[ CAS No. 83902-02-7 ] {[proInfo.proName]}

Name: 83902-02-7|2-(Bromomethyl)-1,3-dimethylbenzene|97%
Brand: Ambeed
SKU: A162489
Price: 37.0 USD
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Quality Control of [ 83902-02-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 83902-02-7 ]

Product Details of [ 83902-02-7 ]

CAS No. :	83902-02-7	MDL No. :	MFCD03844742
Formula :	C₉H₁₁Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PSRARXVEBZQEML-UHFFFAOYSA-N
M.W :	199.09	Pubchem ID :	13929124
Synonyms :

Calculated chemistry of [ 83902-02-7 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.21
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.41
Log Po/w (XLOGP3) :	3.21
Log Po/w (WLOGP) :	3.05
Log Po/w (MLOGP) :	3.71
Log Po/w (SILICOS-IT) :	3.77
Consensus Log Po/w :	3.23

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.47
Solubility :	0.0667 mg/ml ; 0.000335 mol/l
Class :	Soluble
Log S (Ali) :	-2.88
Solubility :	0.261 mg/ml ; 0.00131 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.43
Solubility :	0.00735 mg/ml ; 0.0000369 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.61

Safety of [ 83902-02-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 83902-02-7 ]

* 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 [ 83902-02-7 ]
Downstream synthetic route of [ 83902-02-7 ]

[ 83902-02-7 ] Synthesis Path-Upstream 1~4

1
[ 62285-58-9 ]
[ 83902-02-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 12, p. 2167 - 2178
[2] Canadian Journal of Chemistry, 1986, vol. 64, p. 1060 - 1071
[3] Tetrahedron, 2001, vol. 57, # 30, p. 6375 - 6382
[4] Australian Journal of Chemistry, 2009, vol. 62, # 7, p. 700 - 710
[5] Acta Chemica Scandinavica (1947-1973), 1963, vol. 17, p. 1252 - 1261
[6] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 21, p. 9498 - 9510
[7] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 23, p. 5571 - 5577

2
[ 632-46-2 ]
[ 83902-02-7 ]

Reference： [1] Tetrahedron, 2001, vol. 57, # 30, p. 6375 - 6382
[2] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 12, p. 2167 - 2178
[3] Canadian Journal of Chemistry, 1986, vol. 64, p. 1060 - 1071
[4] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 23, p. 5571 - 5577

3
[ 576-22-7 ]
[ 83902-02-7 ]

Reference： [1] Acta Chemica Scandinavica (1947-1973), 1963, vol. 17, p. 1252 - 1261

4
[ 83902-02-7 ]
[ 938-50-1 ]

Reference： [1] Acta Chemica Scandinavica (1947-1973), 1963, vol. 17, p. 1252 - 1261

[ 83902-02-7 ] Synthesis Path-Downstream 1~88

1
[ 83902-02-7 ]
[ 143-33-9 ]
[ 54708-14-4 ]

Reference： [1]Acta Chemica Scandinavica (1947),1963,vol. 17,p. 1252 - 1261
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 2243 - 2251

2
[ 62285-58-9 ]
[ 83902-02-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With pyridine; phosphorus tribromide; In dichloromethane; at 0℃; for 2h;	[0484] To a solution of (2,6-dimethyl-phenyl)-methanol (13.6 g, 100.00 mmol) in DCM (400 mL) was added PBr3 (5.7 g, 150.0 mmol) and pyridine (0.5 mL). The mixture was stirred at 0 C for 2 hrs. TLC showed the reaction was completed. The reaction was quenched with slow addition of ice water (50 mL). The aqueous phase was extracted with DCM (300 mL x3). The organic layer was washed with brine (500 mL), dried over Na2S04 and concentrated to give 2-bromom ethyl- 1,3 -dimethyl -benzene (19.1 g, yield: 96 %) as a yellow solid.
	With phosphorus tribromide; In dichloromethane; at 0 - 20℃; for 1h;	General procedure: To a solution of various benzyl alcohols 17a-17n (7.50 mmol) in anhydrous dichloromethane (40 ml) was added PBr3 (0.84 ml, 9.0 mmol) slowly at 0 oC. The reaction mixture was stirred at room temperature for 1.0 h and then added NaHCO3 (aq) to pH = 6-7. The organic layer was washed with brine, dried over Na2SO4 and condensed. The crude product was obtained as light brown oils and used directly for the next step without further purification.

