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[ CAS No. 917471-30-8 ] {[proInfo.proName]}

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Chemical Structure| 917471-30-8
Chemical Structure| 917471-30-8
Structure of 917471-30-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 917471-30-8 ]

CAS No. :917471-30-8 MDL No. :MFCD18258851
Formula : C8H8BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QICKHKWSOJEAII-UHFFFAOYSA-N
M.W : 160.97 Pubchem ID :57416482
Synonyms :

Calculated chemistry of [ 917471-30-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.8
TPSA : 53.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.51
Log Po/w (WLOGP) : -0.79
Log Po/w (MLOGP) : -0.42
Log Po/w (SILICOS-IT) : -0.47
Consensus Log Po/w : -0.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.46
Solubility : 5.54 mg/ml ; 0.0344 mol/l
Class : Very soluble
Log S (Ali) : -1.2
Solubility : 10.1 mg/ml ; 0.063 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.38
Solubility : 6.79 mg/ml ; 0.0422 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.6

Safety of [ 917471-30-8 ]

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

Application In Synthesis of [ 917471-30-8 ]

* 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 [ 917471-30-8 ]
  • Downstream synthetic route of [ 917471-30-8 ]

[ 917471-30-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 917772-69-1 ]
  • [ 917471-30-8 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane; toluene at -40 - -20℃; for 1.5 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexane; toluene
Method G. Step 2;To A 1000 ml_ flame dried flask charged with anhydrous toluene (1.6 mL/mmol, 188 ml_) and anhydrous THF (0.4 ml_ / mmol47 ml_) under nitrogen was added triisopropyl borate (32 ml_, 141.36 mmol, 1.2 equiv.) and 3-bromo-3- propynylpyridine (23 gm, 117.8 mmol). The mixture was cooled to -40 0C followed by addition of n-Butyllithium (2.5 M in hexanes, 56 ml_, 141.36 mmol) via a syringe pump over 1 hr. The mixture was stirred for an additional 0.5 hr while the temperature was held at -400C before it was warmed to - 200C followed by addition of 2 N aq. HCI (120 ml_). After removal of the organic layer, the pH of the aqueous phase was adjusted to pH7 using a 5 N NaOH solution. A white solid product precipitated as the pH approached 7. The aq. mixture was then saturated with NaCI using solid NaCI, and extracted three times with THF (150 ml_). The combined THF extracts were evaporated in vacuo to provide a solid, (18 gm, 95 percent yield).NMR(H1, CDCI3) for G3: δ 8.67, s, 1 H; 8.48, s, 1 H; 8.09, s, 1 H; 2.06, s, 3H.
87%
Stage #1: With n-butyllithium; Triisopropyl borate In 2-methyltetrahydrofuran; toluene at -50℃; for 1.5 h;
Stage #2: With hydrogenchloride; water In 2-methyltetrahydrofuran; toluene at 20℃; for 0.333333 h;
Stage #3: With sodium hydroxide In 2-methyltetrahydrofuran; water; toluene
Intermediate 155-(Prop-1-ynyl)pyridin-3-ylboronic acid; 3-Bromo-5-(prop-1-ynyl)pyridine (Intermediate 14, 25 g, 117 mmol), 2-methyl-tetrahydrofuran (60 mL), toluene (200 mL) and triisopropyl borate (33.2 mL, 140.78 mmol) were mixed. The mixture was cooled to -50° C. To the cold mixture was added n-BuLi (59.8 mL, 149.5 mmol) dropwise during 30 min. The mixture was stirred for 60 min. at -50° C. 2M HCl aq. (100 mL) was added. The mixture was then allowed to reach r.t. and stirred for 20 min. The organic and water phase were separated. The organic phase was extracted with NaOH (2M aq.) (2.x.100 mL). The water phases were combined and the pH was adjusted to pH 5. The product was extracted with 2-methyl-THF (2.x.100 mL). The organic phase was dried with Na2SO4, filtered and concentrated to give the title compound (16.47 g, 87percent yield): 1H NMR (500 MHz, CD3OD) δ ppm 2.11 (s, 3H) 8.21 (br. s., 1H) 8.53 (m, 2H); MS (APCI+) m/z 162.2 [M+H]+.
