99873-30-0|4-Bromo-3-ethylphenol| Ambeed

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Quality Control of [ 99873-30-0 ] Purity: 95% SDS Specification

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Product Details of [ 99873-30-0 ]

CAS No. :	99873-30-0
Formula :	C₈H₉BrO
M.W :	201.06
SMILES Code :	OC1=CC=C(Br)C(CC)=C1
MDL No. :	MFCD16997652
InChI Key :	CAMRWHABCOLYHJ-UHFFFAOYSA-N
Pubchem ID :	15007732

Safety of [ 99873-30-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 99873-30-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	45.94
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.03
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.8
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.72
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.88
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.81
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.85

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.86
Solubility	0.0278 mg/ml ; 0.000138 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.92
Solubility	0.0242 mg/ml ; 0.00012 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.47
Solubility	0.068 mg/ml ; 0.000338 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-4.83 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.18

Application In Synthesis of [ 99873-30-0 ]

* 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 [ 99873-30-0 ]
Downstream synthetic route of [ 99873-30-0 ]

[ 99873-30-0 ] Synthesis Path-Upstream 1~1

1
[ 620-17-7 ]
[ 99873-30-0 ]

Yield	Reaction Conditions	Operation in experiment
7.25 g	With N-Bromosuccinimide In chloroform at 0 - 20℃; for 2 h;	At 0°C cooling in ice, a mixture of 7.33g of 3-ethylphenol and 600mL of chloroform was added 10.7g of N-bromosuccinimide. After the temperature was raised to room temperature and stirred for 2 hours, The reaction solution was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 7.25g of 4-bromo-3-ethylphenol (Referred to as 45A).
7.25 g	With N-Bromosuccinimide In chloroform at 0 - 20℃; for 2 h; Cooling with ice	Reference Production Example 45 (0707) While stirring a mixture of 7.33 g of 3-ethylphenol and 600 mL of chloroform under ice cooling at 0° C., 10.7 g of N-bromosuccinimide was added. After raising the temperature to room temperature and stirring for 2 hours, the reaction solution was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 7.25 g of 4-bromo-3-ethylphenol (referred to as 45A). (0708) ¹H-NMR (CDCl₃) δ: 7.37 (1H, d, J=8.2 Hz), 6.90 (1H, d, J=2.1 Hz), 6.69 (1H, dd, J=8.2, 2.1 Hz), 5.48 (1H, s), 2.61 (2H, q, J=7.6 Hz), 1.24 (3H, t, J=7.6 Hz).

References: [1] Patent: WO2011/34828, 2011, A1, . Location in patent: Page/Page column 84.
[2] Patent: EP2177513, 2010, A1, . Location in patent: Page/Page column 28.
[3] Patent: CN105392779, 2016, A, . Location in patent: Paragraph 1351; 1352; 1353; 1354.
[4] Patent: US2016/159755, 2016, A1, . Location in patent: Paragraph 0707; 0708.

[ 99873-30-0 ] Synthesis Path-Downstream 1~35

Yield	Reaction Conditions	Operation in experiment
80%		Example 24(e) 3-1H-Benzoimidazol-2-yl-6-(2-ethyl-4-hydroxyphenyl)-1H-indazole Example 24 (e) was prepared in a similar manner to that described for Example 24(a), except that 4-bromo-3-ethyl-phenol, prepared in 80% yield according to the procedure described by Carreno et. al., Syn. Lett., 11, 1241-42 (1997) for the synthesis of 4-bromo-3-methyl-phenol, was used instead of 4-bromo-2-methoxy-5-methyl-phenol in step (vi). 1H NMR (300 MHz, DMSO-d6) delta 13.66 (s, 1H), 13.02 (s, 1H), 9.43 (s, 1H), 8.49 (d, 1H, J=8.4 Hz), 7.72 (d, 1H, J=6.9 Hz), 7.53 (d, 1H, J=6.9 Hz), 7.44 (s, 1H), 7.18-7.25 (m, 3H), 7.06 (d, 1H, J=8.1 Hz), 6.75 (d, 1H, J=2.1 Hz), 6.66 (dd, 1H, J=8.1, 2.1 Hz), 2.50 (q, 2H, J=7.5 Hz), 1.04 (t, 3H, J=7.5 Hz). MS (ES) [m+H]/z calc'd 355, found 355; [m-H]/z calc'd 353, found 353.

