Home Cart 0 Sign in  

[ CAS No. 178876-82-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 178876-82-9
Chemical Structure| 178876-82-9
Structure of 178876-82-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 178876-82-9 ]

Related Doc. of [ 178876-82-9 ]

Alternatived Products of [ 178876-82-9 ]

Product Details of [ 178876-82-9 ]

CAS No. :178876-82-9 MDL No. :MFCD08062950
Formula : C7H7BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OQUCMNQHZFOMPC-UHFFFAOYSA-N
M.W : 231.05 Pubchem ID :10704661
Synonyms :

Safety of [ 178876-82-9 ]

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

Application In Synthesis of [ 178876-82-9 ]

* 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 [ 178876-82-9 ]
  • Downstream synthetic route of [ 178876-82-9 ]

[ 178876-82-9 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 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
  • 2
  • [ 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
  • 3
  • [ 1824-81-3 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
Reference: [1] Patent: US2011/201605, 2011, A1,
[2] Patent: WO2011/101304, 2011, A2,
  • 4
  • [ 5327-33-3 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
Reference: [1] Patent: US2011/201605, 2011, A1,
[2] Patent: WO2011/101304, 2011, A2,
  • 5
  • [ 26893-72-1 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
Reference: [1] Patent: US2011/201605, 2011, A1,
[2] Patent: WO2011/101304, 2011, A2,
  • 6
  • [ 23628-31-1 ]
  • [ 443956-21-6 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
Reference: [1] Patent: US2011/152312, 2011, A1,
[2] Patent: WO2011/75591, 2011, A1,
  • 7
  • [ 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
  • 8
  • [ 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
  • 9
  • [ 67-56-1 ]
  • [ 875051-78-8 ]
  • [ 178876-82-9 ]
YieldReaction ConditionsOperation in experiment
26%
Stage #1: With potassium permanganate In water at 80℃; for 3.75 h;
Stage #2: With sodium sulfite In water
Preparation 2. 6-Amino-5-bromo-pyridine-2-carboxvlic acid methyl ester. Potassium permanganate (144 g, 916 mmol) solution in water (1.4 L) was added dropwise over 45 minutes to a solution of the product of Preparation 1 (60 g, 262 mmol) in water (1.8 L) at 8O0C. The mixture was stirred at 8O0C for 3 hours and then sodium sulphite solution (200 mL, 1 N aqueous, 200 mmol) was added dropwise and the mixture filtered through Arbocel.(R). whilst still hot. The mixture was concentrated in vacuo to 1 L total volume and then extracted with ethyl acetate (8 x 400 mL). The aqueous was then concentrated to dryness in vacuo and azeotroped with methanol (3 x 250 mL). The resulting off-white solid was slurried in methanol (800 mL) and concentrated sulphuric acid (30 mL) added dropwise. The mixture was heated at 8O0C for 16 hours before filtering and evaporating to dryness in vacuo. The residue was dissolved in water (600 mL), basified with sodium bicarbonate solution and then extracted with ethyl acetate (3 x 400 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to afford the title compound as a white solid in 26percent yield, 15.8g.1H NMR (400MHz, CD3OD) δ: 3.90(s, 3H), 7.25(d, 1H), 7.88(d, 1H) LRMS: m/z ES 232 [MH]+Microanalysis: C7H7BrN2O2 requires: C 36.39; H 3.05 N 12.12; found C 36.24; H 3.08, N 11.94
Reference: [1] Patent: WO2007/83239, 2007, A1, . Location in patent: Page/Page column 35-36
  • 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
  • 11
  • [ 67-56-1 ]
  • [ 875051-81-3 ]
  • [ 178876-82-9 ]
Reference: [1] Patent: WO2006/11050, 2006, A2, . Location in patent: Page/Page column 46-47
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 6, p. 650 - 654
  • 12
  • [ 26893-72-1 ]
  • [ 178876-82-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 4026 - 4030
[2] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[3] Patent: US2011/190269, 2011, A1,
[4] Patent: WO2011/92272, 2011, A1,
  • 13
  • [ 1824-81-3 ]
  • [ 178876-82-9 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[2] Patent: US2011/190269, 2011, A1,
[3] Patent: WO2011/92272, 2011, A1,
  • 14
  • [ 5327-33-3 ]
  • [ 178876-82-9 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[2] Patent: US2011/190269, 2011, A1,
[3] Patent: WO2011/92272, 2011, A1,
  • 15
  • [ 126325-46-0 ]
  • [ 178876-82-9 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 6, p. 650 - 654
  • 16
  • [ 875051-78-8 ]
  • [ 178876-82-9 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 6, p. 650 - 654
  • 17
  • [ 1824-81-3 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
Reference: [1] Patent: US2011/201605, 2011, A1,
[2] Patent: WO2011/101304, 2011, A2,
  • 18
  • [ 5327-33-3 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
Reference: [1] Patent: US2011/201605, 2011, A1,
[2] Patent: WO2011/101304, 2011, A2,
  • 19
  • [ 26893-72-1 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
Reference: [1] Patent: US2011/201605, 2011, A1,
[2] Patent: WO2011/101304, 2011, A2,
  • 20
  • [ 23628-31-1 ]
  • [ 443956-21-6 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
Reference: [1] Patent: US2011/152312, 2011, A1,
[2] Patent: WO2011/75591, 2011, A1,
  • 21
  • [ 67-56-1 ]
  • [ 875208-79-0 ]
  • [ 1221629-04-4 ]
  • [ 178876-82-9 ]
Reference: [1] Organic Process Research and Development, 2010, vol. 14, # 1, p. 263 - 271
  • 22
  • [ 178876-82-9 ]
  • [ 178876-86-3 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
  • 23
  • [ 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
  • 24
  • [ 23628-31-1 ]
  • [ 443956-21-6 ]
  • [ 178876-83-0 ]
  • [ 178876-82-9 ]
Reference: [1] Patent: US2011/152312, 2011, A1,
[2] Patent: WO2011/75591, 2011, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 178876-82-9 ]

