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[ CAS No. 36052-26-3 ] {[proInfo.proName]}

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Chemical Structure| 36052-26-3
Chemical Structure| 36052-26-3
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Product Details of [ 36052-26-3 ]

CAS No. :36052-26-3 MDL No. :MFCD00233712
Formula : C7H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OHIHEJTUXNQOPM-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :13809143
Synonyms :

Calculated chemistry of [ 36052-26-3 ]

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 : 1.0
Molar Refractivity : 39.92
TPSA : 65.21 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) : -6.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.38
Log Po/w (XLOGP3) : 0.69
Log Po/w (WLOGP) : 0.46
Log Po/w (MLOGP) : 0.15
Log Po/w (SILICOS-IT) : 0.47
Consensus Log Po/w : 0.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.49
Solubility : 4.93 mg/ml ; 0.0324 mol/l
Class : Very soluble
Log S (Ali) : -1.64
Solubility : 3.51 mg/ml ; 0.0231 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.73
Solubility : 2.87 mg/ml ; 0.0188 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.6

Safety of [ 36052-26-3 ]

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 [ 36052-26-3 ]

* 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 [ 36052-26-3 ]
  • Downstream synthetic route of [ 36052-26-3 ]

[ 36052-26-3 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 36052-26-3 ]
  • [ 2032-35-1 ]
  • [ 88047-55-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 1159 - 1164
  • 2
  • [ 36052-26-3 ]
  • [ 79651-64-2 ]
YieldReaction ConditionsOperation in experiment
32% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 13 h; (6-methylpyridin-2-yl) methanol (5) [2]: To a solution of LiAlH4 (86 g, 2.25ml) in 500ml anhydrous THF was added dropwise(over 1 h) the methyl 6-aminopicolinate 4 (114 g, 0.75 mol) in the solution of 200ml anhydrous THF at 0 °C.
The reaction mixture was stirred over 12h under the room temperature until TLC showed no starting material remained. Na2SO4.10H2O (442.8 g, 2.7mol) was added the mixture in portions and the reaction mixture was stirred at room temperature for another 2h.
Then the mixture was filtered through a pad of Celite, and the Celite cake was washed with THF(2*200mL).
The filtrate was concentrated under reduced pressure, the residue was purified by chromatography (DCM/Methol, 30/1) to give (6-methylpyridin-2-yl) compound 5 (29.8g, 32percent).
1H-NMR (d6-DMSO, 300MHz): δ 4.30 (s, 2H) ; 5.26 (m, 1H, OH); 5.78(br, 2H, NH); 6.27(d, 1H); 6.57(d, 1H); 7.34 (t, 1H).
Reference: [1] Patent: EP3018125, 2016, A1, . Location in patent: Paragraph 0543-0544; 0549-0550
[2] Patent: WO2004/101533, 2004, A1, . Location in patent: Page 79
  • 3
  • [ 36052-26-3 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
YieldReaction ConditionsOperation in experiment
