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[ CAS No. 132308-19-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 132308-19-1
Chemical Structure| 132308-19-1
Chemical Structure| 132308-19-1
Structure of 132308-19-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 132308-19-1 ]

CAS No. :132308-19-1 MDL No. :MFCD09702466
Formula : C7H6ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QHFFLLBWCXVJGO-UHFFFAOYSA-N
M.W : 171.58 Pubchem ID :11298216
Synonyms :

Calculated chemistry of [ 132308-19-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.53
TPSA : 39.19 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) : -5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 2.12
Log Po/w (WLOGP) : 1.52
Log Po/w (MLOGP) : 0.93
Log Po/w (SILICOS-IT) : 1.83
Consensus Log Po/w : 1.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.51
Solubility : 0.529 mg/ml ; 0.00308 mol/l
Class : Soluble
Log S (Ali) : -2.57
Solubility : 0.457 mg/ml ; 0.00267 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.71
Solubility : 0.333 mg/ml ; 0.00194 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 132308-19-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 132308-19-1 ]

* 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 [ 132308-19-1 ]
  • Downstream synthetic route of [ 132308-19-1 ]

[ 132308-19-1 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 40473-01-6 ]
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 132308-19-1 ]
YieldReaction ConditionsOperation in experiment
93% at 50℃; for 24 h; To a solution of 2-bromo-5-chloropyridine (30.0 g, 155.9 mmol) in MeOH (280 mL) was added Pd(OAc)2 (3.5 g, 10.8 mmol), dppf (17.3 g, 37.96 mmol), Et3N (42.0 mL, 312 mmol). The resulting mixture was stirred at 500C under a CO atmosphere (15 psi) for 24 h, then concentrated under reduced pressure to give crude residue. This residue was partitioned between EtOAc (3 X 500 mL) and water (300 mL). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel, by using 10:1 petroleum ether/EtOAc, afforded the title compound as a pale yellow solid (25 g, 93percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.60 (d, J = 1.60 Hz, 1 H), 8.01 (d, J = 8.40 Hz, 1 H), 7.75 (dd, J = 8.40, 2.40 Hz, 1 H), 3.92 (s, 3 H).
93% at 50℃; for 24 h; Intermediate 1 : methyl δ-chloro^-pyridinecarboxylate To a solution of 2-bromo-5-chloropyridine (30.0 g, 155.9 mmol) in MeOH (280 ml.) was added Pd(OAc)2 (3.5 g, 10.8 mmol), dppf (17.3 g, 37.96 mmol), Et3N (42.0 ml_, 312 mmol). The resulting mixture was stirred at 500C under a CO atmosphere (15 psi) for 24 h, then concentrated under reduced pressure to give crude residue. This residue was partitioned between EtOAc (3 X 500 ml.) and water (300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel, by using 10:1 petroleum ether/EtOAc, afforded the title compound as a pale yellow solid (25 g, 93percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.60 (d, J = 1.60 Hz, 1 H), 8.01 (d, J = 8.40 Hz, 1 H), 7.75 (dd, J = 8.40, 2.40 Hz, 1 H), 3.92 (s, 3H).
93% at 50℃; for 24 h; Intermediate 1 : methyl δ-chloro^-pyridinecarboxylate To a solution of 2-bromo-5-chloropyridine (30.0 g, 155.9 mmol) in MeOH (280 ml.) was added Pd(OAc)2 (3.5 g, 10.8 mmol), dppf (17.3 g, 37.96 mmol), Et3N (42.0 ml_, 312 mmol). The resulting mixture was stirred at 500C under a CO atmosphere (15 psi) for 24 h, then concentrated under reduced pressure to give crude residue. This residue was partitioned between EtOAc (3 X 500 ml.) and water (300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel, by using 10:1 petroleum ether/EtOAc, afforded the title compound as a pale yellow solid (25 g, 93percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.60 (d, J = 1.60 Hz, 1 H), 8.01 (d, J = 8.40 Hz, 1 H), 7.75 (dd, J = 8.40, 2.40 Hz, 1 H), 3.92 (s, 3H).
