[ CAS No. 448906-60-3 ] {[proInfo.proName]}

Name: 448906-60-3|(4-Bromo-6-methylpyridin-2-yl)methanol|95%
Brand: Ambeed
SKU: A168288
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Quality Control of [ 448906-60-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 448906-60-3 ]

SDS Specification

Alternatived Products of [ 448906-60-3 ]

Product Details of [ 448906-60-3 ]

CAS No. :	448906-60-3	MDL No. :	MFCD07374946
Formula :	C₇H₈BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VSYVUCDSONNKNP-UHFFFAOYSA-N
M.W :	202.05	Pubchem ID :	67027007
Synonyms :

Calculated chemistry of [ 448906-60-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.03
TPSA :	33.12 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) :	-6.76 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.83
Log Po/w (XLOGP3) :	1.09
Log Po/w (WLOGP) :	1.49
Log Po/w (MLOGP) :	0.98
Log Po/w (SILICOS-IT) :	2.31
Consensus Log Po/w :	1.54

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.16
Solubility :	1.41 mg/ml ; 0.00696 mol/l
Class :	Soluble
Log S (Ali) :	-1.38
Solubility :	8.47 mg/ml ; 0.0419 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.1
Solubility :	0.161 mg/ml ; 0.000796 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.69

Safety of [ 448906-60-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 448906-60-3 ]

* 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 [ 448906-60-3 ]
Downstream synthetic route of [ 448906-60-3 ]

[ 448906-60-3 ] Synthesis Path-Upstream 1~5

1
[ 5093-68-5 ]
[ 448906-60-3 ]

Reference： [1] Chemistry - An Asian Journal, 2014, vol. 9, # 7, p. 1808 - 1816

2
[ 22282-99-1 ]
[ 67-56-1 ]
[ 448906-60-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 1, p. 110 - 130
[2] Patent: WO2009/24905, 2009, A1, . Location in patent: Page/Page column 75; 80-81
[3] Patent: US2011/212998, 2011, A1, . Location in patent: Page/Page column 27
[4] Patent: WO2009/109872, 2009, A1, . Location in patent: Page/Page column 29

3
[ 108-48-5 ]
[ 448906-60-3 ]

Reference： [1] Chemistry - An Asian Journal, 2014, vol. 9, # 7, p. 1808 - 1816

4
[ 1073-23-0 ]
[ 448906-60-3 ]

Reference： [1] Chemistry - An Asian Journal, 2014, vol. 9, # 7, p. 1808 - 1816

5
[ 4808-64-4 ]
[ 448906-60-3 ]