22% With bromine In chloroform at 20℃; for 40 h; d) 6-Amino-5-bromo-pyridine-2-carboxylic acid methyl ester; To a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHCl3 (100 mL) at room temperature and stirred for 40 hours. The reaction mixture was diluted with CHCl3 and washed with saturated sodium thiosulfate solution and water. The organic phase was dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel column chromatography using ethyl acetate/hexane as eluent. The title compound obtained as yellow solid (3.3 g, 22percent).MS ESI (m/e): 231.0 [(M+H)+].1H NMR (CDCl3, 400 MHz): δ(ppm)=7.76 (d, J=7.88 Hz, 1H), 7.34 (d, J=7.92 Hz, 1H), 5.23 (s, 2H), 3.94 (s, 3H).d) 6-Amino-3-bromo-pyridine-2-carboxylic acid methyl esterIn step d) the isomeric 6-amino-3-bromo-pyridine-2-carboxylic acid methyl ester (3.0 g, 19percent) was isolated as side product.MS ESI (m/e): 231.2 [(M+H)+].1H NMR (CDCl3, 400 MHz): δ(ppm)=7.60 (d, J=8.72 Hz, 1H), 6.47 (d, J=7.88 Hz, 1H), 4.71 (s, 2H), 3.94 (s, 3H).
22% With bromine In chloroform at 20℃; for 40 h; To a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHC13 (100 mL) at room temperature and stirred for 40 hours. The reaction mixture was diluted with CHC13 and washed with saturated sodium thiosulfate solution and water. The organic phase was dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel column chromatography using ethyl acetate/hexane as eluent. The title compound obtained as yellow solid (3.3g, 22percent). MS ESI (m/e): 231.0 [(M+H)+].1H NMR (CDC13, 400 MHz): <5 (ppm) = 7.76 (d, J = 7.88 Hz, 1H), 7.34 (d, J = 7.92 Hz, 1H), 5.23 (s, 2H), 3.94 (s, 3H).
22% With bromine In chloroform at 20℃; for 40 h; d) 6-Amino-5-bromo-pyridine-2-carboxylic acid methyl ester; To a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHCl3 (100 mL) at room temperature and stirred for 40 hours. The reaction mixture was diluted with CHCl3 and washed with saturated sodium thiosulfate solution and water. The organic phase was dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel column chromatography using ethyl acetate/hexane as eluent. The title compound obtained as yellow solid (3.3 g, 22percent).MS ESI (m/e): 231.0 [(M+H)+].1H NMR (CDCl3, 400 MHz): δ (ppm)=7.76 (d, J=7.88 Hz, 1H), 7.34 (d, J=7.92 Hz, 1H), 5.23 (s, 2H), 3.94 (s, 3H).
22% With bromine In chloroform at 20℃; for 40 h; d) 6-Amino-5-bromo-pyridine-2-carboxylic acid methyl esterTo a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHC13 (100 mL) at room temperature and stirred for 40 hours. The reaction mixture was diluted with CHC13 and washed with saturated sodium thiosulfate solution and water. The organic phase was dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel column chromatography using ethyl acetate/hexane as eluent. The title compound obtained as yellow solid (3.3 g, 22percent). MS ESI (m/e): 231.0 [(M+H)+].1H NMR (CDC13, 400 MHz): <5 (ppm) = 7.76 (d, J= 7.88 Hz, 1H), 7.34 (d, J= 7.92 Hz, 1H), 5.23 (s, 2H), 3.94 (s, 3H). d') 6-Amino-3-bromo-pyridine-2-carboxylic acid methyl esterIn step d) the isomeric 6-amino-3-bromo-pyridine-2-carboxylic acid methyl ester (3.0g, 19percent) was isolated as side product.MS ESI (m/e): 231.2 [(M+H)+].1H NMR (CDC13, 400 MHz): <5 (ppm) = 7.60 (d, J= 8.72 Hz, 1H), 6.47 (d, J= 7.88 Hz, 1H), 4.71 (s, 2H), 3.94(s, 3H).

Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[2] Organic Process Research and Development, 2010, vol. 14, # 1, p. 263 - 271
[3] Tetrahedron Letters, 2010, vol. 51, # 38, p. 5035 - 5037
[4] Patent: US2011/190269, 2011, A1, . Location in patent: Page/Page column 61-62
[5] Patent: WO2011/92272, 2011, A1, . Location in patent: Page/Page column 129; 130
[6] Patent: US2011/201605, 2011, A1, . Location in patent: Page/Page column 45
[7] Patent: WO2011/101304, 2011, A2, . Location in patent: Page/Page column 92
[8] Patent: WO2009/140101, 2009, A2, . Location in patent: Page/Page column 42
  • 4
  • [ 36052-26-3 ]
  • [ 178876-83-0 ]
YieldReaction ConditionsOperation in experiment
29%
Stage #1: at 10 - 35℃; for 7 h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
Reference Example 17; methyl 6-amino-3-bromopyridine-2-carboxylate [Show Image]; To a suspension of methyl 6-aminopyridine-2-carboxylate (5.98 g, 39.5 mmol) and sodium carbonate (2.64 g, 24.9 mmol) in acetic acid (150 mL) was added bromine (7.89 g, 49.4 mmol), and the mixture was stirred at room temperature for 7 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine. This was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70-->80/20) to give the title compound (2.67 g, yield 29percent). 1H-NMR (CDCl3) δ: 3.95 (3H, s), 4.74 (2H, brs), 6.49 (1H, d, J = 8.8 Hz), 7.62 (1H, d, J = 8.8 Hz), MS (ESI+): 231 (M+H).
11% With bromine; sodium carbonate In acetic acid at 20℃; for 5 h; To a 100 mL round bottom flask, were added methyl 6-aminopicolinate (6 g, 0.0394 mol), sodium carbonate (2.64 g, 0.0248 mol) and acetic acid (300 mL). The reaction mixture was cooled to 0 - 5 °C. To the same flask, bromine (2 mL, 0.039 mol) was slowly added. The reaction mixture was stirred at room temperature for 5 h. The volatiles were evaporated under reduced pressure to get the residue. The residue was neutralized with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to get the crude product. The crude product was purified by column chromatography using 60 - 120 silica gel and 30 percent ethyl acetate in hexane to get the title compound [1 g, 11 percent]. FontWeight="Bold" FontSize="10" H NMR (400 MHZ, CDC13): δ 7.63 (d, / = 8.8 Hz, 1H), 6.51 (d, = 8.8 Hz, 1H), 4.80 (brs, 2H), 3.94 (s, 3H); LC-MS: 232.8 [M+2H]+.
Reference: [1] Patent: EP2098513, 2009, A1, . Location in patent: Page/Page column 49
[2] Patent: WO2014/125426, 2014, A1, . Location in patent: Page/Page column 59; 60
  • 5
  • [ 36052-26-3 ]
  • [ 443956-21-6 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
YieldReaction ConditionsOperation in experiment
18% With bromine In chloroform at 20℃; b. A solution of bromine (2.57 ml) in chloroform (40 mL) was slowly added over 30 minutes to a solution of 6-aminopyridine-2-carboxylic acid methyl ester (6.92 g) in chloroform (300 mL). The mixture was stirred overnight at room temperature and then loaded on silica and purified by chromatography (Si02, Heptane/EA) to afford 6-amino-5-bromopyridine-2-carboxylic acid methyl ester as a solid (2 g, 19percent) along with 6-amino-3-bromopyridine-2-carboxylic acid methyl ester (3 g, 29percent) and 6-amino-3,5-dibromopyridine-2-carboxylic acid methyl ester (2.6 g, 18percent). 1H NMR (400 MHz, CHLOROFORM-d): 3.97 (s, 3H), 5.22 (br. s., 2H), 7.38 (d, J=7.8 Hz, 1H) and 7.79 (d, J=7.8 Hz, 1H)
19% With bromine In chloroform at 20℃; b. A solution of bromine (2.57 ml) in chloroform (40 mL) was slowly added over 30 minutes to a solution of 6-aminopyridine-2-carboxylic acid methyl ester (6.92 g) in chloroform (300 mL). The mixture was stirred overnight at room temperature and then loaded on silica and purified by chromatography (SiO2, Heptane/EA) to afford 6-amino-5-bromopyridine-2-carboxylic acid methyl ester as a solid (2 g, 19percent) along with 6-amino-3-bromopyridine-2-carboxylic acid methyl ester (3 g, 29percent) and 6-amino-3,5-dibromopyridine-2-carboxylic acid methyl ester (2.6 g, 18percent). 1H NMR (400 MHz, CHLOROFORM-d): 3.97 (s, 3H), 5.22 (br. s., 2H), 7.38 (d, J=7.8 Hz, 1H) and 7.79 (d, J=7.8 Hz, 1H)