3
[ 620-17-7 ]
[ 99873-30-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-Bromosuccinimide; trifluorormethanesulfonic acid; In acetonitrile; at -30 - 20℃; for 12.0h;Inert atmosphere;	To a solution of 3-ethylphenol (22, 1.22 g, 10 mmol) in acetonitrile (CH3CN, 15mL) at 30 C were added sequentially with trifluoromethanesulfonic acid (TfOH,N-bromosuccinimide (NBS, 1.79 g, 10 mmol). The resultingreaction mixture was allowed to warm up to room temperature, and then stirred atroom temperature for 12 hours. The mixture was added sequentially with water (10mL) and diethyl ether (10 mL). The aqueous phase was extracted with diethyl ether (3x 20 mL). The combined organic phases were washed sequentially with saturatedaqueous sodium sulfite solution (Na2SO3, 20 mL) and brine (20 mL), dried overanhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure.The residue was purified by column chromatography (20% ethyl acetate in petroleumether) silica gel to afford 4-bromo-3-ethylphenol (23) as a white solid (1.89 g).Yield: 94%; m.p. = 51 53 C; 1H NMR (400 MHz, CDCl3): = 7.36 (d, J = 8.6Hz, 1H), 6.74 (d, J = 2.9 Hz, 1H), 6.56 (dd, J = 8.6, 3.0 Hz, 1H), 5.28 (s, 1H), 2.69 (q,J = 7.6 Hz, 2H), 1.20 (t, J = 7.5 Hz, 3H); 13C NMR (100 MHz, CDCl3): =154.7, 144.6, 133.3, 116.4, 114.8, 114.5, 29.3, 13.9; max = 3342, 2969,2932, 2873, 1577, 1468, 1439, 1285, 1236, 1161, 1058, 1027, 863, 807 cm-1. HRMS(ESI): m/z calcd for C8H9BrNaO [M+Na]+: 222.9729; found: 222.9737.
36%	With bromine; acetic acid;	Step 1 : 4-Bromo-3-ethylphenolTo a solution of 3-ethylphenol (3.0 g, 24.6 mmol) in acetic acid (20 ml) was added bromine (4 g, 22 mmol) in acetic acid (10 ml) dropwise over 5 minutes. The mixture was stirred at room temperature for 18 hours. The mixture was poured into water (100 ml) and was extracted with ethyl acetate (100 ml). The organic layer was washed with aqueous sodium bicarbonate and then water, dried over magnesium sulfate and filtered. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel using 100% heptane and then 9: 1 heptane: ethyl acetate to give the title compound as an oil (1.6 g, 36%).
	With tetra-N-butylammonium tribromide; In methanol; dichloromethane; at 20℃; for 1.0h;Inert atmosphere;	Example 13 4-bromo-3-ethylphenol Under argon atmosphere, to the mixture of 3-ethylphenol(11.2g), methylene chloride(30mL), and methanol(20mL), tetra-n-butylammonium tribromide (24.9g) was added and stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate and the organic layer was washed with a 1N hydrochloric acid, water and saturated brine solution and was dried by anhydrous magnesium sulphate. The title compound (11.2 g) having the following physical data was obtained by removing the solvent. TLC:Rf 0.49(n-hexane:ethyl acetate:acetic acid=1:4); 1H-NMR: (CDCl3) delta 1.22, 2.69, 4.92, 6.57, 6.74, 7.37.

7.25 g	With N-Bromosuccinimide; In chloroform; at 0 - 20℃; for 2.0h;	At 0C cooling in ice, a mixture of 7.33g of 3-ethylphenol and 600mL of chloroform was added 10.7g of N-bromosuccinimide. After the temperature was raised to room temperature and stirred for 2 hours, The reaction solution was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 7.25g of 4-bromo-3-ethylphenol (Referred to as 45A).
7.25 g	With N-Bromosuccinimide; In chloroform; at 0 - 20℃; for 2.0h;Cooling with ice;	Reference Production Example 45 (0707) While stirring a mixture of 7.33 g of 3-ethylphenol and 600 mL of chloroform under ice cooling at 0 C., 10.7 g of N-bromosuccinimide was added. After raising the temperature to room temperature and stirring for 2 hours, the reaction solution was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 7.25 g of 4-bromo-3-ethylphenol (referred to as 45A). (0708) 1H-NMR (CDCl3) delta: 7.37 (1H, d, J=8.2 Hz), 6.90 (1H, d, J=2.1 Hz), 6.69 (1H, dd, J=8.2, 2.1 Hz), 5.48 (1H, s), 2.61 (2H, q, J=7.6 Hz), 1.24 (3H, t, J=7.6 Hz).