Reference： [1]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 2167 - 2178
[2]Patent: WO2019/32720,2019,A1 .Location in patent: Paragraph 0483-0484
[3]Canadian Journal of Chemistry,1986,vol. 64,p. 1060 - 1071
[4]Tetrahedron,2001,vol. 57,p. 6375 - 6382
[5]Australian Journal of Chemistry,2009,vol. 62,p. 700 - 710
[6]Acta Chemica Scandinavica (1947),1963,vol. 17,p. 1252 - 1261
[7]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 9498 - 9510
[8]Journal of Agricultural and Food Chemistry,2015,vol. 63,p. 5571 - 5577
[9]European Journal of Medicinal Chemistry,2019,vol. 163,p. 864 - 882
[10]Patent: EP1736467,2006,A1

3
[ 53156-46-0 ]
[ 83902-02-7 ]
[ 104308-17-0 ]

Reference： [1]Canadian Journal of Chemistry,1986,vol. 64,p. 1060 - 1071

4
[ 83902-02-7 ]
[ 94451-06-6 ]
[ 94450-93-8 ]
[ 94451-09-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 1479 - 1486

5
[ 83902-02-7 ]
(2-Bromo-9H-fluoren-9-yl)-dimethyl-amine [ No CAS ]
(2-Bromo-9H-fluoren-9-yl)-(2,6-dimethyl-benzyl)-dimethyl-ammonium; bromide [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1986,vol. 64,p. 1060 - 1071

6
[ 83902-02-7 ]
[ 138566-17-3 ]
[ 187829-92-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 2167 - 2178

7
[ 83902-02-7 ]
[ 81477-94-3 ]
(R)-tert-butyl N-(diphenylmethylene)-2,6-dimethylphenylalaninate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 5139 - 5151

8
[ 106-25-2 ]
[ 83902-02-7 ]
2-((Z)-3,7-Dimethyl-octa-2,6-dienyloxymethyl)-1,3-dimethyl-benzene [ No CAS ]

Reference： [1]Synthesis,2004,p. 692 - 700

9
[ 106-24-1 ]
[ 83902-02-7 ]
2-((E)-3,7-Dimethyl-octa-2,6-dienyloxymethyl)-1,3-dimethyl-benzene [ No CAS ]

Reference： [1]Synthesis,2004,p. 692 - 700

10
[ 51887-25-3 ]
[ 83902-02-7 ]
1,3-dimethyl-2-tridec-2-ynyloxymethyl-benzene [ No CAS ]

Reference： [1]Synthesis,2004,p. 692 - 700

11
[ 103-16-2 ]
[ 83902-02-7 ]
2-(4-Benzyloxy-phenoxymethyl)-1,3-dimethyl-benzene [ No CAS ]

Reference： [1]Synthesis,2004,p. 692 - 700

12
[ 83902-02-7 ]
[ 41884-32-6 ]
[ 699008-01-0 ]

Reference： [1]Synthesis,2004,p. 692 - 700

13
[ 83902-02-7 ]
[ 756533-18-3 ]
4-Methoxy-benzoic acid (3S,4R)-4-[4-(2,6-dimethyl-benzyloxy)-benzenesulfonyl]-3-hydroxy-tetrahydro-pyran-3-ylmethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4727 - 4730

14
[ 24424-99-5 ]
[ 83902-02-7 ]
Ni(II) complex of the Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone [ No CAS ]
[ 96293-17-3 ]
[ 126312-57-0 ]

Reference： [1]Heterocycles,2004,vol. 64,p. 505 - 514

15
[ 83902-02-7 ]
[ 81477-94-3 ]
2-(benzhydrylidene-amino)-3-(2,6-dimethyl-phenyl)-propionic acid <i>tert</i>-butyl ester [ No CAS ]
(R)-tert-butyl N-(diphenylmethylene)-2,6-dimethylphenylalaninate [ No CAS ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 11425 - 11436

16
[ 17767-81-6 ]
[ 83902-02-7 ]
N-phenyl-2-hydroxy-3-(2,6-dimethylphenyl)-2-phenylpropionamide [ No CAS ]
N-phenyl-2-hydroxy-3-(2,6-dimethylphenyl)-2-phenylpropionamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 3839 - 3842

17
[ 83902-02-7 ]
4-(2',6'-dimethyl)benzyloxyphenol [ No CAS ]

Reference： [1]Synthesis,2004,p. 692 - 700

18
[ 83902-02-7 ]
4-(2',6'-dimethylbenzyl)oxytetradecane [ No CAS ]