93% at 50℃; for 24 h; Intermediate 1 : methyl δ-chloro^-pyridinecarboxylate To a solution of 2-bromo-5-chloropyridine (30.0 g, 155.9 mmol) in MeOH (280 ml.) was added Pd(OAc)2 (3.5 g, 10.8 mmol), dppf (17.3 g, 37.96 mmol), Et3N (42.0 ml_, 312 mmol). The resulting mixture was stirred at 500C under a CO atmosphere (15 psi) for 24 h, then concentrated under reduced pressure to give crude residue. This residue was partitioned between EtOAc (3 X 500 ml.) and water (300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel, by using 10:1 petroleum ether/EtOAc, afforded the title compound as a pale yellow solid (25 g, 93percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.60 (d, J = 1.60 Hz, 1 H), 8.01 (d, J = 8.40 Hz, 1 H), 7.75 (dd, J = 8.40, 2.40 Hz, 1 H), 3.92 (s, 3H).
93% at 50℃; for 24 h; Intermediate 1 : methyl δ-chloro^-pyridinecarboxylateTo a solution of 2-bromo-5-chloropyridine (30.0 g, 155.9 mmol) in MeOH (280 ml.) was added Pd(OAc)2 (3.5 g, 10.8 mmol), dppf (17.3 g, 37.96 mmol), Et3N (42.0 ml_, 312 mmol). The resulting mixture was stirred at 500C under a CO atmosphere (15 psi) for 24 h, then concentrated under reduced pressure to give crude residue. This residue was partitioned between EtOAc (3 X 500 ml.) and water (300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel, by using 10:1 petroleum ether/EtOAc, afforded the title compound as a pale yellow solid (25 g, 93percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.60 (d, J = 1.60 Hz, 1 H), 8.01 (d, J = 8.40 Hz, 1 H), 7.75 (dd, J = 8.40, 2.40 Hz, 1 H), 3.92 (s, 3H).
93% at 50℃; for 24 h; I. methyl 5-chloro-2-pyridinecarboxylate To a solution of 2-bromo-5-chloropyridine (30.0 g, 155.9 mmol) in MeOH (280 mL) was added Pd(OAc)2 (3.5 g, 10.8 mmol), dppf (17.3 g, 37.96 mmol), Et3N (42.0 mL, 312 mmol). The resulting mixture was stirred at 50°C under a CO atmosphere (15 psi) for 24 h, then concentrated under reduced pressure to give crude residue. This residue was partitioned between EtOAc (3 X 500 mL) and water (300 mL). The combined organic layers were dried (Na2SC>4) and evaporated. Flash chromatography of the residue over silica gel, by using 10: 1 petroleum ether/EtOAc, afforded the title compound as a pale yellow solid (25 g, 93percent yield): 1H NMR (400 MHz, CDC13) δ ppm 8.60 (d, J = 1.60 Hz, 1H), 8.01 (d, J= 8.40 Ηζ,ΙΗ), 7.75 (dd, J = 8.40, 2.40 Hz, 1H), 3.92 (s, 3H).