Reference: [1] Patent: WO2011/75591, 2011, A1, . Location in patent: Page/Page column 95
[2] Patent: US2011/152312, 2011, A1, . Location in patent: Page/Page column 40
  • 6
  • [ 36052-26-3 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
YieldReaction ConditionsOperation in experiment
22% With bromine In chloroform at 20℃; for 40 h; d) 6-Amino-5-bromo-pyridine-2-carboxylic acid methyl ester; To a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHCl3 (100 mL) at room temperature and stirred for 40 hours. The reaction mixture was diluted with CHCl3 and washed with saturated sodium thiosulfate solution and water. The organic phase was dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel column chromatography using ethyl acetate/hexane as eluent. The title compound obtained as yellow solid (3.3 g, 22percent).MS ESI (m/e): 231.0 [(M+H)+].1H NMR (CDCl3, 400 MHz): δ(ppm)=7.76 (d, J=7.88 Hz, 1H), 7.34 (d, J=7.92 Hz, 1H), 5.23 (s, 2H), 3.94 (s, 3H).d) 6-Amino-3-bromo-pyridine-2-carboxylic acid methyl esterIn step d) the isomeric 6-amino-3-bromo-pyridine-2-carboxylic acid methyl ester (3.0 g, 19percent) was isolated as side product.MS ESI (m/e): 231.2 [(M+H)+].1H NMR (CDCl3, 400 MHz): δ(ppm)=7.60 (d, J=8.72 Hz, 1H), 6.47 (d, J=7.88 Hz, 1H), 4.71 (s, 2H), 3.94 (s, 3H).
22% With bromine In chloroform at 20℃; for 40 h; To a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHC13 (100 mL) at room temperature and stirred for 40 hours. The reaction mixture was diluted with CHC13 and washed with saturated sodium thiosulfate solution and water. The organic phase was dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel column chromatography using ethyl acetate/hexane as eluent. The title compound obtained as yellow solid (3.3g, 22percent). MS ESI (m/e): 231.0 [(M+H)+].1H NMR (CDC13, 400 MHz): <5 (ppm) = 7.76 (d, J = 7.88 Hz, 1H), 7.34 (d, J = 7.92 Hz, 1H), 5.23 (s, 2H), 3.94 (s, 3H).
22% With bromine In chloroform at 20℃; for 40 h; d) 6-Amino-5-bromo-pyridine-2-carboxylic acid methyl ester; To a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHCl3 (100 mL) at room temperature and stirred for 40 hours. The reaction mixture was diluted with CHCl3 and washed with saturated sodium thiosulfate solution and water. The organic phase was dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel column chromatography using ethyl acetate/hexane as eluent. The title compound obtained as yellow solid (3.3 g, 22percent).MS ESI (m/e): 231.0 [(M+H)+].1H NMR (CDCl3, 400 MHz): δ (ppm)=7.76 (d, J=7.88 Hz, 1H), 7.34 (d, J=7.92 Hz, 1H), 5.23 (s, 2H), 3.94 (s, 3H).
22% With bromine In chloroform at 20℃; for 40 h; d) 6-Amino-5-bromo-pyridine-2-carboxylic acid methyl esterTo a solution of 6-amino-pyridine-2-carboxylic acid methyl ester (10 g, 66.0 mmol) in chloroform (450 mL) was added bromine (3.4 mL, 66.0 mmol) in CHC13 (100 mL) at room temperature and stirred for 40 hours. The reaction mixture was diluted with CHC13 and washed with saturated sodium thiosulfate solution and water. The organic phase was dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel column chromatography using ethyl acetate/hexane as eluent. The title compound obtained as yellow solid (3.3 g, 22percent). MS ESI (m/e): 231.0 [(M+H)+].1H NMR (CDC13, 400 MHz): <5 (ppm) = 7.76 (d, J= 7.88 Hz, 1H), 7.34 (d, J= 7.92 Hz, 1H), 5.23 (s, 2H), 3.94 (s, 3H). d') 6-Amino-3-bromo-pyridine-2-carboxylic acid methyl esterIn step d) the isomeric 6-amino-3-bromo-pyridine-2-carboxylic acid methyl ester (3.0g, 19percent) was isolated as side product.MS ESI (m/e): 231.2 [(M+H)+].1H NMR (CDC13, 400 MHz): <5 (ppm) = 7.60 (d, J= 8.72 Hz, 1H), 6.47 (d, J= 7.88 Hz, 1H), 4.71 (s, 2H), 3.94(s, 3H).

Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[2] Organic Process Research and Development, 2010, vol. 14, # 1, p. 263 - 271
[3] Tetrahedron Letters, 2010, vol. 51, # 38, p. 5035 - 5037
[4] Patent: US2011/190269, 2011, A1, . Location in patent: Page/Page column 61-62
[5] Patent: WO2011/92272, 2011, A1, . Location in patent: Page/Page column 129; 130
[6] Patent: US2011/201605, 2011, A1, . Location in patent: Page/Page column 45
[7] Patent: WO2011/101304, 2011, A2, . Location in patent: Page/Page column 92
[8] Patent: WO2009/140101, 2009, A2, . Location in patent: Page/Page column 42
  • 7
  • [ 36052-26-3 ]
  • [ 178876-82-9 ]
YieldReaction ConditionsOperation in experiment
24.1% With bromine In dichloromethane at 20℃; A solution of bromine (5.25 g, 32.9 mmol) in dichloromethane (10 mL) was added dropwise to a solution of methyl 6-aminopicolinate (5.0 g, 32.9 mmol) in dichloromethane The resulting mixture was stirred at room temperature overnight. Saturated aqueous sodium bicarbonate (40 mL) was added, the layers were separated and the organic layer was collected. The aqueous layer was extracted with dichloromethane (70 mL) and the combined organic layers were washed sequentially with saturated aqueous sodium thiosulfate (20 mL) and saturated brine (20 mL) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the product was purified by column chromatography (200~300 mesh silica gel, ethyl acetate: petroleum ether = 1: 20~1: 5) to give methyl 6-amino-5- bromopicolinate 11) (1.83 g). The yield was 24.1percent /
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 4026 - 4030
[2] Patent: CN107286156, 2017, A, . Location in patent: Paragraph 0081-0083
[3] Patent: WO2006/21448, 2006, A1, . Location in patent: Page/Page column 53
[4] Patent: US2010/324030, 2010, A1, . Location in patent: Page/Page column 10
  • 8
  • [ 36052-26-3 ]
  • [ 443956-21-6 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
YieldReaction ConditionsOperation in experiment
18% With bromine In chloroform at 20℃; b. A solution of bromine (2.57 ml) in chloroform (40 mL) was slowly added over 30 minutes to a solution of 6-aminopyridine-2-carboxylic acid methyl ester (6.92 g) in chloroform (300 mL). The mixture was stirred overnight at room temperature and then loaded on silica and purified by chromatography (Si02, Heptane/EA) to afford 6-amino-5-bromopyridine-2-carboxylic acid methyl ester as a solid (2 g, 19percent) along with 6-amino-3-bromopyridine-2-carboxylic acid methyl ester (3 g, 29percent) and 6-amino-3,5-dibromopyridine-2-carboxylic acid methyl ester (2.6 g, 18percent). 1H NMR (400 MHz, CHLOROFORM-d): 3.97 (s, 3H), 5.22 (br. s., 2H), 7.38 (d, J=7.8 Hz, 1H) and 7.79 (d, J=7.8 Hz, 1H)
19% With bromine In chloroform at 20℃; b. A solution of bromine (2.57 ml) in chloroform (40 mL) was slowly added over 30 minutes to a solution of 6-aminopyridine-2-carboxylic acid methyl ester (6.92 g) in chloroform (300 mL). The mixture was stirred overnight at room temperature and then loaded on silica and purified by chromatography (SiO2, Heptane/EA) to afford 6-amino-5-bromopyridine-2-carboxylic acid methyl ester as a solid (2 g, 19percent) along with 6-amino-3-bromopyridine-2-carboxylic acid methyl ester (3 g, 29percent) and 6-amino-3,5-dibromopyridine-2-carboxylic acid methyl ester (2.6 g, 18percent). 1H NMR (400 MHz, CHLOROFORM-d): 3.97 (s, 3H), 5.22 (br. s., 2H), 7.38 (d, J=7.8 Hz, 1H) and 7.79 (d, J=7.8 Hz, 1H)
