[ CAS No. 36953-41-0 ] {[proInfo.proName]}

Name: 36953-41-0|3-Bromo-4-pyridinol|98%
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Quality Control of [ 36953-41-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 36953-41-0 ]

Product Details of [ 36953-41-0 ]

CAS No. :	36953-41-0	MDL No. :	MFCD01646107
Formula :	C₅H₄BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JWHZKNRXTDYNJO-UHFFFAOYSA-N
M.W :	174.00	Pubchem ID :	599549
Synonyms :

Calculated chemistry of [ 36953-41-0 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.96
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) :	-6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.43
Log Po/w (XLOGP3) :	1.19
Log Po/w (WLOGP) :	1.55
Log Po/w (MLOGP) :	0.58
Log Po/w (SILICOS-IT) :	1.64
Consensus Log Po/w :	1.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.22
Solubility :	1.04 mg/ml ; 0.00598 mol/l
Class :	Soluble
Log S (Ali) :	-1.48
Solubility :	5.74 mg/ml ; 0.033 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.3
Solubility :	0.876 mg/ml ; 0.00504 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.31

Safety of [ 36953-41-0 ]

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 [ 36953-41-0 ]

* 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 [ 36953-41-0 ]
Downstream synthetic route of [ 36953-41-0 ]

[ 36953-41-0 ] Synthesis Path-Upstream 1~7

1
[ 25813-25-6 ]
[ 36953-41-0 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -90℃; Stage #2: With water In tetrahydrofuran; hexanes at -90℃;	Step 36-2.; To a solution of T96-2 (8.0 g, 31.3 mmol) in THF (307 mL) at -90° C. was added slowly a solution of n-BuLi (1.15 M in hexanes, 71 mL). The mixture was stirred for 40 min, then water (10 eq) was added and the mixture warmed to room temperature. The solvent was removed under reduced pressure and the resulting residue purified by flash chromatography (acetone:MeOH, 10:1) to give 3.22 g (60percent) of T 96-3.

Reference： [1] Patent: US2010/93720, 2010, A1, . Location in patent: Page/Page column 58
[2] Synlett, 2003, # 11, p. 1678 - 1682
[3] Patent: WO2012/148808, 2012, A1, . Location in patent: Page/Page column 51

2
[ 13534-98-0 ]
[ 36953-41-0 ]

Yield	Reaction Conditions	Operation in experiment
66.2%	With sulfuric acid; sodium nitrite In water at 0 - 95℃;	Concentrated sulfuric acid (85.0mL) and the 3-bromo-4-aminopyridine (113.0g, 0.65mol) were added successively to the distilled water (550.0mL) at 0°C, and then NaNO₂ (63.1g, 0.91mol) aqueous solution (130.0mL) was added drop-wise to maintain the temperature between 0 and 5°C. After stirring at r. t. for 1h, the reaction mixture was heated at 95°C for a further 0.5h. Upon cooling to below 0°C, the mixture was alkalized to pH 6 with saturated sodium hydroxide solution, washed with ethyl acetate (200mL×3) and brine (200mL), dried over anhydrous Na₂SO₄, filtered and concentrated to yield the title compound 2 as a yellow solid (75.1g, 66.2percent). MS (ESI) m/z: 173.9 [M+H]⁺

Reference： [1] European Journal of Medicinal Chemistry, 2016, vol. 120, p. 37 - 50

3
[ 626-64-2 ]
[ 36953-41-0 ]
[ 25813-25-6 ]

Reference： [1] Synthesis, 2001, # 14, p. 2175 - 2179

4
[ 1124-33-0 ]
[ 36953-41-0 ]

Reference： [1] Yakugaku Zasshi, 1951, vol. 71, p. 591,592[2] Chem.Abstr., 1952, p. 980

5
[ 626-64-2 ]
[ 36953-41-0 ]

Reference： [1] Patent: WO2012/148808, 2012, A1,

6
[ 504-24-5 ]
[ 36953-41-0 ]

Reference： [1] European Journal of Medicinal Chemistry, 2016, vol. 120, p. 37 - 50

7
[ 626-64-2 ]
[ 36953-41-0 ]
[ 25813-25-6 ]