87%
Stage #1: With n-butyllithium; Triisopropyl borate In 2-methyltetrahydrofuran; toluene at -50℃; for 1.5 h;
Stage #2: With hydrogenchloride; water In 2-methyltetrahydrofuran; toluene
3-Bromo-5-(prop-l-ynyl)pyridine (Intermediate 24, 25 g, 117 mmol), 2-Me THF (60 mL), toluene (200 mL) and triisopropyl borate (33.2 mL, 140.78 mmol) were mixed. The mixture was cooled to -50 °C. To the cold mixture was added n-BuLi (59.8 mL, 149.5 mmol) dropwise during 30 min. The mixture was stirred for 60 min. at -50 °C. 2M HC1 aq. (100 mL) was added. The mixture was then allowed to reach r.t. and stirred for 20 min. The organic and water phase were separated. The organic phase was extracted with NaOH (2M aq.) (2x100 mL). The water phases were combined and the pH was adjusted to pH 5. The product was extracted with 2- methyl-THF (2x100 mL). The organic phase was dried with Na2SC"4, filtered and concentrated to give the title compound (16.47 g, 87percent yield): 1H MR (500 MHz, CD3OD) δ ppm 2.11 (s, 3 H) 8.21 (br. s., 1 H) 8.53 (m, 2 H); MS (APCI+) m/z 162.2 [M+H]+.
87%
Stage #1: With n-butyllithium; Triisopropyl borate In 2-methyltetrahydrofuran; toluene at -50℃; for 1.5 h;
Stage #2: With hydrogenchloride In 2-methyltetrahydrofuran; water; toluene at -50 - 25℃;
3-Bromo-5-(prop-l-ynyl)pyridine (Intermediate 2, 25 g, 117 mmol), 2-methyl- tetrahydrofuran (60 mL), toluene (200 mL) and triisopropyl borate (33.2 mL, 140.78 mmol) were mixed. The mixture was cooled to -50 °C. To the cold mixture was added n-BuLi (59.8 mL, 149.5 mmol) dropwise during 30 min. The mixture was stirred for 60 min. at -50 °C. 2M HC1 aq. (100 mL) was added. The mixture was then allowed to reach r.t. and stirred for 20 min. The organic andwater phase were separated. The organic phase was extracted with NaOH (2M aq.) (2x100 mL). The water phases were combined and the pH was adjusted to pH 5. The product was extracted with 2- methyl-THF (2x100 mL). The organic phase was dried with Na2S04, filtered and concentrated to give the title compound (16.47 g, 87percent yield): 1H NMR (500 MHz, CD3OD) δ ppm 2.11 (s, 3 H) 8.21 (br. s., 1 H) 8.53 (m, 2 H); MS (APCI+) m/z 162.2 [M+H]+.
62%
Stage #1: With n-butyllithium; Triisopropyl borate In tetrahydrofuran; toluene at -78 - 20℃; for 1.41667 h; Inert atmosphere
Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene at 20℃; for 1 h;
Stage #3: With sodium hydroxide In water
n-Butyllithium (7.17 niL, 17.93 mmol) was added dropwise over 10 min to a solution of 3- bromo-5-(prop-l-ynyl)pyridine (2.93 g, 14.95 mmol) and triisopropyl borate (4.14 mL, 17.93 mmol) in THF (6 mL) and toluene (24 mL) at -78 0C under a nitrogen atmosphere. The resulting mixture was stirred at -78 0C for 45 min. The cooling bath was removed and the mixture was stirred at rt for 30 min before being cooled to -10 0C. Aqueous 2M HCl (15 mL) was added, the cooling bath removed and the mixture was stirred at rt for 1 h. The organics were removed under reduced pressure and the pH of the resulting aqueous residue was adjusted to 7-8 using an aqueous 20percent NaOH solution. The aqueous mixture was diluted with brine (20 mL) and then saturated with solid NaCl and extracted with THF (3 x 25 mL). The combined organics were dried over MgSO4, filtered and concentrated.