Bromides

Chemical Structure| 29682-15-3

[ 29682-15-3 ]

Methyl 5-bromopicolinate

Similarity: 0.90

Chemical Structure| 885326-88-5

[ 885326-88-5 ]

Methyl 6-amino-4-bromopicolinate

Similarity: 0.88

Chemical Structure| 77199-09-8

[ 77199-09-8 ]

Ethyl 5-bromopicolinate

Similarity: 0.87

Chemical Structure| 886365-06-6

[ 886365-06-6 ]

Methyl 5-bromo-4-methylpicolinate

Similarity: 0.84

Chemical Structure| 845306-08-3

[ 845306-08-3 ]

tert-Butyl 5-bromopicolinate

Similarity: 0.84

Esters

Chemical Structure| 29682-15-3

[ 29682-15-3 ]

Methyl 5-bromopicolinate

Similarity: 0.90

Chemical Structure| 885326-88-5

[ 885326-88-5 ]

Methyl 6-amino-4-bromopicolinate

Similarity: 0.88

Chemical Structure| 77199-09-8

[ 77199-09-8 ]

Ethyl 5-bromopicolinate

Similarity: 0.87

Chemical Structure| 36052-26-3

[ 36052-26-3 ]

Methyl 6-aminopicolinate

Similarity: 0.85

Chemical Structure| 845306-08-3

[ 845306-08-3 ]

tert-Butyl 5-bromopicolinate

Similarity: 0.84

Amines

Chemical Structure| 885326-88-5

[ 885326-88-5 ]

Methyl 6-amino-4-bromopicolinate

Similarity: 0.88

Chemical Structure| 36052-26-3

[ 36052-26-3 ]

Methyl 6-aminopicolinate

Similarity: 0.85

Chemical Structure| 69142-64-9

[ 69142-64-9 ]

Ethyl 6-aminopicolinate

Similarity: 0.83

Chemical Structure| 1072448-08-8

[ 1072448-08-8 ]

Methyl 3-amino-5-bromopicolinate

Similarity: 0.81

Chemical Structure| 178876-83-0

[ 178876-83-0 ]

Methyl 6-amino-3-bromopicolinate

Similarity: 0.77

Related Parent Nucleus of
[ 178876-82-9 ]

Pyridines

Chemical Structure| 29682-15-3

[ 29682-15-3 ]

Methyl 5-bromopicolinate

Similarity: 0.90

Chemical Structure| 885326-88-5

[ 885326-88-5 ]

Methyl 6-amino-4-bromopicolinate

Similarity: 0.88

Chemical Structure| 77199-09-8

[ 77199-09-8 ]

Ethyl 5-bromopicolinate

Similarity: 0.87

Chemical Structure| 36052-26-3

[ 36052-26-3 ]

Methyl 6-aminopicolinate

Similarity: 0.85

Chemical Structure| 845306-08-3

[ 845306-08-3 ]

tert-Butyl 5-bromopicolinate

Similarity: 0.84