Reference: [1] Patent: WO2009/76387, 2009, A1, . Location in patent: Page/Page column 26
[2] Patent: WO2010/141538, 2010, A1, . Location in patent: Page/Page column 18
[3] Patent: WO2010/141539, 2010, A1, . Location in patent: Page/Page column 18
[4] Patent: WO2010/141545, 2010, A1, . Location in patent: Page/Page column 19
[5] Patent: WO2010/141540, 2010, A1, . Location in patent: Page/Page column 17
[6] Patent: WO2013/166621, 2013, A1, . Location in patent: Page/Page column 47
  • 2
  • [ 67-56-1 ]
  • [ 128073-03-0 ]
  • [ 132308-19-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[2] Patent: WO2012/88469, 2012, A1, . Location in patent: Page/Page column 152-153
  • 3
  • [ 89809-64-3 ]
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Reference: [1] Patent: US2007/4772, 2007, A1, . Location in patent: Page/Page column 83
  • 4
  • [ 67-56-1 ]
  • [ 89809-64-3 ]
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Reference: [1] Patent: US2006/287341, 2006, A1, . Location in patent: Page/Page column 47
  • 5
  • [ 16110-09-1 ]
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
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Reference: [1] Tetrahedron, 2005, vol. 61, # 26, p. 6330 - 6336
  • 6
  • [ 16110-09-1 ]
  • [ 132308-19-1 ]
Reference: [1] Patent: US5380861, 1995, A,
  • 7
  • [ 16110-09-1 ]
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 132308-19-1 ]
  • [ 881-86-7 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 19, p. 3719 - 3722
  • 8
  • [ 86873-60-1 ]
  • [ 132308-19-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[3] Patent: WO2012/88469, 2012, A1,
  • 9
  • [ 21684-59-3 ]
  • [ 132308-19-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[3] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[4] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
  • 10
  • [ 80287-53-2 ]
  • [ 132308-19-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
  • 11
  • [ 72093-07-3 ]
  • [ 132308-19-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
  • 12
  • [ 6960-22-1 ]
  • [ 132308-19-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
  • 13
  • [ 197079-25-7 ]
  • [ 132308-19-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
  • 14
  • [ 64038-04-6 ]
  • [ 132308-19-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
  • 15
  • [ 247077-42-5 ]
  • [ 132308-19-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
  • 16
  • [ 1199-48-0 ]
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
  • 17
  • [ 70788-54-4 ]
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
  • 18
  • [ 858844-85-6 ]
  • [ 132308-19-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
  • 19
  • [ 186581-53-3 ]
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Reference: [1] Bioscience, Biotechnology, and Biochemistry, 1994, vol. 58, # 11, p. 2054 - 2056
  • 20
  • [ 16110-09-1 ]
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
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  • [ 881-86-7 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 19, p. 3719 - 3722
  • 21
  • [ 132308-19-1 ]
  • [ 209526-98-7 ]
YieldReaction ConditionsOperation in experiment
99% at 0 - 20℃; for 2.5 h; To a cooled (00C) solution of methyl δ-chloro^-pyridinecarboxylate (43 g, 251 mmol) in methanol (400 ml_) was added NaBH4 (28.7 g, 754 mmol) in small portions over approximately 30 min. After addition, the reaction mixture was stirred at room temperature for 2 h, at which time TLC analysis showed the completion of the reaction. The reaction mixture was then concentrated under reduced pressure, and the residue was adjusted to pH 1 by adding 1 N HCI. The resulting solution was extracted with EtOAc (3 X 300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel using 10:1 petroleum ether/EtOAc as eluent provided the title compound (36 g, 99percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.44 (d, J = 1 .60 Hz, 1 H), 7.62 (dd, J = 8.40, 2.40 Hz, 1 H), 7.25 (d, J = 8.40 Hz, 1 H), 4.69 (s, 2 H), 3.83 (s, 1 H).
99% at 0 - 20℃; for 2.5 h; Intermediate 2: (5-chloro-2-pyridinyl)methanol To a cooled (00C) solution of methyl 5-chloro-2-pyridinecarboxylate (43 g, 251 mmol) in methanol (400 ml.) was added NaBH4 (28.7 g, 754 mmol) in small portions over approximately 30 min. After addition, the reaction mixture was stirred at room temperature for 2 h, at which time TLC analysis showed the completion of the reaction. The reaction mixture was then concentrated under reduced pressure, and the residue was adjusted to pH 1 by adding 1N HCI. The resulting solution was extracted with EtOAc (3 X 300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel using 10:1 petroleum ether/EtOAc as eluent provided the title compound (36 g, 99percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.44 (d, J = 1.60 Hz, 1 H), 7.62 (dd, J = 8.40, 2.40 Hz, 1 H), 7.25 (d, J = 8.40 Hz, 1 H), 4.69 (s, 2 H), 3.83 (s, 1 H).
99% at 0 - 20℃; for 2.5 h; Intermediate 2: (5-chloro-2-pyridinyl)methanol To a cooled (00C) solution of methyl 5-chloro-2-pyridinecarboxylate (43 g, 251 mmol) in methanol (400 ml.) was added NaBH4 (28.7 g, 754 mmol) in small portions over approximately 30 min. After addition, the reaction mixture was stirred at room temperature for 2 h, at which time TLC analysis showed the completion of the reaction. The reaction mixture was then concentrated under reduced pressure, and the residue was adjusted to pH 1 by adding 1N HCI. The resulting solution was extracted with EtOAc (3 X 300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel using 10:1 petroleum ether/EtOAc as eluent provided the title compound (36 g, 99percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.44 (d, J = 1.60 Hz, 1 H), 7.62 (dd, J = 8.40, 2.40 Hz, 1 H), 7.25 (d, J = 8.40 Hz, 1 H), 4.69 (s, 2 H), 3.83 (s, 1 H).
