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[ CAS No. 6602-33-1 ] {[proInfo.proName]}

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Chemical Structure| 6602-33-1
Chemical Structure| 6602-33-1
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Product Details of [ 6602-33-1 ]

CAS No. :6602-33-1 MDL No. :MFCD01318479
Formula : C5H3Br2NO Boiling Point : -
Linear Structure Formula :- InChI Key :RKOLKIWJSXSHLV-UHFFFAOYSA-N
M.W : 252.89 Pubchem ID :81077
Synonyms :

Calculated chemistry of [ 6602-33-1 ]

Physicochemical Properties

Num. heavy atoms : 9
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 : 41.66
TPSA : 33.12 Ų

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) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.55
Log Po/w (XLOGP3) : 2.55
Log Po/w (WLOGP) : 2.31
Log Po/w (MLOGP) : 1.36
Log Po/w (SILICOS-IT) : 2.3
Consensus Log Po/w : 2.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.51
Solubility : 0.0786 mg/ml ; 0.000311 mol/l
Class : Soluble
Log S (Ali) : -2.89
Solubility : 0.324 mg/ml ; 0.00128 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.16
Solubility : 0.175 mg/ml ; 0.000693 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.8

Safety of [ 6602-33-1 ]

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

Application In Synthesis of [ 6602-33-1 ]

* 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 [ 6602-33-1 ]
  • Downstream synthetic route of [ 6602-33-1 ]