Reference： [1] Synthesis, 2001, # 14, p. 2175 - 2179

[ 36953-41-0 ] Synthesis Path-Downstream 1~64

1
[ 1124-33-0 ]
[ 36953-41-0 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1951,vol. 71,p. 591,592
Chem.Abstr.,1952,p. 980

3
[ 626-64-2 ]
[ 36953-41-0 ]
[ 25813-25-6 ]

Reference： [1]Synthesis,2001,p. 2175 - 2179

4
[ 36953-41-0 ]
[ 637348-83-5 ]

Reference： [1]Synlett,2003,p. 1678 - 1682

5
[ 25813-25-6 ]
[ 36953-41-0 ]

Yield	Reaction Conditions	Operation in experiment
60%		Step 36-2.; To a solution of T96-2 (8.0 g, 31.3 mmol) in THF (307 mL) at -90 C. was added slowly a solution of n-BuLi (1.15 M in hexanes, 71 mL). The mixture was stirred for 40 min, then water (10 eq) was added and the mixture warmed to room temperature. The solvent was removed under reduced pressure and the resulting residue purified by flash chromatography (acetone:MeOH, 10:1) to give 3.22 g (60%) of T 96-3.
		To a stirred solution of 3,5-dibromopyridin-4-ol (IN-11; 2.5 g, 0.00988 mol) in dry tetrahydrofuran (100 mL) at -100 C was added 1.6 M t-butyl lithium in hexane (15.6 mL, 0.0247 mol) drop wise under nitrogen atmosphere and stirred for 2 h at -100 C. The reaction mixture was quenched with water (1.77 g, 0.0988 mol) at -100 C and allows the reaction mixture to RT slowly. The reaction mixture was evaporated. The obtained crude was purified with silica gel chromatography by 0 -12% methanol in dichloromethane to afford the title compound. 1H NMR (400 MHz, DMSO-i¾) delta: 11.71 (s, 1 H), 8.15 (s, 1 H), 7.66-7.65 (d, J= 5.6 Hz, 1 H), 6.20-6.18 (d, J=6.4 Hz, 1 H). MS (M+l): 173.8

Reference： [1]Patent: US2010/93720,2010,A1 .Location in patent: Page/Page column 58
[2]Synlett,2003,p. 1678 - 1682
[3]Patent: WO2012/148808,2012,A1 .Location in patent: Page/Page column 51

6
[ 36953-41-0 ]
[ 910777-72-9 ]
3-(8-([(2,6-dimethylphenyl)methyl]amino)-2,3-dimethylimidazo[1,2-a]pyridin-6-yl)-4(1H)-pyridinone hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 86.; 3-(8-{ [(2,6-Dimethylphenyl)methyl] amino}-2,3-dimethyIimidazo [1 ,2-a] pyridin-6- ne hydrochlorideA mixture of iV-[(2,6-dimethylphenyl)methyl]-2,3-dimethyl-6-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)imidazo[ 1 ,2-alpha]pyridin-8-amine ( ~1.4 mmol; crude product from Description 45) and <strong>[36953-41-0]3-bromo-4-hydroxypyridine</strong> (250 mg, 1.4 mmol) in 2M aqueous sodium carbonate (1.5 mL) and dimethylformamide (3 mL) was degassed with argon and then treated with [I5I'- bis(diphenylphosphino)ferrocene]dichlororhoalladium (10 mg, 0.01 mmol). The mixture was heated in an Initiator Microwave Synthesizer at 1000C for 2 hours. The resulting reaction mixture was applied to an Isolute SCX cartridge. Elution with methanol, then 2M NH3 in methanol gave, after evaporation, the crude product which was purified by MDAP. Combined fractions were applied to an Isolute SCX EPO <DP n="93"/>cartridge. Elution with methanol, then 2M NH3 in methanol gave, after evaporation, the title compound as a free base. The product was dissolved in methanol (3 mL) and then IM HCl in diethyl ether (0.5 mL) was added. After stirring for 5 minutes, the solvents were evaporated to yield the title compound. 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 91-92