Reference： [1] Chemistry - An Asian Journal, 2014, vol. 9, # 7, p. 1808 - 1816

[ 448906-60-3 ] Synthesis Path-Downstream 1~32

1
[ 22282-99-1 ]
[ 67-56-1 ]
[ 448906-60-3 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 4-bromo-2-methyl-pyridine (5.70 g, 32.14 mmol) in methanol (100 ml_), H2SO4 (0.3 ml_) is added. The mixture is heated to reflux before a solution of ammonium peroxydi sulfate (7.33 g, 32.14 mmol) in water (53 ml_) is carefully added. The mixture is stirred at reflux fr 2 h before two more portions of ammonium peroxydisulfate (2x7.33 g) is added as a sat. aq. solution. Stirring is continued at reflux for 3 h. Methanol is removed under reduced pressure and the remaining solution is diluted with sat. aq. NaHCO3 solution and extracted with EA. The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 3:7 to give (4-bromo-6- methyl-pyhdin-2-yl)-methanol (1.31 g) as pale yellow solid; LC-MS: tR = 0.31 min; [M+1]+ = 201.96; 1H NMR (CDCI3): £2.55 (s, 3 H), 3.59 (s br, 1 H), 4.72 (s br, 2 H), 7.28 (s, 2 H); A solution of 4-bromo-2-methyl-pyridine (735 mg, 4.14 mmol) in methanol (80 ml_) and H2SO4 (20 mul_) is heated to reflux. A solution of (NH4J2S2O8 (3.78 g, 16.6 mmol) in water (6.5 mL) is added dropwise to the stirred mixture. Upon completion of the addition, refluxing is continued for 2 h. The mixture is cooled and the reaction is quenched by adding 1 M aq. NaS2O3 solution. The mixture is furhter diluted with sat. aq. NaHCO3 solution and extracted twice with EA (2x300 mL). The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 3:2 to give (4-bromo-6-methyl- <n="82"/>pyridin-2-yl)-methanol (156 mg) as a white solid; LC-MS: tR = 0.32 min, [IVM]+ = 201.93.
		a) To a solution of 4-bromo-2-methyl-pyridine (5.70 g, 32.14 mmol) in methanol (100 mL), H2SO4 (0.3 mL) is added. The mixture is heated to reflux before a solution of ammonium peroxydisulfate (7.33 g, 32.14 mmol) in water (53 mL) is carefully added. The mixture is stirred at reflux fuer 2 h before two more portions of ammonium peroxydisulfate (2*7.33 g) is added as a sat. aq. solution. Stirring is continued at reflux for 3 h. Methanol is removed under reduced pressure and the remaining solution is diluted with sat. aq. NaHCO3 solution and extracted with EA. The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 3:7 to give (4-bromo-6-methyl-pyridin-2-yl)-methanol (1.31 g) as pale yellow solid; LC-MS: tR=0.31 min; [M+1]+=201.96; 1H NMR (CDCl3): delta 2.55 (s, 3H), 3.59 (s br, 1H), 4.72 (s br, 2H), 7.28 (s, 2H).
		To a solution of 4-bromo-2-methyl-pyridine (5.70 g, 32.14 mmol) in methanol (100 mL), H2SO4 (0.3 mL) is added. The mixture is heated to reflux before a solution of ammonium peroxydisulfate (7.33 g, 32.14 mmol) in water (53 mL) is carefully added. The mixture is stirred at reflux for 2 h before two more portions of ammonium peroxydisulfate (2x7.33 g) are added as a sat. aq. solution. Stirring is continued at reflux for 3 h. Methanol is removed under reduced pressure and the remaining solution is diluted with sat. aq. NaHCO3 solution and extracted with EA. The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 3:7 to give (4-bromo- 6-methyl-pyridin-2-yl)-methanol (1.31 g) as pale yellow solid; LC-MS: tR = 0.31 min; [M+1]+ = 201.96; 1H NMR (CDCI3): delta 2.55 (s, 3 H), 3.59 (s br, 1 H), 4.72 (s br, 2 H), 7.28 (s, 2 H).

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 110 - 130
[2]Patent: WO2009/24905,2009,A1 .Location in patent: Page/Page column 75; 80-81
[3]Patent: US2011/212998,2011,A1 .Location in patent: Page/Page column 27
[4]Patent: WO2009/109872,2009,A1 .Location in patent: Page/Page column 29