Reference： [1]Synthesis,2004,p. 692 - 700

19
[ 632-46-2 ]
[ 83902-02-7 ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 6375 - 6382
[2]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 2167 - 2178
[3]Canadian Journal of Chemistry,1986,vol. 64,p. 1060 - 1071
[4]Journal of Agricultural and Food Chemistry,2015,vol. 63,p. 5571 - 5577
[5]European Journal of Medicinal Chemistry,2019,vol. 163,p. 864 - 882
[6]Patent: WO2019/32720,2019,A1

20
[ 83902-02-7 ]
[ 1026631-02-6 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 2243 - 2251

21
[ 83902-02-7 ]
[ 54707-85-6 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 2243 - 2251

22
[ 83902-02-7 ]
[ 126312-57-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 2167 - 2178

23
[ 83902-02-7 ]
[ 103854-26-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 2167 - 2178

24
[ 83902-02-7 ]
(S)-2-Amino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(2,6-dimethyl-phenyl)-propan-1-one; hydrochloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 2167 - 2178

25
[ 83902-02-7 ]
[ 104308-11-4 ]

Reference： [1]Canadian Journal of Chemistry,1986,vol. 64,p. 1060 - 1071

26
[ 83902-02-7 ]
[ 104308-16-9 ]

Reference： [1]Canadian Journal of Chemistry,1986,vol. 64,p. 1060 - 1071

27
[ 83902-02-7 ]
[ 104308-18-1 ]

Reference： [1]Canadian Journal of Chemistry,1986,vol. 64,p. 1060 - 1071

28
[ 83902-02-7 ]
[ 104308-25-0 ]

Reference： [1]Canadian Journal of Chemistry,1986,vol. 64,p. 1060 - 1071

29
[ 576-22-7 ]
[ 83902-02-7 ]

Reference： [1]Acta Chemica Scandinavica (1947),1963,vol. 17,p. 1252 - 1261

30
[ 83902-02-7 ]
[ 69385-86-0 ]

Reference： [1]Acta Chemica Scandinavica (1947),1963,vol. 17,p. 1252 - 1261

31
[ 83902-02-7 ]
[ 91552-37-3 ]

Reference： [1]Acta Chemica Scandinavica (1947),1963,vol. 17,p. 1252 - 1261

32
[ 83902-02-7 ]
[ 938-50-1 ]

Reference： [1]Acta Chemica Scandinavica (1947),1963,vol. 17,p. 1252 - 1261

33
[ 83902-02-7 ]
[ 97021-64-2 ]

Reference： [1]Acta Chemica Scandinavica (1947),1963,vol. 17,p. 1252 - 1261

34
[ 83902-02-7 ]
[ 92725-73-0 ]

Reference： [1]Acta Chemica Scandinavica (1947),1963,vol. 17,p. 1252 - 1261

35
[ 910777-75-2 ]
[ 83902-02-7 ]
2-(8-([(2,6-dimethylphenyl)methyl]oxy)-2,3-dimethylimidazo[1,2-a]pyridin-6-yl)-3(2H)-pyridazinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h;	Example 80.; 2-(8-[(2,6-Dimethylphenyl)methyI]oxy}-2,3-dimethyIimidazo[l,2-«]pyridiii-6-yl)-3(2/Z)-pyridazmoneTo a solution of 2-(8-hydroxy-2,3-dimethylimidazo[l,2-alpha]pyridin-6-yl)-3(2/i)- pyridazinone (175 mg, 0.68 mmol; Description 48) in dimethylformamide (5 mL) was added potassium carbonate (190 mg, 1.38 mmol) and <strong>[83902-02-7]2,6-dimethylbenzyl bromide</strong> (170 mg, 0.85 mmol). The mixture was stirred at room temperature for 2 hours under argon and then loaded onto an Isolute SCX cartridge. Elution with methanol, then 2M NH3 in methanol gave, after evaporation, the crude product which was purified by silica gel chromatography eluting with ethyl acetate to yield the title compound. MS (ES+ve): [M+H]+ at m/z 375 (C22H22N4 O2 requires [M+H]+ at m/z 375).

Reference： [1]Patent: WO2006/100119,2006,A1 .Location in patent: Page/Page column 88

