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Chemical Structure| 856851-34-8 Chemical Structure| 856851-34-8
Chemical Structure| 856851-34-8

3-Iodopyridine-2,6-diamine

CAS No.: 856851-34-8

4.5 *For Research Use Only !

Cat. No.: A861618 Purity: 98%

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Product Details of [ 856851-34-8 ]

CAS No. :856851-34-8
Formula : C5H6IN3
M.W : 235.03
SMILES Code : NC1=NC(N)=CC=C1I
MDL No. :MFCD09032809
InChI Key :JRCCUFRNNYDTGN-UHFFFAOYSA-N
Pubchem ID :476218

Safety of [ 856851-34-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 856851-34-8 ]

* 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.

  • Downstream synthetic route of [ 856851-34-8 ]

[ 856851-34-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 856851-34-8 ]
  • [ 89694-46-2 ]
  • [ 1079401-92-5 ]
YieldReaction ConditionsOperation in experiment
91% With sodium carbonate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In ethanol; water; toluene; at 20℃;Heating / reflux;Product distribution / selectivity; To 3-iodopyridine-2,6-diamine (Preparation 44, 3.0 g, 12.8 mmol), 5-methoxy-2- chlorophenylboronic acid (2.62 g, 14.0 mmol), sodium carbonate (1.49 g, 14.0 mmol), ethanol (15 ml), water (15 ml) and tris(dibenzylideneacetone)dipalladium (0) (175 mg,0.19 mmol) at ambient temperature under a nitrogen atmosphere was added tri- <n="142"/>terfbutylphosphine (1M in toluene, 0.574 ml, 0.574 mmol). The brown mixture was heated to reflux and maintained until reaction completion by HPLC. The reaction was cooled to ambient and the ethanol removed by vacuum distillation. 2- methyltetrahydrofuran (30 ml) was then added and the biphasic mixture filtered over arbocel.(TM)., extracted with saturated aqueous sodiumhydrogencarbonate (20 ml) and separated. The organic layer was extracted five times with 10percent w/v citric acid (20 ml), then to the combined aqueous layers was added 2-methyltetrahydrofuran (30 ml) then 5M sodium hydroxide until obtaining a pH>10. The layers were separated and the upper organic layer was concentrated to dryness in vacuo obtaining product as a beige solid 2.90 g (91percent yield).
55% With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 80℃; for 19h;Product distribution / selectivity; To a suspension of 3-iodopyridine-2,6-diamine (Preparation 44, 2 g, 8.51 mmol) in 1 ,4- dioxane (10 ml) and water (5 ml) was added <strong>[89694-46-2]2-chloro-5-methoxyphenyl boronic acid</strong> (0.793 g, 4.25 mmol), cesium carbonate (2.77 g, 8.51 mmol) and palladium tetrakis(triphenylphosphine) (0.123 g, 0.0125 mmol). The reaction was purged with nitrogen and heated at 80QC for 20 minutes. Three further portions of palladium tetrakis(triphenylphosphine) (0.123 g, 0.0125 mmol) and <strong>[89694-46-2]2-chloro-5-methoxyphenyl boronic acid</strong> (0.793 g, 4.25 mmol) were added at 20 minute intervals. The reaction was heated at 8O0C for 18 hours before concentrating in vacuo. The residue was taken up in ethyl acetate (20 ml) and washed with a saturated aqueous solution of brine (20 ml) before drying over Na2SO4 and concentrating in vacuo. The residue was purified by silica gel column chromatography, eluting with 50:50 to 100:0 ethyl acetate-.pentane to afford the title compound as a brown foam (1.157 g, 55percent yield). MS m/z 250 [MH]+1HNMR (CDCI3): 3.79 (s, 3H), 4.23 (br s, 2H), 4.32 (br s, 2H), 6.00 (d, 1 H), 6.86 (m,2H), 7.14 (d, 1 H), 7.38 (d, 1 H)
 

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