[ 6602-33-1 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 109-00-2 ]
  • [ 6602-32-0 ]
  • [ 6602-33-1 ]
YieldReaction ConditionsOperation in experiment
29% With bromine In sodium hydroxide; water; ethyl acetate EXAMPLE 7
N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-2-carboxamide Dihydrochloride
Preparation of the Acid:
Bromine (52 mL, 1.0 mole) is added drop-wise to a solution of NaOH (93 g, 2.32 mole) in 800 mL water in an ice bath.
The resulting bromate solution is added drop-wise to a solution of 3-pyridinol (47.6 g, 0.5 mole) in 125 mL water containing NaOH (20 g, 0.5 mole) in a flask that is in an ice bath, and the reaction is stirred 1.5 h at 0-5° C.
The pH is adjusted to 3 with 12N HCl, and the solid precipitate is collected, washed with water, and dried.
The crude solid is dissolved in 400 mL EtOAc, and the solution is diluted with 1600 mL heptane, and is allowed to crystallize overnight.
The solid is collected to give 2-bromo-3-pyridinol (C29).
The mother liquor is concentrated in vacuo to a pale yellow solid.
The crude solid is recrystallized from 1:1 EtOH/water to afford 2,6-dibromo-3-pyridinol (C28) (29percent yield). HRMS (FAB) calculated for C5H3Br2NO+H: 251.8661, found 251.8669 (M+H)+.
20%
Stage #1: With bromine; sodium hydroxide In water at 0℃; for 1.5 h;
Stage #2: With hydrogenchloride In water
Stage #3: for 72 h;
[0594] Preparation of 71 [0595] Prepared according to the method of Wishka et al, WO 2002/100857. [0596] Bromine (21.6 mL, 421 mmol) was added dropwise to a stirred solution of sodium hydroxide (39.2 g, 976 mmol)) in water (800 mL) at 0° C. The resultant bromate solution was then added dropwise to a stirred solution of 3-hydroxypyridine (20.0 g, 210 mmol), and sodium hydroxide (8.4 g, 34.3 mmol) in water (50 mL) at 0° C. The reaction mixture was stirred at 0° C. for 90 minutes, acidified to pH 2 by addition of 12M HCl soln., and the resultant precipitate collected, washed with water and dried on the filter. The solid was dissolved in EtOAc (170 mL), the solution diluted with heptane (620 mL) and allowed to crystallise for 3 days. The solid was collected, to give 2-bromopyridin-3-ol, and the mother liquor concentrated in vacuo to give a pale yellow solid. The crude solid was recrystallised from EtOH/water and dried in vacuo to afford 71 as a pale yellow crystalline solid (10.8 g, 42.7 mmol, 20percent).
Reference: [1] Patent: US2003/45540, 2003, A1,
[2] Patent: US2013/53372, 2013, A1, . Location in patent: Paragraph 0594; 0595; 0596
  • 2
  • [ 109-00-2 ]
  • [ 6602-32-0 ]
  • [ 6602-33-1 ]
  • [ 6602-34-2 ]
Reference: [1] Synthesis, 2001, # 14, p. 2175 - 2179
  • 3
  • [ 109-00-2 ]
  • [ 6602-32-0 ]
  • [ 6602-33-1 ]
  • [ 129611-31-0 ]
Reference: [1] Synthesis, 1990, # 6, p. 497 - 498
[2] Chemistry - A European Journal, 2010, vol. 16, # 28, p. 8439 - 8445
[3] Synthesis, 1990, # 6, p. 497 - 498
  • 4
  • [ 109-00-2 ]
  • [ 6602-33-1 ]
YieldReaction ConditionsOperation in experiment
46% at 0 - 20℃; for 5 h; 5.40
2,6-Dibromopyridin-3-ol (30)
An ice-cold solution of bromine (16.2 mL, 315 mmol) in sodium hydroxide (2.5 M, 320 mL, 800 mmol) was added dropwise to a stirred solution of pyridin-3-ol (10.0 g, 105 mmol) in sodium hydroxide (2.5 M, 110 mL, 275 mmol).
The solution was stirred at 0 °C for 1 h and then at room temp for 4 h.
A small amount of precipitate that formed was removed by filtration.
The filtrate was cooled, and concentrated hydrochloric acid was added until the pH reached 1.
The solid was collected by filtration, washed with water, dried, and recrystallised from carbon tetrachloride to give 30 (12.1 g, 46percent) as a beige coloured solid: 1H NMR (400 MHz, DMSO-d6) δ = 11.14 (br s, 1H), 7.47 (d, J = 8.0 Hz, 1H), 7.26 (d, J = 8.0 Hz, 1H); MS ES-ve m/z 250, 252, 254 (M-H)-.
43.9%