36
[ 910778-84-6 ]
[ 83902-02-7 ]
5-(8-([(2,6-dimethylphenyl)methyl]amino)-2,3-dimethylimidazo[1,2-a]pyridin-6-yl)-2(1H)-pyridinone hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 95;. 5-(8-[(2,6-Dimethylphenyl)methyl]amino}-2,3- dimethylimidazo [1 ,2-alpha] pyridin-6-yl)-2(ll?)-pyridinone hydrochloride EPO <DP n="98"/>A mixture of N-[(2,6-dimethylphenyl)methyl]-2,3-dimethyl-6-[6-(metliyloxy)-3- pyridinyl]imidazo[l,2-alpha]pyridin-8-amme (106.8 mg, 0.276 mmol; Example 94) and 5N HCl (5 ml) was heated under reflux overnight. The cooled reaction mixture was evaporated to dryness. The residue was dissolved in methanol and water and loaded onto an Isolute SCX cartridge, elution with methanol, then IM NH3 in methanol gave 5-(8-amino-2,3-dimethylimidazo[l,2-alpha]pyridin-6-yl)-2(lH)-pyridinone; MS (ES+ve): [M+Eta]+ at m/z 255 (C14H14N4O requires [M+H]+ at m/z 255). This intermediate (60 mg, 0.23 mmol) was dissolved in dimethylformamide (3 ml), 2,6- dimethylbenzyl bromide (45 mg, 0.23 mmol) and sodium carbonate (48 mg, 0.45 mmol) were added and the mixture stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. And further extracted with ethyl acetate. The organic phase was washed with water, then brine, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica gel (ethyl acetate/methanol). The product was dissolved in methanol/water/2N HCl (15:35:2 ml) and then loaded onto a 1Og tC18 Sep-Pak cartridge and eluted with a gradient up to methanol/water/2N HCl (65:35:0.5). Evaporation gave the title compound as a white solid. MS (ES+ve): [M+H]+ at m/z 373 (C23H24N4O requires [M+H]+ at m/z 373).

Reference： [1]Patent: WO2006/100119,2006,A1 .Location in patent: Page/Page column 96-97

37
[ 910777-62-7 ]
[ 83902-02-7 ]
1-(8-([(2,6-dimethylphenyl)methyl]oxy)-2-methylimidazo[1,2-a]pyridin-6-yl)-2(1H)-pyridinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3.5h;	Description 38:; l-(8-[(2,6-dimethylphenyl)methyl]oxy}-2-methylimidazo[l,2- alpha]pyridin-6-yl)-2(l/-0-pyridinoneTo a suspension of l-(8-hydroxy-2-methylimidazo[l,2-alpha]pyridin-6-yl)-2(lH)- pyridinone trifluoroacetic acid salt (Description 37, 1.9 g, 5.4 mmol) and potassium carbonate (3 g, 21.6 mmol) in dimethylformamide (35 ml) was added 2-(bromomethyl)-l,3-dimethylbenzene (1.3 g, 6.5 mmol) and the resulting suspension was stirred at room temperature for 3 hours. Potassium carbonate (0.6 g, 4.3 mmol) and 2-(bromomethyl)-l,3-dimethylbenzene (0.26 g, 1.3 mmol) were then added and the solution stirred for another 30 minutes. The mixture was partitioned between water and ethyl acetate and the two phases were separated. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed three times with a saturated aqueous sodium bicarbonate, dried (MgSO4) and concentrated in vacuo. The residue was triturated with hexane to give the title compound (1.68 g, 86%) as a white solid. MS (ES+ve): [M+Eta]+ at m/z 360 (C22H21N3O2 requires [M+H]+ at m/z 360).

Reference： [1]Patent: WO2006/100119,2006,A1 .Location in patent: Page/Page column 36

38
[ 83902-02-7 ]
(2,6-dimethylphenyl)methanesulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of <strong>[83902-02-7]2-(bromomethyl)-1,3-dimethylbenzene</strong> (300 mg, 1.52 mmol) and sodium sulfite (Na2SO3, 191 mg, 1.52 mmol) in 1,4-dioxane (5 mL) -water (5 mL) was heated under reflux for 5 hours. The solvent was evaporated, and the resulting sulfonate was washed with ethyl acetate and dissolved in 4N hydrogen chloride/ 1,4-dioxane solution (10 mL). The precipitated salt was collected by filtration and the solvent was evaporated under reduced pressure to give the title compound 136 mg as pale brown crystals. 1H-NMR delta (DMSO-d6); 2.38 (6H, s), 3.36 (1H, s), 3.88 (2H, s), 6.92-6.94 (3H, m).

