially, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, the residue was purified by silica gel TLC preparative plate (petroleum ether: ethyl acetate=3:1) to give 9-e as a yellow solid (1.39 g, yield 88percent). ¹H-NMR (400 MHz, MeOD) δ: 7.41 (d, J=12 Hz, 1H), 7.06 (d, J=4 Hz, 1H), 6.71 (dd, J=4 Hz, J=8 Hz, 1H), 4.70 (d, J=8 Hz, 2H), 3.81 (s, 3H) ppm
86%	With sodium hydrogensulfite; potassium bromide In water; acetonitrile at 20℃; for 1.5 h;	Method 10E: using the appropriate benzyl alcohol.Aromatic Bromination of the Benzyl AlcoholThe benzyl alcohol was dissolved in an equivolumetric acetonitrile/water mixture. Potassium bromide, then sodium hydrogenosulfite were added and the reaction mixture was stirred at room temperature for 1 h30. A sodium bisulfate 10percent solution was a added and the mixture was extracted with diethyl ether. The organic layer was washed with a saturated sodium carbonate solution, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The product was chromatographed over silica gel.10.8.1 (4-bromo-3-methoxyphenyl)methanol Prepared following the aromatic bromination method previously described (Method 10E) using (3-methoxyphenyl)methanol. The product was chromatographed over silica gel (eluent petroleum ether/ethyl acetate 95/5). The product was obtained as a beige solid. Yield: 86percent Rf (petroleum ether/ethyl acetate 90/10): 0.57 NMR ¹H (CDCl₃): 3.66 (s, 1H); 3.73 (s, 3H); 4.61 (s, 2H); 6.64 (dd, 1H, J=7.5 Hz, J=2.5 Hz); 7.01 (d, 1H, J=2.5 Hz); 7.34 (d, 1H, J=7.5 Hz).

Reference： [1] Patent: US9725406, 2017, B1, . Location in patent: Page/Page column 7-8
[2] Tetrahedron, 2005, vol. 61, # 49, p. 11692 - 11696
[3] Patent: US2018/208604, 2018, A1, . Location in patent: Paragraph 0201-0203
[4] Patent: US2010/4159, 2010, A1, . Location in patent: Page/Page column 59; 64
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1010 - 1014
[6] Synthetic Communications, 2007, vol. 37, # 9, p. 1571 - 1577

2
[ 17100-63-9 ]
[ 17100-64-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With lithium aluminium tetrahydride In tetrahydrofuran at -40℃; for 2 h; Inert atmosphere	To a mixture of methyl 4-bromo-3-methoxy-benzoate (3.00 g, 12.24 mmol) in THF (40) was added LiAlH₄ (1.39 g, 36.72 mmol) at -40°C under N₂, then the mixture was stirred at -40°C for 2 hours. To the mixture was added 0 (1.76 g) dropwise at -40 °C, then the mixture was stirred at 0 °C for 0.5 hour and 50 °C for 0.5 hour, filtered through Celite, and eluted by THF (100 mL x 2). The filtrate was concentrated. The residue was dissolved in EtOAc (200 mL), washed with water (30 mL x 2) and brine (50 mL), dried over Na₂S0₄, filtered and concentrated to afford the crude product of compound 17-2 (2.50 g, 11.52 mmol, 94percent yield) as an oil, *H NMR (400MHz, DMSO-d₆) δ_Η = 7.49 (d, 1H), 7.06 (s, 1H), 6.84 (d, 1H), 5.29 (t, 1H), 4.47 (d, 2H), 3.83 (s, 3H).
2.5 g	Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at -40℃; for 2 h; Stage #2: With water In tetrahydrofuran at -40 - 50℃; for 1 h;	To a mixture of A-26 (3.00 g, 12.24 mmol) in THF (40 mL) was added LiAlH4 (1.39 g, 36.72 mmol) at -40C under N2, and the mixture was stirred at -40C for 2 hours. To the mixture was added _0 (1.76 g) dropwise at -40 C, and the mixture was stirred at 0 C for 0.5 hour, followed by stirring at 50 C for 0.5 hour. The mixture was then filtered through Celite, eluted by THF (100 mL x 2), concentrated, dissolved in EtOAc (200 mL), washed with water (30 mL x 2) and brine (50 mL), dried over Na2S04, filtered and concentrated to give A-27 (2.50 g, 11.52 mmol) as an oil. 1H NMR (400MHz DMSO-d6) _ = 7.49 (d, 1H), 7.06 (s, 1H), 6.84 (d, 1H), 5.29 (t, 1H), 4.47 (d, 2H), 3.83 (s, 3H).