2
[ 448906-60-3 ]
[ 1122090-59-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate; In acetone; at 20 - 40℃; for 2 - 18h;Product distribution / selectivity;	To a solution of (4-bromo-6-methyl-pyhdin-2-yl)-methanol (1.31 g, 6.48 mmol) in acetone (150 mL), KMnO4 (2.61 g, 16.5 mmol) is added. The mixture is stirred at 400C for 2 h before it is filtered over a sintered glass funnel. The filtrate is evaporated to dryness, the remaining solid is washed with water and dried under HV to give 4-bromo-6-methyl-pyridine-2-carboxylic acid potassium salt (1.91 g) as a white solid; LC-MS: tR = 0.45 min, [M+1]+ = 217.89; To a solution of <strong>[448906-60-3](4-bromo-6-methyl-pyridin-2-yl)-methanol</strong> (3.13 g, 15.5 mmol) in acetone (400 ml_), KMnO4 (6.24 g, 39.5 mmol) is added portionwise. The resulting mixture is stirred at rt for 18 h before it is filtered over a glass-filter. The filter cake is washed with water and acetone and the filtrate is concentrated and dried under HV to give crude 4-bromo-6-methyl-pyhdine-2-carboxylic acid potassium salt (5.03 g) as a white solid; 1H NMR (D2O): £2.47 (s, 3 H), 7.58 (s, 1 H), 7.85 (s, 1 H).
	With potassium permanganate; In acetone; at 40℃; for 2h;Product distribution / selectivity;	b) To a solution of <strong>[448906-60-3](4-bromo-6-methyl-pyridin-2-yl)-methanol</strong> (1.31 g, 6.48 mmol) in acetone (150 mL), KMnO4 (2.61 g, 16.5 mmol) is added. The mixture is stirred at 40 C. for 2 h before it is filtered over a sintered glass funnel. The filtrate is evaporated to dryness, the remaining solid is washed with water and dried under HV to give 4-bromo-6-methyl-pyridine-2-carboxylic acid potassium salt (1.91 g) as a white solid; LC-MS: tR=0.45 min, [M+1]+=217.89.
	With potassium permanganate; In acetone; at 40℃; for 2h;	To a solution of <strong>[448906-60-3](4-bromo-6-methyl-pyridin-2-yl)-methanol</strong> (1.31 g, 6.48 mmol) in acetone (150 mL), KMnO4 (2.61 g, 16.5 mmol) is added. The mixture is stirred at 400C for 2 h before it is filtered over a sintered glass funnel. The filtrate is evaporated to dryness, and the remaining solid is washed with water and dried under HV to give 4-bromo-6-methyl- pyridine-2-carboxylic acid potassium salt (1.91 g) as a white solid; LC-MS: tR = 0.45 min, [M+1]+ = 217.89.

Reference： [1]Patent: WO2009/24905,2009,A1 .Location in patent: Page/Page column 75; 81
[2]Patent: US2011/212998,2011,A1 .Location in patent: Page/Page column 27
[3]Journal of Medicinal Chemistry,2014,vol. 57,p. 110 - 130
[4]Patent: WO2009/109872,2009,A1 .Location in patent: Page/Page column 29

3
[ 448906-60-3 ]
[ 1226800-12-9 ]

Yield	Reaction Conditions	Operation in experiment
30%		Example 66i 4-Bromo-2-(difluoromethyl)-6-methylpyridine (4-Bromo-6-methylpyridin-2-yl)methanol (3 g, 14.85 mmol) was dissolved in chloroform (60 mL) under argon. Manganese(IV) oxide (15.19 g, 148.48 mmol) was added. The resulting mixture was stirred at reflux for 2 hours. The reaction mixture was filtered through celite and the filter was washed with chloroform (20 mL). The filtrate was cooled to 0 C. under argon and diethylaminosulphur trifluoride (3.41 mL, 27.84 mmol) was added. The reaction mixture was stirred over night while the temperature was allowed to reach ambient temperature. The reaction was quenched by addition of saturated aqueous sodium bicarbonate solution and was further diluted with dichloromethane. The organic layer was collected and the water phase was extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried (MgSO4), filtered and carefully concentrated at reduced pressure. Purification by silica gel column chromatography (0 to 20% diethyl ether in pentane) gave 1.00 g (30% yield) of the title compound: 1H NMR (600 MHz, CDCl3) delta ppm 7.62 (s, 1H) 7.46 (s, 1H) 6.57 (t, 1H) 2.58 (s, 3H); MS (EI) m/z 221, 223 [M]+.

Reference： [1]Patent: US2010/125081,2010,A1 .Location in patent: Page/Page column 31

4
[ 448906-60-3 ]
[ 947179-03-5 ]

Reference： [1]Patent: US2011/212998,2011,A1
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 110 - 130

5
[ 448906-60-3 ]
[ 1122091-15-9 ]

Reference： [1]Patent: US2011/212998,2011,A1

6
[ 448906-60-3 ]
[ 1122091-18-2 ]

Reference： [1]Patent: US2011/212998,2011,A1

7
[ 448906-60-3 ]
[ 1122091-13-7 ]

Reference： [1]Patent: US2011/212998,2011,A1

8
[ 108-48-5 ]
[ 448906-60-3 ]