Reference： [1]Patent: EP1736467,2006,A1 .Location in patent: Page/Page column 46

39
[ 918798-16-0 ]
[ 83902-02-7 ]
1-(8-[(2,6-dimethylphenyl)methyl]amino}-2,3-dimethylimidazo[1,2-a]pyridin-6-yl)-2-piperidinone hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 6. l-(8-{\|(2,6-Dimethylphenyl)methyl]amino}-2,3-dimethyHmidazo[l,2-alpha]pyridin-6- yl)-2-piperidinone hydrochlorideTo a solution of l-(8-amino-2,3-dimethylimidazo[l,2-alpha]pyridin-6-yl)-2-piperidinone (81.2 mg, 0.314 mmol; Description 3) in dimethylformamide (4 mL) was added sodium carbonate (83 mg, 0.783 mmol) and <strong>[83902-02-7]2,6-dimethylbenzyl bromide</strong> (78 mg, 0.392 mmol). The mixture was stirred at room temperature for 20 hours, and then partitioned between ethyl acetate and water. The organic phase was washed with water, then brine, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica gel (ethyl acetate/methanol). The product was dissolved in methanol (3 mL), water (1 mL) and 2N HCl (0.2 mL) were added. After stirring for 5 minutes, the solution was evaporated to give the title compound as a buff solid. MS (ES+ve): [M+H]+ at m/z 311 (C23H28N4O requires [M+H]+ at m/z 377).

Reference： [1]Patent: WO2007/3386,2007,A1 .Location in patent: Page/Page column 22

40
[ 918798-27-3 ]
[ 83902-02-7 ]
(4S)-1-(8-[(2,6-dimethylphenyl)methyl]oxy}-2,3-dimethylimidazo[1,2-a]pyridin-6-yl)-4-hydroxy-2-pyrrolidinone hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 14 (4S)-l-(8-[(2,6-Dimethylphenyl)methyl]oxy}-2,3-dimethylimidazo[l,2-alpha]pyridin- 6-yl)-4-hydroxy-2-pyrrolidinone hydrochloride EPO <DP n="28"/>A mixture of potassium carbonate (52 mg, 0.38 mmol), (4S)-4-hydroxy-l-(8-hydroxy- 2,3-dimethylimidazo[l,2-alpha]pyridin-6-yl)-2-pyrrolidinone (66 mg, 0.25 mmol; Description 11) and <strong>[83902-02-7]2,6-dimethylbenzyl bromide</strong> (60 mg, 0.3 mmol) in dimethylformamide (2 mL) was stirred under argon at ambient temperature for 3 hours. The mixture was applied to an Isolute SCX cartridge and eluted with methanol followed by 2M NH3 in methanol. The basic fractions were combined and evaporated under reduced pressure. This residue was purified by column chromatography on silica eluting with a hexane to ethyl acetate to 10% methanol in ethyl acetate gradient to afford the free base of the title compound after evaporation under reduced pressure. This was dissolved in dichloromethane (2 mL), and then IM HCl in diethyl ether (0.3 mL) was added. The solvents were evaporated, to give the title compound; MS (ES+ve): [M+H]+ at m/z 380 (C22H25N3O3 requires [M+H]+ at m/z 380).

Reference： [1]Patent: WO2007/3386,2007,A1 .Location in patent: Page/Page column 26-27

41
[ 918798-31-9 ]
[ 83902-02-7 ]
4-(8-[(2,6-dimethylphenyl)methyl]oxy}-2,3-dimethylimidazo[1,2-a]pyridin-6-yl)-3-morpholinone hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 154-(8-[(2,6-dimethylphenyl)methyl]oxy}-2,3-dimethylimidazo[l,2-alpha]pyridiii-6-yl)- ochlorideA mixture of potassium carbonate (143 mg, 1.04 mmol), 4-(8-hydroxy-2,3- dimethylimidazo[l,2-alpha]pyridin-6-yl)-3-morpholinone (180 mg, 0.69 mmol; Description 13) and <strong>[83902-02-7]2,6-dimethylbenzyl bromide</strong> (165 mg, 0.83 mmol) in dimethylformamide (5 mL) was stirred under argon at ambient temperature overnight. The mixture was applied to an Isolute SCX cartridge and washed with methanol followed by elution with 2M NH3 in methanol. The basic fractions were combined and evaporated under reduced pressure. This residue was purified by column chromatography on silica eluting with a hexane to ethyl acetate gradient, evaporated under reduced pressure and dissolved in dichloromethane (2 mL). 1.0M ethereal HCl was added (0.5 mL) and the solution evaporated under reduced pressure to yield the EPO <DP n="29"/>title compound; MS (ES+ve): [M+H]+ at m/z 380 (C22H25N3O3 requires [M+H]+ at m/z 380).