Reference： [1] Patent: WO2018/98491, 2018, A1, . Location in patent: Page/Page column 96
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2382 - 2391
[3] CrystEngComm, 2017, vol. 19, # 4, p. 603 - 607
[4] Patent: WO2018/98499, 2018, A1, . Location in patent: Page/Page column 137

3
[ 56256-14-5 ]
[ 17100-64-0 ]

Reference： [1] Patent: US4707483, 1987, A,
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 819 - 823

4
[ 6971-51-3 ]
[ 17100-64-0 ]
[ 199436-55-0 ]

Reference： [1] Australian Journal of Chemistry, 1997, vol. 50, # 8, p. 831 - 840

5
[ 99-06-9 ]
[ 17100-64-0 ]

Reference： [1] Chemical Communications, 2014, vol. 50, # 100, p. 15905 - 15908

6
[ 14348-38-0 ]
[ 77-78-1 ]
[ 17100-64-0 ]

Reference： [1] Chemical Communications, 2014, vol. 50, # 100, p. 15905 - 15908

7
[ 17100-64-0 ]
[ 43192-34-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1010 - 1014

[ 17100-64-0 ] Synthesis Path-Downstream 1~71

1
[ 17100-64-0 ]
[ 137432-38-3 ]

Reference： [1]Journal of the American Chemical Society,1991,vol. 113,p. 8909 - 8916
[2]Chemical Communications,2014,vol. 50,p. 15905 - 15908
[3]CrystEngComm,2017,vol. 19,p. 603 - 607

2
[ 6971-51-3 ]
[ 17100-64-0 ]
[ 199436-55-0 ]

Reference： [1]Australian Journal of Chemistry,1997,vol. 50,p. 831 - 840

4
[ 110-87-2 ]
[ 17100-64-0 ]
[ 17100-70-8 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 11692 - 11696
[2]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 2382 - 2391

5
[ 6971-51-3 ]
[ 17100-64-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With N-Bromosuccinimide; In tetrahydrofuran; at 20℃; for 8h;	To a solution of 3-methoxybenzyl alcohol (20.0 g, 145 mmol) in THF (400 mL) was added N-bromosuccinimide (26 g, 146 mmol) and the resultant mixture was stirred at room temperature for 8 h. Ether (500 mL) was added and the mixture was washed with water (3×100 mL). The solution was dried over magnesium sulfate and concentrated to afford the title compound (31.2 g, 99percent) which was used as such for the next step.
88%	With sodium bromate; sodium hydrogensulfite; In water; acetonitrile; at 20℃; for 1.5h;	The compound 3-methoxybenzyl alcohol (10 g, 72.4 mmol) was dissolved in a mixture of acetonitrile (250 mL) and water (250 mL) and then sodium bromate (19.1 g, 127 mmol) and sodium bisulfite (13.2 g, 127 mmol) were added. The reaction solution was stirred at room temperature for 1.5 hours, quenched with a saturated aqueous solution of sodium thiosulfate (250 mL) and then extracted with dichloromethane (200 mL3). The combined organic phase was washed with water (200 mL3) and brine (20 mL) sequentially, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, the residue was purified by silica gel TLC preparative plate (petroleum ether: ethyl acetate=3:1) to give 9-e as a yellow solid (1.39 g, yield 88percent). 1H-NMR (400 MHz, MeOD) delta: 7.41 (d, J=12 Hz, 1H), 7.06 (d, J=4 Hz, 1H), 6.71 (dd, J=4 Hz, J=8 Hz, 1H), 4.70 (d, J=8 Hz, 2H), 3.81 (s, 3H) ppm
86%	With sodium hydrogensulfite; potassium bromide; In water; acetonitrile; at 20℃; for 1.5h;	Method 10E: using the appropriate benzyl alcohol.Aromatic Bromination of the Benzyl AlcoholThe benzyl alcohol was dissolved in an equivolumetric acetonitrile/water mixture. Potassium bromide, then sodium hydrogenosulfite were added and the reaction mixture was stirred at room temperature for 1 h30. A sodium bisulfate 10percent solution was a added and the mixture was extracted with diethyl ether. The organic layer was washed with a saturated sodium carbonate solution, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The product was chromatographed over silica gel.10.8.1 (4-bromo-3-methoxyphenyl)methanol Prepared following the aromatic bromination method previously described (Method 10E) using (3-methoxyphenyl)methanol. The product was chromatographed over silica gel (eluent petroleum ether/ethyl acetate 95/5). The product was obtained as a beige solid. Yield: 86percent Rf (petroleum ether/ethyl acetate 90/10): 0.57 NMR 1H (CDCl3): 3.66 (s, 1H); 3.73 (s, 3H); 4.61 (s, 2H); 6.64 (dd, 1H, J=7.5 Hz, J=2.5 Hz); 7.01 (d, 1H, J=2.5 Hz); 7.34 (d, 1H, J=7.5 Hz).