References: [1]Natural Product Research,2019,vol. 33,p. 2911 - 2916.
[2]Patent: WO2011/34828,2011,A1 .Location in patent: Page/Page column 84.
[3]Patent: EP2177513,2010,A1 .Location in patent: Page/Page column 28.
[4]Patent: CN105392779,2016,A .Location in patent: Paragraph 1351; 1352; 1353; 1354.
[5]Patent: US2016/159755,2016,A1 .Location in patent: Paragraph 0707; 0708.

4
[ 502434-59-5 ]
[ 99873-30-0 ]
[ 1116624-31-7 ]

Yield	Reaction Conditions	Operation in experiment
	With cesium chloride; In N,N-dimethyl-formamide; at 70℃;Inert atmosphere;	Example 14 (2S)-2-(4-bromo-3-ethylphenoxy)methyl-4-methyl-3,4-dihydro-2H-1,4-benzoxazine Under an argon atmosphere, to the mixture of the compound synthesised in Example 13 (11.2 g), the compound synthesised in Example 7 (16.9 g), and N,N-dimethylformamide(50mL), cesium chloride(18.2 g) was added and stirred overnight at 70C. The reaction mixture was diluted with ethyl acetate and the organic layer was washed with a 1N hydrochloric acid, water and saturated brine solution, and was dried with anhydrous magnesium sulphate. The title compound (17.0 g) having the following physical data was obtained by purifying the residue obtained by removing the solvent with silica gel column chromatography (n-hexane:ethyl acetate=6:1). TLC:Rf 0.49(n-hexane:ethyl acetate:acetic acid=1:6); 1H-NMR: (CDCl3) delta 1.22, 2.69, 2.91, 3.23, 3.38, 4.09, 4.18, 4.61, 6.63, 6.82, 7.39.

References: [1]Patent: EP2177513,2010,A1 .Location in patent: Page/Page column 28-29.

5
[ 99873-30-0 ]
[ 183158-34-1 ]
[ 1279015-58-5 ]

Yield	Reaction Conditions	Operation in experiment
39%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 6.0h;Reflux;	Step 2: 2-Ethyl-2',3'-dimethyl-biphenyl-4-olA mixture of <strong>[99873-30-0]4-bromo-3-ethylphenol</strong> (1.6 g, 7.96 mmol), 2,3-dimethylphenylboronic acid (1.2 g, 7.96 mmol), tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.86 mmol) and a 2M sodium carbonate solution (6 ml) in 1 ,2-dimethoxyethane(70 ml) was heated at reflux for 6 hours. The mixture was cooled and was poured into an aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate (150 ml). The organic layer was washed with water, dried over magnesium sulfate and filtered. The concentrated filtrate was purified by flash chromatography on silica gel using 100% heptane, then 9: 1 heptane:ethyl acetate to provide the title compound (0.7 g, 39%).

References: [1]Patent: WO2011/34828,2011,A1 .Location in patent: Page/Page column 85.

6
[ 99873-30-0 ]
[ 1279014-72-0 ]

References: [1]Patent: WO2011/34828,2011,A1 .

7
[ 99873-30-0 ]
[ 1279015-59-6 ]

References: [1]Patent: WO2011/34828,2011,A1 .