Reference： [1]Patent: WO2007/3386,2007,A1 .Location in patent: Page/Page column 27-28

42
C₁₀H₁₄O₂S [ No CAS ]
[ 83902-02-7 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium bromide; In dichloromethane; at 0 - 20℃; for 2h;	To a solution of 2,6-dimethylbenzyl alcohol (456 mg, 3.35 mmol) and triethylamine (0.560 mL, 4.02 mmol) in dichloromethane (CH2Cl2, 15 mL) was added methanesulfonyl chloride (0.258 mL, 3.68 mmol) under ice-cooling and the mixture was stirred for one hour. Thereto was subsequently added lithium bromide (LiBr, 582 mg, 6.70 mmol) under ice-cooling, and the mixture was warmed to room temperature and the mixture was stirred for 2 hours. Thereto was added water to quench the reaction and the reactant was extracted with ethyl acetate and the organic layer was washed twice with water. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the title compound 364 mg as colorless oils. 1H-NMR delta (DMSO-d6); 2.37 (6H, s), 4.71 (2H, s), 7.04-7.16 (3H, m).

Reference： [1]Patent: EP1736467,2006,A1 .Location in patent: Page/Page column 46

43
[ 24101-91-5 ]
[ 83902-02-7 ]
[ 1093231-96-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 9498 - 9510

44
[ 83902-02-7 ]
[ 32685-16-8 ]
[ 1207534-51-7 ]

Reference： [1]Australian Journal of Chemistry,2009,vol. 62,p. 700 - 710

45
[ 2973-77-5 ]
[ 83902-02-7 ]
[ 1207104-52-6 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 1359 - 1370

46
[ 1257420-89-5 ]
[ 83902-02-7 ]
[ 1257421-13-8 ]
(S)-5-(2,6-dimethylbenzyl)-2,2-dimethyl-5-((triphenylsilyl)ethynyl)-1,3-dioxolan-4-one [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 7593 - 7595

47
C₄₃H₄₂Cl₂N₃O₅Pol [ No CAS ]
[ 83902-02-7 ]
C₅₂H₅₂Cl₂N₃O₅Pol [ No CAS ]

Reference： [1]Organic Letters,2009,vol. 11,p. 3558 - 3561

48
[ 1005036-25-8 ]
[ 83902-02-7 ]
[ 1338224-93-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5774 - 5777

49
[ 83902-02-7 ]
[ 66317-38-2 ]
[ 1338225-27-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5774 - 5777

50
[ 73260-12-5 ]
[ 83902-02-7 ]
3-acetyl-1-(2,6-dimethylbenzyl)-4-methoxy-1H-indole [ No CAS ]

Reference： [1]Molecules,2011,vol. 16,p. 6858 - 6870

51
[ 83902-02-7 ]
[ 1351646-21-3 ]

Reference： [1]Molecules,2011,vol. 16,p. 6858 - 6870

52
[ 83902-02-7 ]
[ 1351646-51-9 ]

Reference： [1]Molecules,2011,vol. 16,p. 6858 - 6870

53
[ 1471996-62-9 ]
[ 83902-02-7 ]
[ 1471996-69-6 ]

Yield	Reaction Conditions	Operation in experiment
		{(S)-6-[(R)-5-cyano-4-(2,6-dimethyl-benzyl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester A flask charged with a stir bar and anhydrous LiCl (49 mg) is heated to 180 C. under high vacuum (ca. 1 mbar). After 30 min the flask is cooled to room temperature, filled with Ar, and Zn powder (84 mg) is added under Ar atmosphere. The flask is reevacuated (ca. 1 mbar) and heated to 180 C. After another 30 min the flask is cooled to room temperature and filled with Ar again. Tetrahydrofuran (dry, 0.5 mL) is added and the Zn is activated with 1,2-dibromoethane (2 muL) and trimethylsilyl chloride (1.5 muL) (for comparison see e.g. Synthesis 2009, 681-6). A solution of <strong>[83902-02-7]2,6-dimethylbenzyl bromide</strong> (0.23 g) in tetrahydrofuran (dry, 2 mL) is added dropwise. The mixture is stirred for 30 min prior to addition of {(S)-6-[(R)-4-bromo-5-cyano-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (0.10 g) in tetrahydrofuran (dry, 2 mL) and [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]-(3-chloropyridyl)-palladium(II) dichloride (Pd-PEPPSI-IPr, 20 mg). The mixture is heated to 60 C. and stirred at this temperature overnight. After cooling to room temperature, aqueous NH4Cl solution is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (MgSO4) and concentrated. The residue is purified by HPLC on reversed phase (MeCN/water/NH4OH) to give the title compound. LC (method 4): tR=1.28 min; Mass spectrum (ESI+): m/z=468 [M+H]+.
		A flask charged with a stir bar and anhydrous LiCI (49 mg) is heated to 180 C under high vacuum (ca. 1 mbar). After 30 min the flask is cooled to room temperature, filled with Ar, and Zn powder (84 mg) is added under Ar atmosphere. The flask is reevacuated (ca. 1 mbar) and heated to 180 C. After another 30 min the flask is cooled to room temperature and filled with Ar again. Tetrahydrofuran (dry, 0.5 ml_) is added and the Zn is activated with 1 ,2-dibromoethane (2 muIota_) and trimethylsilyl chloride (1 .5 muIota_) (for comparison see e.g. Synthesis 2009, 681 -6). A solution of 2,6- dimethylbenzyl bromide (0.23 g) in tetrahydrofuran (dry, 2 ml_) is added dropwise. The mixture is stirred for 30 min prior to addition of {(S)-6-[(R)-4-bromo-5-cyano- indan-1 -yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (0.10 g) in tetrahydrofuran (dry, 2 ml_) and [1 ,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]-(3- chloropyridyl)-palladium(ll) dichloride (Pd-PEPPSI-IPr, 20 mg). The mixture is heated to 60 C and stirred at this temperature overnight. After cooling to room temperature, aqueous NH CI solution is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (MgSO4) and concentrated. The residue is purified by H PLC on reversed phase (MeCN/water/NH OH) to g ive th e titl e compound. LC (method 4): tR = 1 .28 min; Mass spectrum (ESI+): m/z = 468 [M+H]+.