Reference： [1]Patent: US9725406,2017,B1 .Location in patent: Page/Page column 7-8
[2]Tetrahedron,2005,vol. 61,p. 11692 - 11696
[3]Patent: US2018/208604,2018,A1 .Location in patent: Paragraph 0201-0203
[4]Patent: US2010/4159,2010,A1 .Location in patent: Page/Page column 59; 64
[5]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1010 - 1014
[6]Synthetic Communications,2007,vol. 37,p. 1571 - 1577

6
[ 17100-64-0 ]
[ 872516-87-5 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 11692 - 11696
[2]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 2382 - 2391

7
[ 56256-14-5 ]
[ 17100-64-0 ]

Yield	Reaction Conditions	Operation in experiment
	With borane; In tetrahydrofuran; methanol;	EXAMPLE 12 4-Bromo-3-methoxybenzoic acid (23.1 g, 0.1 m) dissolved in tetrahydrofuran (200 ml) is added to 1M borane in tetrahydrofuran (150 ml) stirred at 5°. The mixture is refluxed, cooled, treated with methanol, refluxed and concentrated in vacuo to give 4-bromo-3-methoxybenzyl alcohol.

Reference： [1]Patent: US4707483,1987,A
[2]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 819 - 823

8
[ 17100-64-0 ]
[ 113081-49-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With thionyl chloride;	A mixture of 17-2 (2.50 g, 11.52 mmol) in SOCl2 (15 mL) was stirred at 70 °C for 2 hours. After cooling to r.t, the mixture was concentrated, and the residue was diluted with EtOAc (150 mL). The organic phase was washed with water (30 mL) and brine (30 mL), dried over Na2S04, filtered and concentrated to afford compound 17-3 (2.60 g, 11.04 mmol, 96percent yield) as an oil. 1H NMR (400MHz, DMSO-d6) deltaEta = 7.57 (d, 1H), 7.20 (d, 1H), 6.97 (dd, 1H), 4.74 (s, 2H), 3.86 (s, 3H).
	With pyridine; thionyl chloride; In toluene;	4-Bromo-3-methoxybenzyl alcohol (21.7 g, 0.1 m) dissolved in toluene (200 ml) containing pyridine (11.8 g, 0.15 m) is stirred at 5° and treated wiih thionyl chloride (23.8 g, 0.2 m). The mixture is stirred, diluted with water and the organic layer washed with dilute hydrochloric acid, dried and concentrated in vacuo to give 4-bromo-3-methoxybenzyl chloride.
	With pyridine; thionyl chloride; In toluene;	4-Bromo-3-methoxybenzyl alcohol (2l.7 g, 0.l m) dissolved in toluene (200 ml) containing pyridine (ll.8 g, 0.l5 m) is stirred at 5° and treated with thionyl chloride (23.8 g, 0.2 m). The mixture is stirred, diluted with water and the organic layer washed with dilute hydrochloric acid, dried and concentrated in vacuo to give 4-bromo-3-methoxybenzyl chloride.