7
[ 36953-41-0 ]
[ 100-39-0 ]
[ 1019767-63-5 ]

Yield	Reaction Conditions	Operation in experiment
69%		SYNTHETIC PREPARATION 1; Synthesis of 4-(benzyloxy)-3-bromopyridine To a stirred solution of <strong>[36953-41-0]3-bromo-4-pyridinol</strong> (0.45 g, 2.60 mmol) in N, N- dimethylformamide (20.0 ml_) was added sodium hydride (0.13 g, 3.10 mmol) at 0 0C. The mixture was allowed to stir for 30 min at 0 0C before the slow addition of benzylbromide (0.38 ml_, 3.10 mmol). The mixture was stirred at ambient temperature overnight and quenched with saturated ammonium chloride (50.0 ml_). The mixture <n="108"/>was extracted with ethyl acetate (3 x 30.0 mL). The combined organic layers was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was subjected to column chromatography eluted with 2% methanol in ethyl acetate to give 4-(benzyloxy)-3-bromopyridine (0.48 g, 69%): 1H NMR (300 MHz, CDCI3) delta 7.78 (d, J = 2.3 Hz, 1 H), 7.41-7.34 (m, 4H), 7.21-7.14 (m, 2H), 6.42 (d, J = 7.6 Hz, 1 H), 4.79 (s, 2H); MS (ES+) m/z 264.3 (M + 1 ), 266.3 (M + 1 ).

Reference： [1]Patent: WO2008/46049,2008,A1 .Location in patent: Page/Page column 106-107

8
[ 36953-41-0 ]
[ 122151-36-4 ]
[ 1014986-65-2 ]

Yield	Reaction Conditions	Operation in experiment
42%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃;	Step 36-3.; T 96-3 (3.22 g, 18.4 mmol), PPh3 (4.82 g, 18.4 mmol) and the mono-PMB ether of (R)-glycerol (T96-A, synthesized from the corresponding diol using standard methods, 1.8 g, 9.2 mmol) were dissolved in THF (14 mL). The mixture was cooled to 0 C., then DIAD (3.5 mL, 17.9 mmol) added dropwise maintaining the temperature at 0 C. The solution was stirred at 0 C. for 1 h, then at rt O/N. The mixture was concentrated under reduced pressure and the residue purified by flash chromatography (50/50 EtOAc/Hex) to yield T96-4(R) (42%).

Reference： [1]Patent: US2010/93720,2010,A1 .Location in patent: Page/Page column 58

9
[ 626-64-2 ]
[ 36953-41-0 ]

Reference： [1]Patent: WO2012/148808,2012,A1

10
[ 36953-41-0 ]
[ 76-04-0 ]
[ 1214377-46-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; N,N-dimethyl-formamide; at 120℃; for 0.75h;microwave irradiation;	To a stirred solution of 3-bromopyridin-4-ol (L); 0.5 g, 0.00287 mol) in mixture of N,N-dimethylformamide (10.0 mL), water(l mL), was added 2-chloro-2,2- difluoroacetic acid (0.74 g, .00574 mol) and potassium carbonate (0.47 g, 0.00344 mol). The resulting mixture was heated under microwave irradiation at 120 C for 45 min. The reaction mixture was cooled to room temperature and poured into water (10.0 mL) and extracted with ethyl acetate (2 x 50.0 mL). Combined organic phase was washed with saturated sodium bicarbonate solution, water, saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated under vacuum to afford crude product. The crude was purified by silica gel (60 - 120) column chromatography using 0- 8% methanol in dichloromethane to afford the title compound (IN-13). 1H NMR (400 MHz, DMSO-i/6) delta: 8.606-8.60 (d, J= 2.4 Hz, 1 H), 8.08-8.05 (dd, J=5.2 Hz, 1 H), 7.67- 7.37 (t, J=58.8 Hz, 1 H), 6.38-6.36 (dd, J=7.2 Hz, 1 H). MS (M+l): 223.8.

Reference： [1]Patent: WO2012/148808,2012,A1 .Location in patent: Page/Page column 52

11
[ 36953-41-0 ]
[ 598-32-3 ]
[ 1567216-98-1 ]