Reference： [1]Patent: US2013/289074,2013,A1 .Location in patent: Paragraph 0198; 0199
[2]Patent: WO2013/164292,2013,A1 .Location in patent: Page/Page column 56

54
[ 83902-02-7 ]
[ 95-54-5 ]
[ 1608149-16-1 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 4727 - 4734

55
[ 83902-02-7 ]
[ 95-54-5 ]
[ 953072-17-8 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 4727 - 4734

56
[ 83902-02-7 ]
9-pseudoaglycone of spinosyn D [ No CAS ]
C₄₂H₆₁NO₆ [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2015,vol. 63,p. 5571 - 5577

57
[ 1276122-45-2 ]
[ 83902-02-7 ]
2‐{2‐[(2,6‐dimethylphenyl)methoxy]phenyl}‐[1,3]oxazolo[5,4‐b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile;	General procedure: The mixture of 3-aminopyridin-2-ol (1.05 eq) and 2-(trifluoromethyl)phenol (1.0 eq) in 1.0 mol/L NaOH aqueous solution (4.0 eq) was heated under 80C for 2 to 4 hours depending on the reaction speed. After the reaction was finished, water and dichloromethane were added to the reaction mixture to extract the product. The organic phase was washed twice with saturated brine, dried over anhydrous sodium sulfate and distilled to remove dichloromethane. The crude product was purified by column chromatography purification to gain 2-(oxazolo[5,4-b]pyridin-2-yl)phenol (QY-OH). Then the intermediate QY-OH (1.0 eq) and corresponding substituted (bromomethyl)benzene (1.2 eq) were dissolved in acetonitrile with the existence of anhydrous potassium carbonate (2.0 eq). The reaction temperature was depended on the reaction speed. The solvent acetonitrile was removed after the reaction was completed, and the crude product was extracted and purified by column chromatography to gain the target compounds QY2. QY1 and QY33 were obtained with the same method, only to change the reactants from 3-aminopyridin-2-ol to 2-aminophenol or from 2-(trifluoromethyl)phenol to 4-(trifluoromethyl)phenol. Reactants used are listed in Supporting Table 1.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 3511 - 3515

58
[ 930-30-3 ]
[ 593-71-5 ]
[ 83902-02-7 ]
1-(2,6-dimethylbenzyl)-2-cyclopentene-1-carbaldehyde [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 12677 - 12682
Angew. Chem.,2017,vol. 129,p. 12851 - 12856,6

59
C₃₄H₄₁N₆O₅Pol [ No CAS ]
[ 83902-02-7 ]
C₄₃H₅₁N₆O₅Pol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 9263 - 9274