8
[ 99873-30-0 ]
[ 76513-69-4 ]
{2-[(4-bromo-3-ethylphenoxy)methoxy]ethyl}(trimethyl)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18.0h;	Preparation 344(2-((4-l3romo-3-ethylphenoxy)methoxy)ethyl)trim- ethylsilane10778] To a solution of <strong>[99873-30-0]4-bromo-3-ethylphenol</strong> (9 g, 44.8 mmol) in DCM (100 mE) was added DIPEA (8.6 mE, 49.3 mmol) followed by SEMCI (8.73 mE, 49.3 mmol) and the reaction was stirred at room temperature for 18 hours. The reaction was washed with water, 1 N aqueous HC1 solution and saturated aqueous sodium hydrogen carbonate solution, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 3% EtOAc in hexanes to afford the title compound. ?H NMR (400 MHz, CDC13): oe ppm 0.00 (s, 9H), 0.90 (m, 2H), 1.25 (m, 3H), 2.75 (m, 2H), 3.75 (m, 2H), 5.20 (s, 2H), 6.80 (m, 1H), 7.00 (d, 1H), 7.40 (d, 1H).

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 767 - 786.
[2]Patent: US2015/329542,2015,A1 .Location in patent: Paragraph 0778.

9
[ 99873-30-0 ]
6-(2-ethyl-4-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-c]pyridin-4-yl trifluoromethanesulfonate [ No CAS ]

References: [1]Patent: US2015/329542,2015,A1 .

10
[ 99873-30-0 ]
6-(2-ethyl-4-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-c]pyridin-4-ol [ No CAS ]

References: [1]Patent: US2015/329542,2015,A1 .

11
[ 99873-30-0 ]
6-(2-ethyl-4-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-c]pyridine 5-oxide [ No CAS ]

References: [1]Patent: US2015/329542,2015,A1 .

12
[ 99873-30-0 ]
6-(2-ethyl-4-((2-(trimethylsilyl)ethoxy)methoxy)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-c]pyridine [ No CAS ]

References: [1]Patent: US2015/329542,2015,A1 .

13
[ 99873-30-0 ]
(2-[3-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methoxy}ethyl)(trimethyl)silane [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 767 - 786.
[2]Patent: US2015/329542,2015,A1 .

14
[ 99873-30-0 ]
4-[4-(7,8-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]-3-ethylphenol formate [ No CAS ]

References: [1]Patent: US2015/329542,2015,A1 .

15
[ 99873-30-0 ]
1-{2-(bromomethyl)-3-methylphenyl}-4-methyl-1,4-dihydro-5H-tetrazol-5-one [ No CAS ]
1-[2-(4-bromo-3-ethylphenoxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.77 g	With potassium carbonate; In acetonitrile; at 80℃; for 4.0h;	A mixture of 2.83g of 14A (mentioned in the Reference Preparation Example 14), 2.01g of 45A (mentioned in the Reference Preparation Example 45), 2.76g of potassium carbonate, and 40mL of acetonitrile was heated and stirred at 80C for 4 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue thus obtained was washed with methyl tert-butyl ether and hexane to obtain 3.77g of 1-[2-(4-bromo-3-ethylphenoxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (Referred to as 47A).
3.77 g	With potassium carbonate; In acetonitrile; at 80℃; for 4.0h;	Reference Production Example 47 (0711) A mixture of 2.83 g of 14A mentioned in Reference Production Example 14, 2.01 g of 45A mentioned in Reference Production Example 45, 2.76 g of potassium carbonate, and 40 mL of acetonitrile was stirred with heating at 80 C. for 4 hours. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was washed with hexane and methyl tert-butyl ketone to obtain 3.77 g of 1-[2-(4-bromo-3-ethylphenoxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (referred to as 47A). (0712) 1H-NMR (CDCl3) delta: 7.44-7.36 (3H, m), 7.28 (1H, dd, J=7.1, 2.1 Hz), 6.70-6.66 (2H, m), 5.14 (2H, s), 3.68 (3H, s), 2.57 (2H, q, J=7.6 Hz), 2.55 (3H, s), 1.20 (3H, t, J=7.6 Hz).

References: [1]Patent: CN105392779,2016,A .Location in patent: Paragraph 1359; 1360; 1361; 1362.
[2]Patent: US2016/159755,2016,A1 .Location in patent: Paragraph 0711; 0712.

16
[ 99873-30-0 ]
6-(2-ethyl-4-[2-(trimethylsilyl)ethoxy]methoxy}phenyl)-3-(1H-imidazol-2-yl)-1-[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole [ No CAS ]