Reference: [1] Patent: WO2006/138264, 2006, A2, . Location in patent: Page/Page column 51
[2] Patent: US2012/165347, 2012, A1, . Location in patent: Page/Page column 27
[3] Patent: WO2013/190298, 2013, A1, . Location in patent: Page/Page column 40; 41
[4] Patent: WO2013/190300, 2013, A1, . Location in patent: Page/Page column 27; 28
[5] Patent: WO2011/2407, 2011, A1, . Location in patent: Page/Page column 60
[6] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 7, p. 2444 - 2449
[7] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 11, p. 897 - 902
  • 2
  • [ 917772-69-1 ]
  • [ 5419-55-6 ]
  • [ 917471-30-8 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: With n-butyllithium In 2-methyltetrahydrofuran; toluene at -60℃; for 1.5 h;
Stage #2: With hydrogenchloride; water In 2-methyltetrahydrofuran; toluene at -50 - 25℃; for 0.333333 h;
Stage #3: With sodium hydroxide In 2-methyltetrahydrofuran; water; toluene
Example 28i
5-(Prop-1-ynyl)pyridin-3-yl boronic acid
3-Bromo-5-(prop-1-ynyl)pyridine (25 g, 117 mmol, Example 27i), 2-methyl-tetrahydrofuran (60 mL), toluene (200 mL) and triisopropyl borate (33.2 mL, 140 mmol) were mixed.
The mixture was cooled to -50° C.
To the cold mixture was added n-BuLi (59.8 mL, 149.5 mmol) dropwise during 30 minutes.
The mixture was stirred for 60 minutes at -50° C. 2M HCl aq. (100 mL) was added.
The mixture was then allowed to reach r.t. and stirred for 20 minutes.
The organic and water phase were separated.
The organic phase was extracted with NaOH (2M aq.) (2*100 mL).
The water phases were combined and pH adjusted to pH 5.
The product was extracted with 2-methyl THF (2*100 mL).
The organic phase was dried with sodium sulphate, filtered and concentrated to give the title compound (16.47 g, 87percent yield): 1H NMR (500 MHz, CD3OD) δ ppm 2.11 (s, 3H), 8.21 (br. s., 1H), 8.53 (m, 2H); MS (APCI+) m/z 162.2 [M+H]+.
62%
Stage #1: With n-butyllithium In tetrahydrofuran; toluene at -78 - -10℃; Inert atmosphere
Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene at 20℃; for 1 h;
Stage #3: With sodium hydroxide In tetrahydrofuran; water; toluene
Example 26i
5-(Prop-1-ynyl)pyridin-3-yl boronic acid
n-Butyllithium (7.17 mL, 17.93 mmol) was added dropwise over 10 min to a solution of 3-bromo-5-(prop-1-ynyl)pyridine (2.93 g, 14.95 mmol) and triisopropyl borate (4.14 mL, 17.93 mmol) in THF (6 mL) and toluene (24 mL) at -78 0C under a nitrogen atmosphere. The resulting mixture was stirred at -78 °C for 45 min. The cooling bath was removed and the mixture was stirred at rt for 30 min before being cooled to -10 0C. Aqueous 2M HCl (15 mL) was added, the cooling bath removed and the mixture was stirred at rt for 1 h. The organics were removed under reduced pressure and the pH of the resulting aqueous residue was adjusted to 7-8 using an aqueous 20percent NaOH solution. The aqueous mixture was diluted with brine (20 mL) and then saturated with solid NaCl and extracted with THF (3 x 25 mL). The combined organics were dried over MgSO4, filtered and concentrated.Recrystallization from MeOH gave 1.5 g (62percent yield) of the title compound: MS (ES-) m/z 160 [M-I]-.
Reference: [1] Patent: US2012/165346, 2012, A1, . Location in patent: Page/Page column 19
[2] Patent: WO2011/2408, 2011, A1, . Location in patent: Page/Page column 55-56
[3] Patent: WO2012/162334, 2012, A1, . Location in patent: Page/Page column 34-35
[4] Patent: WO2014/98831, 2014, A1, . Location in patent: Page/Page column 32; 33
  • 3
  • [ 625-92-3 ]
  • [ 917471-30-8 ]
Reference: [1] Patent: WO2011/2407, 2011, A1,
[2] Patent: WO2011/2408, 2011, A1,
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 7, p. 2444 - 2449
[4] Patent: US2012/165346, 2012, A1,
[5] Patent: US2012/165347, 2012, A1,
[6] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 11, p. 897 - 902
[7] Patent: WO2012/162334, 2012, A1,
[8] Patent: WO2013/190298, 2013, A1,
[9] Patent: WO2013/190300, 2013, A1,
[10] Patent: WO2014/98831, 2014, A1,
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