99% at 0 - 20℃; for 2.5 h; Intermediate 2: (5-chloro-2-pyridinyl)methanol To a cooled (00C) solution of methyl 5-chloro-2-pyridinecarboxylate (43 g, 251 mmol) in methanol (400 ml.) was added NaBH4 (28.7 g, 754 mmol) in small portions over approximately 30 min. After addition, the reaction mixture was stirred at room temperature for 2 h, at which time TLC analysis showed the completion of the reaction. The reaction mixture was then concentrated under reduced pressure, and the residue was adjusted to pH 1 by adding 1N HCI. The resulting solution was extracted with EtOAc (3 X 300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel using 10:1 petroleum ether/EtOAc as eluent provided the title compound (36 g, 99percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.44 (d, J = 1.60 Hz, 1 H), 7.62 (dd, J = 8.40, 2.40 Hz, 1 H), 7.25 (d, J = 8.40 Hz, 1 H), 4.69 (s, 2 H), 3.83 (s, 1 H).
99% at 0 - 20℃; for 2.5 h; Intermediate 2: (5-chloro-2-pyridinyl)methanolTo a cooled (00C) solution of methyl δ-chloro^-pyridinecarboxylate (43 g, 251 mmol) in methanol (400 ml.) was added NaBH4 (28.7 g, 754 mmol) in small portions over approximately 30 min. After addition, the reaction mixture was stirred at room temperature for 2 h, at which time TLC analysis showed the completion of the reaction. The reaction mixture was then concentrated under reduced pressure, and the residue was adjusted to pH 1 by adding 1 NHCI. The resulting solution was extracted with EtOAc (3 X 300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel using 10:1 petroleum ether/EtOAc as eluent provided the title compound (36 g, 99percent): 1H NMR (400 MHz, CDCI3) δ ppm 8.44 (d, J = 1.60 Hz, 1 H), 7.62 (dd, J = 8.40, 2.40 Hz, 1 H), 7.25 (d, J = 8.40 Hz, 1 H), 4.69 (s, 2 H), 3.83 (s, 1 H).
99% at 0 - 20℃; for 2.5 h; II. (5-chloro-2-pyridinyl)methanol To a cooled (0°C) solution of methyl 5-chloro-2-pyridinecarboxylate (43 g, 251 mmol) in methanol (400 mL) was added NaB (28.7 g, 754 mmol) in small portions over approximately 30 min. After addition, the reaction mixture was stirred at room temperature for 2 h, at which time TLC analysis showed the completion of the reaction. The reaction mixture was then concentrated under reduced pressure, and the residue was adjusted to pH 1 by adding IN HC1. The resulting solution was extracted with EtOAc (3 X 300 mL). The combined organic layers were dried (Na2SC>4) and evaporated. Flash chromatography of the residue over silica gel using 10: 1 petroleum ether/EtOAc as eluent provided the title compound (36 g, 99percent yield): FontWeight="Bold" FontSize="10" H NMR (400 MHz, CDC13) δ ppm 8.44 (d, J = 1.60 Hz, 1H), 7.62 (dd, J = 8.40, 2.40 Hz, 1H), 7.25 (d, J = 8.40 Hz, 1H), 4.69 (s, 2 H), 3.83 (s, 1Η).