Stage #1: With bromine; sodium hydroxide In water at 0 - 20℃;
Stage #2: With hydrogenchloride In water
Step 1. Synthesis of 2,6-dibromopyridin-3-ol (39): 38 39 To a 10percent aqueous NaOH solution (300ml) was added bromine (48.6 ml, 946 mmol) at O C. An ice cooled solution of pyridin-3-ol (38; 30 g, 315 mmol) in 10ml 10percent NaOH solution was then added slowly. The reaction mixture was stirred for 15 min at 0 C and 45 min at room temperature. The resulting precipitate was filtered and the filtrate was acidified with aqueous HCl (pH = 4) upon which the crude product precipitated out. The resulting precipitate was filtered and purified by chromatography (EtO Ac/petroleum ether = 1 :20) to give the target compound 39(3Og, 43.9percent yield). MS (ESI) calcd for C5H3Br2NO 251.86, found 251.85 [M+H].
37%
Stage #1: at 0 - 20℃; for 2.5 h;
Stage #2: at 70℃; for 24 h;
A solution (cooled to 0 °C) of bromine (8.1 mL, 158 mmol) in 2 N NaOH (160 mL) was added over 30 min to a solution of pyridin-3-ol (34a; 5.0 g, 53 mmol; Sigma-Aldrich, St. Louis, MO) in 2 N NaOH (55 mL) at 0 °C. The resulting mixture was stirred at 0 °C for 30 min, then allowed to stand for 2 h at ambient temperature. The reaction mixture was vacuum filtered, and the filtrate was adjusted to pH ~ 1 by adding conc. HCl to the a stirred filtrate at 0 °C. The resulting precipitate was collected by vacuum filtration, rinsed with water, and dried in vacuo to give an off-white solid (8 g). This material was dissolved in CCl4(200 mL) at 70 °C, and the resulting solution was slowly cooled to ambient temperature and allowed to stand for 24 h. CCl4was decanted, and the solid was triturated with small portions of CCl4(2×), providing crystalline material which was collected by vacuum filtration and dried in vacuo to provide 2,6-dibromopyridin-3-ol (4.9 g, 19 mmol, 37percent yield) as off-white crystals.
36% With bromine; sodium hydroxide In water at 0 - 20℃; for 18 h; Step a: 2,6-dibromopyridin-3-ol To a 3N aqueous NaOH solution (790 ml) was added bromine (40.7 ml, 0.789 mol) at 0 °C. An ice cooled solution of pyridine-3-ol (25 g, 0.263 mol) in 150 ml 10 percent NaOH solution was then added slowly and the mixture was stirred at ambient temperature for 18 hours, filtered and the filtrate was acidified with cone. HCI to pH 2. The precipitate was filtered off, washed with H20, and dissolved in Ethyl acetate (300 mL). The solution was dried over MgS04 and concentrated in vacuo. Purification by silica column flash chromatography (petroleum / Ethyl acetate, 3/1 ) to give the title product as an off white solid (23.6 g, 36 percent). 1H NMR (400Mz, DMSO-d6): δ: 7.23 (d, J=7.5, 1 H); 7.45 (d, J=9, 1 H); δ 1 1 .13 (s, 1 H),
20%
Stage #1: With bromine; sodium hydroxide In water at 0℃;
Stage #2: With hydrogenchloride In water
Preparation of 7lPrepared according to the method of Wishka et al, WO 2002/100857.Bromine (21.6 mL, 421 mmol) was added dropwise to a stirred solution of sodium hydroxide (39.2 g, 976 mmol)) in water (800 mL) at 0 °C. The resultant bromate solution was then added dropwise to a stirred solution of 3-hydroxypyridine (20.0 g, 210 mmol), and sodium hydroxide (8.4 g, 34.3 mmol) in water (50 mL) at 0 °C. The reaction mixture was stirred at 0 °C for 90 minutes, acidified to pH 2 by addition of 12M HCl soln., and the resultant precipitate collected, washed with water and dried on the filter. The solid was dissolved in EtOAc (170 mL), the solution diluted with heptane (620 mL) and allowed to crystallise for 3 days. The solid was collected, to give 2-bromopyridin-3-ol, and the mother liquor concentrated in vacuo to give a pale yellow solid. The crude solid was recrystallised from EtOH/water and dried in vacuo to afford 71 as a pale yellow crystalline solid (10.8 g, 42.7 mmol, 20percent).

Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 15, p. 4298 - 4311
[2] Australian Journal of Chemistry, 1981, vol. 34, # 4, p. 927 - 932
[3] Patent: WO2010/56549, 2010, A1, . Location in patent: Page/Page column 97
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 24, p. 5630 - 5634
[5] Patent: WO2013/181931, 2013, A1, . Location in patent: Page/Page column 40
[6] Patent: WO2011/98776, 2011, A1, . Location in patent: Page/Page column 61
[7] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 1281,1286
[8] Patent: EP2017277, 2009, A1, . Location in patent: Page/Page column 30
[9] Patent: WO2014/29684, 2014, A1, . Location in patent: Page/Page column 45; 46
[10] Patent: EP3255042, 2017, A2, . Location in patent: Paragraph 0088; 0089
[11] Angewandte Chemie - International Edition, 2018, vol. 57, # 18, p. 5100 - 5104[12] Angew. Chem., 2018, vol. 130, # 18, p. 5194 - 5198,5
  • 5
  • [ 109-00-2 ]
  • [ 6602-32-0 ]
  • [ 6602-33-1 ]
YieldReaction ConditionsOperation in experiment
29% With bromine In sodium hydroxide; water; ethyl acetate EXAMPLE 7
N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-2-carboxamide Dihydrochloride
Preparation of the Acid:
Bromine (52 mL, 1.0 mole) is added drop-wise to a solution of NaOH (93 g, 2.32 mole) in 800 mL water in an ice bath.
The resulting bromate solution is added drop-wise to a solution of 3-pyridinol (47.6 g, 0.5 mole) in 125 mL water containing NaOH (20 g, 0.5 mole) in a flask that is in an ice bath, and the reaction is stirred 1.5 h at 0-5° C.
The pH is adjusted to 3 with 12N HCl, and the solid precipitate is collected, washed with water, and dried.
The crude solid is dissolved in 400 mL EtOAc, and the solution is diluted with 1600 mL heptane, and is allowed to crystallize overnight.
The solid is collected to give 2-bromo-3-pyridinol (C29).
The mother liquor is concentrated in vacuo to a pale yellow solid.
The crude solid is recrystallized from 1:1 EtOH/water to afford 2,6-dibromo-3-pyridinol (C28) (29percent yield). HRMS (FAB) calculated for C5H3Br2NO+H: 251.8661, found 251.8669 (M+H)+.
20%
Stage #1: With bromine; sodium hydroxide In water at 0℃; for 1.5 h;
Stage #2: With hydrogenchloride In water
Stage #3: for 72 h;
[0594] Preparation of 71 [0595] Prepared according to the method of Wishka et al, WO 2002/100857. [0596] Bromine (21.6 mL, 421 mmol) was added dropwise to a stirred solution of sodium hydroxide (39.2 g, 976 mmol)) in water (800 mL) at 0° C. The resultant bromate solution was then added dropwise to a stirred solution of 3-hydroxypyridine (20.0 g, 210 mmol), and sodium hydroxide (8.4 g, 34.3 mmol) in water (50 mL) at 0° C. The reaction mixture was stirred at 0° C. for 90 minutes, acidified to pH 2 by addition of 12M HCl soln., and the resultant precipitate collected, washed with water and dried on the filter. The solid was dissolved in EtOAc (170 mL), the solution diluted with heptane (620 mL) and allowed to crystallise for 3 days. The solid was collected, to give 2-bromopyridin-3-ol, and the mother liquor concentrated in vacuo to give a pale yellow solid. The crude solid was recrystallised from EtOH/water and dried in vacuo to afford 71 as a pale yellow crystalline solid (10.8 g, 42.7 mmol, 20percent).
Reference: [1] Patent: US2003/45540, 2003, A1,
[2] Patent: US2013/53372, 2013, A1, . Location in patent: Paragraph 0594; 0595; 0596
  • 6
  • [ 109-00-2 ]
  • [ 6602-33-1 ]
  • [ 129611-31-0 ]
Reference: [1] Synthesis, 1990, # 6, p. 497 - 498
[2] Patent: WO2005/21529, 2005, A1, . Location in patent: Page/Page column 32
  • 7
  • [ 109-00-2 ]
  • [ 6602-33-1 ]
  • [ 6602-34-2 ]
Reference: [1] Synthesis, 2001, # 14, p. 2175 - 2179
  • 8
  • [ 109-00-2 ]
  • [ 6602-32-0 ]
  • [ 6602-33-1 ]
  • [ 6602-34-2 ]
Reference: [1] Synthesis, 2001, # 14, p. 2175 - 2179
  • 9
  • [ 109-00-2 ]
  • [ 6602-32-0 ]
  • [ 6602-33-1 ]
  • [ 129611-31-0 ]
Reference: [1] Synthesis, 1990, # 6, p. 497 - 498
[2] Chemistry - A European Journal, 2010, vol. 16, # 28, p. 8439 - 8445
[3] Synthesis, 1990, # 6, p. 497 - 498
  • 10
  • [ 137347-01-4 ]
  • [ 6602-33-1 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 1281,1286
  • 11
  • [ 110-86-1 ]
  • [ 109-00-2 ]
  • [ 7726-95-6 ]