Reference: [1] Patent: WO2011/75591, 2011, A1, . Location in patent: Page/Page column 95
[2] Patent: US2011/152312, 2011, A1, . Location in patent: Page/Page column 40
  • 9
  • [ 36052-26-3 ]
  • [ 178876-86-3 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
  • 10
  • [ 36052-26-3 ]
  • [ 443956-21-6 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
YieldReaction ConditionsOperation in experiment
18% With bromine In chloroform at 20℃; b. A solution of bromine (2.57 ml) in chloroform (40 mL) was slowly added over 30 minutes to a solution of 6-aminopyridine-2-carboxylic acid methyl ester (6.92 g) in chloroform (300 mL). The mixture was stirred overnight at room temperature and then loaded on silica and purified by chromatography (Si02, Heptane/EA) to afford 6-amino-5-bromopyridine-2-carboxylic acid methyl ester as a solid (2 g, 19percent) along with 6-amino-3-bromopyridine-2-carboxylic acid methyl ester (3 g, 29percent) and 6-amino-3,5-dibromopyridine-2-carboxylic acid methyl ester (2.6 g, 18percent). 1H NMR (400 MHz, CHLOROFORM-d): 3.97 (s, 3H), 5.22 (br. s., 2H), 7.38 (d, J=7.8 Hz, 1H) and 7.79 (d, J=7.8 Hz, 1H)
19% With bromine In chloroform at 20℃; b. A solution of bromine (2.57 ml) in chloroform (40 mL) was slowly added over 30 minutes to a solution of 6-aminopyridine-2-carboxylic acid methyl ester (6.92 g) in chloroform (300 mL). The mixture was stirred overnight at room temperature and then loaded on silica and purified by chromatography (SiO2, Heptane/EA) to afford 6-amino-5-bromopyridine-2-carboxylic acid methyl ester as a solid (2 g, 19percent) along with 6-amino-3-bromopyridine-2-carboxylic acid methyl ester (3 g, 29percent) and 6-amino-3,5-dibromopyridine-2-carboxylic acid methyl ester (2.6 g, 18percent). 1H NMR (400 MHz, CHLOROFORM-d): 3.97 (s, 3H), 5.22 (br. s., 2H), 7.38 (d, J=7.8 Hz, 1H) and 7.79 (d, J=7.8 Hz, 1H)
Reference: [1] Patent: WO2011/75591, 2011, A1, . Location in patent: Page/Page column 95
[2] Patent: US2011/152312, 2011, A1, . Location in patent: Page/Page column 40
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Methyl 6-amino-5-bromopicolinate

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Chemical Structure| 178876-83-0

[ 178876-83-0 ]

Methyl 6-amino-3-bromopicolinate

Similarity: 0.81

Related Parent Nucleus of
[ 36052-26-3 ]

Pyridines

Chemical Structure| 69142-64-9

[ 69142-64-9 ]

Ethyl 6-aminopicolinate

Similarity: 0.97

Chemical Structure| 23628-31-1

[ 23628-31-1 ]

6-Aminopicolinic acid

Similarity: 0.90

Chemical Structure| 885326-88-5

[ 885326-88-5 ]

Methyl 6-amino-4-bromopicolinate

Similarity: 0.87

Chemical Structure| 178876-82-9

[ 178876-82-9 ]

Methyl 6-amino-5-bromopicolinate

Similarity: 0.85

Chemical Structure| 13509-13-2

[ 13509-13-2 ]

Methyl 4-methylpicolinate

Similarity: 0.85