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Chemical Structure| 29064-82-2
Chemical Structure| 29064-82-2
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Product Details of [ 29064-82-2 ]

CAS No. :29064-82-2 MDL No. :MFCD08275122
Formula : C7H3BrClNS Boiling Point : -
Linear Structure Formula :- InChI Key :FXIKIVFBAQCMRY-UHFFFAOYSA-N
M.W : 248.53 Pubchem ID :18450773
Synonyms :

Safety of [ 29064-82-2 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H317-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 29064-82-2 ]

* 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 [ 29064-82-2 ]
  • Downstream synthetic route of [ 29064-82-2 ]

[ 29064-82-2 ] Synthesis Path-Upstream   1~11

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YieldReaction ConditionsOperation in experiment
32%
Stage #1: for 4 h; Heating / reflux
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
A stirred mixture of 3-bromo-5H-thieno[3,2-c]pyridine-4-one (1.16 g, 5.04 mmol) and phosphorus oxychloride (20 ml) was heated to reflux for 4 h. The reaction was then allowed to cool to room temperature and the phosphorus oxychloride removed in vacuo. The residue was dissolved in DCM (25 ml) and washed with distilled water (2.x.25 ml) followed by saturated sodium hydrogen carbonate solution (25 ml). The organic layer was dried (MgSO4), filtered and the solvent removed in vacuo. The crude residue was then subjected to flash column chromatography (eluent petroleum spirit 40-60° C.:EtOAc, 5:1, Rf 0.5) to afford the title compound as a yellow solid (398 mg, 32percent).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 250 - 254
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1167 - 1171
[3] Patent: US2007/161672, 2007, A1, . Location in patent: Page/Page column 8
[4] Patent: WO2004/100947, 2004, A2, . Location in patent: Page 27; 17
[5] Patent: US2005/20619, 2005, A1, . Location in patent: Page 17
[6] Patent: US2005/43347, 2005, A1, . Location in patent: Page/Page column 26
[7] Patent: WO2016/207217, 2016, A1, . Location in patent: Page/Page column 111-112
  • 2
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Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 10, p. 3849 - 3855
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1246 - 1249
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Reference: [1] Patent: US2005/26944, 2005, A1,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 250 - 254
  • 5
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 250 - 254
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 250 - 254
  • 7
  • [ 16694-17-0 ]
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Reference: [1] Patent: WO2016/207217, 2016, A1,
  • 8
  • [ 1150566-09-8 ]
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Reference: [1] Patent: WO2016/207217, 2016, A1,
  • 9
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  • [ 799293-85-9 ]
YieldReaction ConditionsOperation in experiment
94% With ammonia In 1,4-dioxane; water at 150℃; for 18 h; A mixture of 3-bromo-4-chlorothieno[3,2-c]pyridine (prepared according to the procedure described in Bull. Soc. Chim. Belges 1970, 79, 407-414, 3 g, 12 mmol), concentrated aqueous NH4OH (100 mL), and p-dioxane (100 mL) was sealed in a stainless steel, high-pressure reactor and stirred for 18 hours at 150 C. The mixture was concentrated to half its original volume, diluted with water, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide 2.6 g (94percent) of the desired product. 1H NMR (DMSO-d6, 400 MHz) ? 7.83 (d, 1H), 7.77 (s, 1H), 7.26 (d, 1H), 6.48 (br s, 2H); MS m/e 229 (M+H)+.
94% With ammonia In 1,4-dioxane; water at 150℃; for 18 h; EXAMPLE 219A
3-bromothieno[3,2-c]pyridin-4-amine
A mixture of 3-bromo-4-chlorothieno[3,2-c]pyridine (prepared according to the procedure described in Bull. Soc. Chim. Belges 1970, 79, 407-414, 3 g, 12 mmol), concentrated aqueous NH4OH (100 mL), and p-dioxane (100 mL) was sealed in a stainless steel, high-pressure reactor and stirred for 18 hours at 150° C.
The mixture was concentrated to half its original volume, diluted with water, and extracted with ethyl acetate.
The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide 2.6 g (94percent) of the desired product. 1H NMR (DMSO-d6, 400 MHz) δ 7.83 (d, 1H), 7.77 (s, 1H), 7.26 (d, 1H), 6.48 (br s, 2H); MS m/e 229 (M+H)+.
84 mg With ammonium chloride In 1-methyl-pyrrolidin-2-one at 150℃; for 3 h; Microwave irradiation 3-Bromo-4-chloro-thieno[3,2-c]pyridine (300 mg, 1.21 mmol) was dissolved in NMP (3 mL) and placed in a 20-mL microwave vial. A saturated solution of NH4CI (5 mL) was added to the vial and the mixture was microwave heated at 150 °C for a total time of 3 h. The mixture was then diluted with water and extracted with ethyl acetate. The aqueous solution was then basified with NaOH and extracted with AcOEt. The latter solution was dried with Na2S04 and evaporated to dryness. The residue was purified by flash column chromatography over silica gel eluting with DCM to yield 3-bromo-thieno[3,2-c]pyridin-4-ylamine (84 mg). HPLC (254 nm): Rt: 4.38 min. HRMS (ESI) calcd for C7H5BrN2S [M+H]+ 228.9430, found 228.9441. 1 H NMR (500 MHz, DMSO-d6) delta ppm: 6.49 (s, 2 H) 7.27 (d, J=5.64 Hz, 1 H) 7.78 (s, 1 H) 7.83 (d, J=5.64 Hz, 1 H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1167 - 1171
[2] Patent: US2005/20619, 2005, A1, . Location in patent: Page 47
[3] Patent: US2005/43347, 2005, A1, . Location in patent: Page/Page column 56
[4] Journal of Organic Chemistry, 2009, vol. 74, # 10, p. 3849 - 3855
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 1, p. 250 - 254
[6] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1246 - 1249
[7] Patent: WO2004/100947, 2004, A2, . Location in patent: Page 27; 17
[8] Patent: US2005/20619, 2005, A1, . Location in patent: Page 17
[9] Patent: US2005/43347, 2005, A1, . Location in patent: Page/Page column 26
[10] Patent: WO2017/220477, 2017, A1, . Location in patent: Page/Page column 28-29
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Reference: [1] Patent: US2005/26944, 2005, A1,
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Reference: [1] Patent: US2005/26944, 2005, A1,
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