	With thionyl chloride; In N,N-dimethyl-formamide; at 0 - 20℃; for 24.33h;	To a solution of <strong>[17100-64-0]4-bromo-3-methoxybenzyl alcohol</strong> (31.0 g, 143 mmol) in DMF (200 mL) at 0° C. was added thionyl chloride (17.5 mL, 241 mmol) dropwise over the course of 20 minutes. The resultant mixture was allowed to warm to room temperature and stirring was continued for 24 hours. The reaction was quenched with water and extracted with ether. The combined organic extracts were washed with water and dried over magnesium sulfate before being concentrated in vacuo. The residue was taken up in triethylphosphite (200 mL) and the solution was heated to 150° C. for 4 hours. Excess triethylphosphite was removed in vacuo to afford the crude product which was purified by vacuum distillation to afford the title compound as a colorless oil which solidified upon standing (34.7 g, 72percent).
	With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 12h;	Into a 100-mL 3-necked round-bottom flask was placed (4-bromo-3- methoxyphenyl)methanol (1 g, 4.61 mmol, 1.00 equiv), dichloromethane (30 mL), thionyl chloride (1.64 g, 13.90 mmol, 3.00 equiv), and N,N-dimethylformamide (0.2 mL). The resulting solution was stirred for 12 h at 20 °C. The resulting mixture was washed with 3x10 mL of H20. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 1 g (92percent) of the title compound as a red crude oil. Analytical Data: ?H NMR (300 MHz, DMSO-d6) 7.57 (d, J 8.1 Hz, 1H), 7.20 (d, J 2.0 Hz, 1H), 6.97 (d, J= 8.1, 2.0 Hz, 1H), 4.74 (s, 2H), 3.85 (s, 3H).
2.6 g	With thionyl chloride; at 70℃; for 2h;	A mixture of A-27 (2.50 g, 11.52 mmol) in SOCl2 (15 mL) was stirred at 70 C for 2 hours. The mixture was concentrated, and the residue was diluted with EtOAc (150 mL). The organic phase was washed with water (30 mL) and brine (30 mL), dried over Na2S04, filtered and concentrated to give A-28 (2.60 g, 11.04 mmol) as an oil. H NMR (400MHz DMSO-ifc) _ = 7.57 (d, 1H), 7.20 (d, 1H), 6.97 (dd, 1H), 4.74 (s, 2H), 3.86 (s, 3H).

Reference： [1]Patent: WO2018/98491,2018,A1 .Location in patent: Page/Page column 96-97
[2]Patent: US4707483,1987,A
[3]Patent: EP244088,1989,A3
[4]Patent: US9725406,2017,B1 .Location in patent: Page/Page column 7; 8
[5]Patent: WO2018/64557,2018,A1 .Location in patent: Paragraph 0608; 0609; 0610; 0611
[6]Patent: WO2018/98499,2018,A1 .Location in patent: Page/Page column 137

9
[ 17100-64-0 ]
[ 1148110-16-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 819 - 823

10
[ 17100-64-0 ]
C₂₁H₁₈Br₂O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1010 - 1014

11
[ 17100-64-0 ]
[ 43192-34-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1010 - 1014

12
[ 37860-51-8 ]
[ 17100-64-0 ]
[ 1355460-61-5 ]

Yield	Reaction Conditions	Operation in experiment
74%		A suspension of NaH (1.8 g, 60percent in paraffin, 45 mmol) in THF (50 mL) was cooled to 0 °C. Addition of a cooled solution of 41 (3.66 g, 17 mmol) in THF (30 mL) was followed by stirring for 15 min. After adding tetraethylene glycol di-p-tosylate (1.12 mL, 2.8 mmol) the mixture was warmed to room temperature and stirred for 4 h. Addition of water was followed by extraction with EtOAc, drying (Na2SO4) and evaporation of the solvent. The residue was purified by flash-chromatography (hexane/EtOAc 6:1 to 1:1) to give 47 in 74percent yield (1.24 mg). EI-MS: m/z 592 (M+); 1H NMR: (CDCl3, 360 MHz) delta (ppm): 3.67-3.69 (m, 8H), 3.70-3.73 (m, 8H), 3.79 (s, 6H), 4.58 (s, 4H), 6.69 (dd, J1 = 8.5 Hz, J2 = 3.0 Hz, 1H), 7.08 (d, J = 3.0 Hz, 1H), 7.38 (d, J = 9.0 Hz, 1H). 13C NMR: (CDCl3, 150 MHz) delta (ppm): 55.5, 70.2, 70.6, 70.7, 70.8, 72.3, 112.6, 114.3, 114.7, 133.0, 138.7, 159.1; IR: (NaCl) nu (cm-1): 2868, 1595, 1469, 1354, 1296, 1111, 876, 810, 754.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 455 - 466