  • [ 6602-33-1 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 1281,1286
  • 12
  • [ 6602-33-1 ]
  • [ 64436-92-6 ]
Reference: [1] Australian Journal of Chemistry, 1981, vol. 34, # 4, p. 927 - 932
  • 13
  • [ 6602-33-1 ]
  • [ 79491-46-6 ]
Reference: [1] Australian Journal of Chemistry, 1981, vol. 34, # 4, p. 927 - 932
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 15, p. 4298 - 4311
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 24, p. 5630 - 5634
  • 14
  • [ 6602-33-1 ]
  • [ 74-88-4 ]
  • [ 79491-45-5 ]
YieldReaction ConditionsOperation in experiment
80% With potassium carbonate In dimethyl sulfoxide for 2 h; Reflux 5.41
2,6-Dibromo-3-methoxypyridine (31)
A suspension of 2,6-dibromopyridin-3-ol (12 g, 47 mmol), potassium carbonate (6.0 g, 43 mmol), methyl iodide (10.1 mL, 162 mmol) and DMSO (20 mL) was refluxed for 2 h.
The reaction mixture was poured into water (60 mL) and was warmed gently at 50 °C with stirring for 30 min.
The reaction mixture was cooled to room temperature and the precipitated solid was collected by filtration, and dried under vacuum.
The residue was crystallised from cyclohexane to give 31 (10.1 g, 80percent) as a pale orange solid: 1H NMR (400 MHz, DMSO-d6) δ = 7.66 (d, J = 8.0 Hz, 1H), 7.52 (d, J = 8.0 Hz, 1H), 3.90 (s, 3H); MS ES+ve m/z 266, 268, 270 (M+H)+.
65% With potassium carbonate In dimethyl sulfoxide at 70℃; for 1.5 h; Sealed tube A mixture of 2,6-dibromopyridin-3-ol (4.9 g, 19 mmol), potassium carbonate (2.4 g, 17 mmol), and iodomethane (4.1 mL, 66 mmol) in DMSO (8 mL) was heated at 70 °C for 1.5 h in a sealed tube. The reaction mixture was then cooled to ambient temperature and poured into water. Excess methyl iodide was removed in vacuo, and the resulting mixture was extracted with DCM (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting orange solid was recrystallized from hot MeOH (20 mL), and the collected crystals were sequentially triturated with MeOH (2×) and hexanes, then dried in vacuo to give brown crystals (1.7 g). The mother liquor was subsequently concentrated in vacuo and chromatographically purified (silica gel, 0–30percent EtOAc/hexanes) to afford additional product (1.66 g), which was combined with the crystalline material to provide 2,6-dibromo-3-methoxypyridine (3.36 g, 13 mmol, 65percent yield).
19% With potassium carbonate In acetone for 3 h; Reflux [0089] Bromine (1.62 mL, 63.09 mmole) was slowly added dropwise to 25 mL of 20 percent sodium hydroxide (NaOH)aqueous solution at 0°C and the mixture was stirred at 0 °C for 15 min. Then, 3-hydroxypyridine (I) (2.0 g, 21.03 mmole)dissolved in 20 percent sodium hydroxide (NaOH) aqueous solution was slowly added dropwise thereto at 0 °C, and themixture was stirred at 0 °C for 2 hours and then at room temperature for 12 hours. The mixture was filtered to removefloating matter and to the resulting solution was slowly added dropwise 2N hydrochloric acid (HCl) to adjust pH to 1∼2.The resulting solid was filtered and dried to provide a white solid. The solid was dissolved in 60 ml of acetone andpotassium carbonate (K2CO3) (2.64 g, 19.13 mmol) and methaneiodide (CH3I) (893.03 mL, 14.34 mmole) were addeddropwise thereto and the solution was stirred with reflux for 3 hrs. The resulting solution was evaporated under reducedpressure to concentrate, diluted with ethylacetate (EA), and washed with water. The washed organic solvent was driedover anhydrous magnesium sulfate (MgSO4), filtered, and then evaporated under reduced pressure to concentrate. Theresulting residue was isolated and purified by silica gel column chromatography (n-Hex/EA = 5/1) to give the title compound(1.04 g, 19 percent).1H NMR (400 MHz, CDCl3) δ 7.38 (d, J = 8.4 Hz, 1H), 7.04 (d, J = 8.0 Hz, 1H), 3.91 (s, 3H).
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 15, p. 4298 - 4311
[2] Australian Journal of Chemistry, 1981, vol. 34, # 4, p. 927 - 932
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 24, p. 5630 - 5634
[4] Patent: EP3255042, 2017, A2, . Location in patent: Paragraph 0088; 0089
[5] Patent: EP2017277, 2009, A1, . Location in patent: Page/Page column 30
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