60
C₃₄H₄₁N₆O₅Pol [ No CAS ]
[ 83902-02-7 ]
C₃₈H₄₄N₆O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 9263 - 9274

61
[ 83902-02-7 ]
C₁₈H₁₆BrF₂N₃OS [ No CAS ]
C₂₇H₂₇F₂N₃OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With palladium diacetate; zinc; ruphos; In tetrahydrofuran; at 40 - 100℃; for 0.166667h;Microwave irradiation;	A solution of <strong>[83902-02-7]2,6-dimethylbenzyl bromide</strong> (33.91 mg, 017 mmol) in THF (0.35 mL) was pumped using the R2 + R4 through a column containing activated Zinc at 0.5ml/min at 40 C. The outcome was collected into a solution of intermediate 12 (25 mg,0.057 mmol), Palladium(II) acetate (0.64 mg, 0.003 mmol), RuPhos (2.65 mg, 0.006 mmol) in THF (0.25 mL) and heated in a microwave oven for 10 mm at 100 C. The mixture was quenched with 10% NH4C1 and extracted with EtOAc. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated. The residue was purified by column chromatography (silica, EtOAc/DCM 0/100 to 100/0). Desired fractions were collected and the solvent evaporated to yield crude compound 9, whichwas further purified by RP HPLC (Stationary phase: C18 Sunfire 30 x 100 mm 5 jim, mobile phase: NH4HCO3/CH3CN) to yield compound 9 (9 mg, 33%) as an off white foam.

Reference： [1]Patent: WO2018/162444,2018,A1 .Location in patent: Page/Page column 33; 34

62
[ 83902-02-7 ]
3-(pyridin-3-ylamino)benzo[d]isoxazol-4-ol [ No CAS ]
4-((2,6-dimethylbenzyl)oxy)-N-(pyridin-3-yl)benzo[d]isoxazol-3-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 8241 - 8254

63
[ 83902-02-7 ]
[ 118623-71-5 ]
2-((2,6-dimethyl)benzyloxy)-N-(pyridin-3-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78.4%	With potassium carbonate; potassium iodide; In acetone; at 20℃; for 1h;	General procedure: To a solution of 12 (0.21 g, 1.0 mmol) in acetone (6 ml) was added various benzyl bromides 18k-18x (1.0 mmol), K2CO3 (0.28 g,2.0 mmol) and catalytic KI. The reaction mixture was stirred at room temperature for 1.0 h and then evaporated the solvent. The residue was extracted by ethyl acetate, washed with brine and dried over Na2SO4. After the organic solvent was evaporated, the crude product was purified by flash chromatograph eluting with ethyl acetate/petroleum ether (1:2, v: v) to afford 22, 29, 30, 33 and 36-45.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 163,p. 864 - 882

64
C₁₀H₁₄O₃S [ No CAS ]
[ 83902-02-7 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium bromide; In dichloromethane; at 0 - 20℃; for 2h;	To a solution of 2,6-dimethylbenzyl alcohol (456 mg, 3.35 mmol) and triethylamine (0.560 mL, 4.02 mmol) in dichloromethane (CH2Cl2, 15 mL) was added methanesulfonyl chloride (0.258 mL, 3.68 mmol) under ice-cooling and the mixture was stirred for one hour. Thereto was subsequently added lithium bromide (LiBr, 582 mg, 6.70 mmol) under ice-cooling, and the mixture was warmed to room temperature and the mixture was stirred for 2 hours. Thereto was added water to quench the reaction and the reactant was extracted with ethyl acetate and the organic layer was washed twice with water. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the title compound 364 mg as colorless oils. 1H-NMR delta (DMSO-d6); 2.37 (6H, s), 4.71 (2H, s), 7.04-7.16 (3H, m).

Reference： [1]Patent: EP1736467,2006,A1 .Location in patent: Page/Page column 46

65
[ 83902-02-7 ]
[ 867262-52-0 ]

Reference： [1]Patent: EP1736467,2006,A1

66
[ 83902-02-7 ]
[ 540524-67-2 ]

Reference： [1]Patent: EP1736467,2006,A1

67
potassium cyanide [ No CAS ]
[ 83902-02-7 ]
[ 54708-14-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	In N,N-dimethyl-formamide; at 50℃;	[0486] A suspension of 2-bromomethyl-l,3-dimethyl-benzene (18.5 g, 92.50 mmol), KCN (9.0 g, 138.75 mmol) in a solution of DMF (100 mL) was stirred at 50 C overnight. TLC showed the reaction was completed. The solvent was removed in vacuum. Water (100 mL) was added. The mixture was extracted with DCM (200 mL x3). The organic layer was washed with brine (500 mL), dried over Na2S04 and concentrated to give (2,6-dimethyl- phenyl)-acetonitrile (13.5 g, yield: 81 %) as a yellow oil. [0487] 1H MR (400 MHz, CDC13): delta = 7.16-6.99 (m, 3H), 3.63 (s, 2H), 2.39 (s, 6H).

Reference： [1]Patent: WO2019/32720,2019,A1 .Location in patent: Paragraph 0485-0487

68
[ 14920-81-1 ]
[ 83902-02-7 ]