13
[ 592-55-2 ]
[ 17100-64-0 ]
[ 1355460-56-8 ]

Yield	Reaction Conditions	Operation in experiment
36%	With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 0 - 70℃;	General procedure: To a solution of 9 (62 mg, 0.3 mmol) and 2-bromoethyl ethyl ether (0.2 mL, 1.8 mmol) in dry THF (2.5 mL) was added dropwise KHMDS (1.8 mL, 0.5 M in toluene, 0.9 mmol) at 0 °C. After being stirred at ambient temperature for 2 h, the mixture was heated to 70 °C over night. After being cooled to room temperature the mixture was treated with water and extracted with CH2Cl2. The combined organic layers were washed with brine and dried over Na2SO4. After evaporation the crude product was purified by flash chromatography (hexane/EtOAc 3:2) to give 11a in 18percent yield (15 mg).

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 455 - 466

14
[ 17100-64-0 ]
[ 1355460-57-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 455 - 466

15
[ 17100-64-0 ]
[ 1355460-58-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 455 - 466

16
[ 17100-64-0 ]
[ 1355460-59-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 455 - 466

17
[ 17100-64-0 ]
[ 1355460-60-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 455 - 466

18
[ 17100-64-0 ]
[ 1355460-64-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 455 - 466

19
[ 17100-64-0 ]
[ 1355460-62-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 455 - 466

20
[ 17100-63-9 ]
[ 17100-64-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With lithium aluminium tetrahydride; In tetrahydrofuran; at -40℃; for 2h;Inert atmosphere;	To a mixture of methyl 4-bromo-3-methoxy-benzoate (3.00 g, 12.24 mmol) in THF (40) was added LiAlH4 (1.39 g, 36.72 mmol) at -40°C under N2, then the mixture was stirred at -40°C for 2 hours. To the mixture was added 0 (1.76 g) dropwise at -40 °C, then the mixture was stirred at 0 °C for 0.5 hour and 50 °C for 0.5 hour, filtered through Celite, and eluted by THF (100 mL x 2). The filtrate was concentrated. The residue was dissolved in EtOAc (200 mL), washed with water (30 mL x 2) and brine (50 mL), dried over Na2S04, filtered and concentrated to afford the crude product of compound 17-2 (2.50 g, 11.52 mmol, 94percent yield) as an oil, *H NMR (400MHz, DMSO-d6) deltaEta = 7.49 (d, 1H), 7.06 (s, 1H), 6.84 (d, 1H), 5.29 (t, 1H), 4.47 (d, 2H), 3.83 (s, 3H).
2.5 g		To a mixture of A-26 (3.00 g, 12.24 mmol) in THF (40 mL) was added LiAlH4 (1.39 g, 36.72 mmol) at -40C under N2, and the mixture was stirred at -40C for 2 hours. To the mixture was added _0 (1.76 g) dropwise at -40 C, and the mixture was stirred at 0 C for 0.5 hour, followed by stirring at 50 C for 0.5 hour. The mixture was then filtered through Celite, eluted by THF (100 mL x 2), concentrated, dissolved in EtOAc (200 mL), washed with water (30 mL x 2) and brine (50 mL), dried over Na2S04, filtered and concentrated to give A-27 (2.50 g, 11.52 mmol) as an oil. 1H NMR (400MHz DMSO-d6) _ = 7.49 (d, 1H), 7.06 (s, 1H), 6.84 (d, 1H), 5.29 (t, 1H), 4.47 (d, 2H), 3.83 (s, 3H).

Reference： [1]Patent: WO2018/98491,2018,A1 .Location in patent: Page/Page column 96
[2]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 2382 - 2391
[3]CrystEngComm,2017,vol. 19,p. 603 - 607
[4]Patent: WO2018/98499,2018,A1 .Location in patent: Page/Page column 137

21
[ 17100-64-0 ]
[ 1186304-32-4 ]