95% at 20℃; for 4 h; 5-chloro-2(chloromethyl)pyridine; [00372] To a 0 °C solution of 5-chloropicolinic acid (3.00 g, 19.0 mmol) indichloromethane (20 mL) was added sulfurous dichloride (2.78 mL, 38.1 mmol), after which the reaction was warmed to room temperature and stirred at that temperature for 4 hours. The reaction was then concentrated to dryness, then reconstituted in dichloromethane (5 mL). Methanol (10 mL) was added to the reaction mixture, and the reaction was allowed to stir at room temperature for 12 hours, after which it was then diluted with water, extracted with ethyl acetate (3 x 50 mL), washed with water, then washed with saturated sodium bicarbonate solution, dried (magnesium sulfate), filtered and concentrated. Purification was achieved by silica gel chromatography (ISCO 80g) using 0 to 80percent ethyl acetate in hexanes to afford methyl 5-chloropicolinate was as an off-white solid (2.75 g, 15.2 mmol, 80percent yield ).[00373] To a 0 °C solution of methyl 5-chloropicolinate (2.70 g, 15.7 mmol) in methanol (50 mL) was added sodium borohydride (1.79 g, 47.2 mmol), after which the reaction was warmed to room temperature and stirred at that temperature for 4 hours. The reaction mixture was then concentrated to a residue which was treated with 1M hydrochloric acid solution (15 mL), extracted with ethyl acetate (3 x 100 mL), washed with water, then washed with saturated sodium bicarbonate solution, dried (magnesium sulfate), filtered and concentrated. Purification was achieved by silica gel chromatography (ISCO 80g) using 0 to 60percent ethyl acetate in hexanes to afford (5-chloropyridin-2-yl)methanol was as an off-white solid (2.15 g, 14.9 mmol, 95percent yield).[00374] To a 0 °C solution of (5-chloropyridin-2-yl)methanol (2.10 g, 14.6 mmol) in dichloromethane (10 mL) was added sulfurous dichloride (1.60 mL, 21.9 mmol) followed by N,N-dimethylformamide (50 μ), after which the reaction was warmed to room temperature and stirred at that temperature for 4 hours. The reaction mixture was then concentrated to a residue which was reconstituted in water (15 mL), ethyl acetate (15 mL), and saturated sodium bicarbonate solution (15 mL). The organic layers were separated and washed with saturated sodium chloride solution, dried (magnesium sulfate), filtered and concentrated. Purification was achieved by silica gel chromatography (ISCO 40g) using 0 to 50percent ethyl acetate in hexanes to afford 5-chloro-2(chloromethyl)pyridine as an light brown oil (2.11 g, 13.0 mmol, 89percent yield).
95% With sodium tetrahydroborate In methanol at 20℃; for 1 h; A solution of methyl 5-chloropicolinate (2 g, 1 1 .7 mmol) in MeOH (20 ml) and sodium borohydride (0.89 g, 23.3 mmol) was stirred at rt for 1 h. After reaction was completed, solvent was evaporated. Distilled water was added and the aqueous layer was extracted with dichloromethane (3 x 30 ml). The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to afford 1 .6 g (95percent yield) of (5- Chloropyridin-2-yl) methanol as colourless liquid.1H NMR (400 MHz, CDCI3): δ ppm 3.29 (br s, 1 H), 4.75 (br s, 2H), 7.25 (1 H, merged with CDCI3), 7.67 (d, J = 7.0 Hz, 1 H), 8.52 (s, 1 H).LC-MS: m/z 144.0 (M+H)+.

Reference: [1] Patent: WO2009/76387, 2009, A1, . Location in patent: Page/Page column 27
[2] Patent: WO2010/141538, 2010, A1, . Location in patent: Page/Page column 18-19
[3] Patent: WO2010/141539, 2010, A1, . Location in patent: Page/Page column 18-19
[4] Patent: WO2010/141545, 2010, A1, . Location in patent: Page/Page column 19-20
[5] Patent: WO2010/141540, 2010, A1, . Location in patent: Page/Page column 17-18
[6] Patent: WO2013/166621, 2013, A1, . Location in patent: Page/Page column 47; 48
[7] Patent: WO2012/88469, 2012, A1, . Location in patent: Page/Page column 152-153
[8] Patent: WO2014/167528, 2014, A1, . Location in patent: Page/Page column 55; 56
[9] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 3, p. 344 - 348
[10] Patent: US2006/287341, 2006, A1, . Location in patent: Page/Page column 47-48
[11] Patent: US2007/4772, 2007, A1, . Location in patent: Page/Page column 83
  • 22
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  • [ 107504-07-4 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 12, p. 5827 - 5833
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Ethyl 5-chloropicolinate

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