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[ CAS No. 249291-79-0 ]

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Chemical Structure| 249291-79-0
Chemical Structure| 249291-79-0
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CAS No. :249291-79-0 MDL No. :MFCD09037461
Formula : C6H5ClIN Boiling Point : 260.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :253.47 g/mol Pubchem ID :42553056
Synonyms :

Safety of [ 249291-79-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 249291-79-0 ]

  • Upstream synthesis route of [ 249291-79-0 ]
  • Downstream synthetic route of [ 249291-79-0 ]

[ 249291-79-0 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 75073-11-9 ]
  • [ 249291-79-0 ]
YieldReaction ConditionsOperation in experiment
30% With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 16.5 h; To a stirred solution of concentrated hydrochloride acid (233ml_) at 0°C was added 5-iodo-6-methyl-pyridin-2-ylamine (25 g, 107 mmol, 1 eq) followed by addition of pre-dissolved sodium nitrite (29.5g, 427mmol, 4eq) in water (150ml_) in drop wise manner over period of 30 minutes. Resulting reaction mixture was stirred at room temperature for 16 hours. After complete consumption of starting material, reaction mixture was cooled to 0°C, and pH was adjusted to 12 by saturated aqueous sodium hydroxide solution, extracted with DCM (3x200ml_). Combined organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to get brown oil (20g, crude). Crude was purified by column chromatography using silica gel (100-200 mesh). Desired compound was eluted at 4percent ethyl acetate in hexane to get title compound as brown oil (8g, 30percent). H NMR (400 MHz, CDCI3)8: 2.69 (s, 3H), 6.88 (d, J = 8.04 Hz, 1 H), 7.95 (d, J = 8.24 Hz, 1 H). LC-MS (m/z): 254.0 (M+H).
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 14, p. 2971 - 2973
[2] Patent: WO2014/39484, 2014, A1, . Location in patent: Page/Page column 50; 51
  • 2
  • [ 132606-40-7 ]
  • [ 249291-79-0 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 13, p. 3158 - 3161
  • 3
  • [ 1575836-78-0 ]
  • [ 1233077-33-2 ]
  • [ 249291-79-0 ]
YieldReaction ConditionsOperation in experiment
2.9 g With water; calcium carbonate In 1,4-dioxane for 10 h; Reflux To a stirred solution of 2-bromomethyl-6-chloro-3-iodo-pyridine (20g, crude, 60mmol, 1 eq) in 1 ,4-dioxane (200ml_) was added suspension of CaC03 (31 .4g, 313mmol, 5.2eq) in water (200ml_) at room temperature. Resulting reaction mixture was refluxed for 10 hours. After complete consumption of starting material, reaction mixture was cooled to room temperature and filtered through celite bed over Buchner funnel. Celite bed was washed with EtOAc (2x100ml_). Combined filtrate was washed with water (100ml_) and aqueous sodium bicarbonate (50ml_), dried over sodium sulfate and concentrated under reduced pressure to afford brown solid (21 g, crude). Crude was purified by column chromatography using silica gel (100-200 mesh). Desired compound was eluted at 20percent EtOAc in hexane to get title compound as faint yellow solid (2.9g, 18percent) and also 9g of 6-chloro-3-iodo-2-methyl-pyridine was recovered. H NMR (400 MHz, CDCI3)8: 3.87 (t, J=4.9 Hz, 1 H), 4.63 (d, J = 4.96 Hz, 2H), 7.04 (d, J = 4 Hz, 1 H), 8.0 (d, J = 8.2 Hz, 1 H). LC-MS (m/z): 270.1 (M+H).
Reference: [1] Patent: WO2014/39484, 2014, A1, . Location in patent: Page/Page column 51; 52
  • 4
  • [ 1824-81-3 ]
  • [ 249291-79-0 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 14, p. 2971 - 2973
[2] Patent: WO2014/39484, 2014, A1,
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