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[ CAS No. 168317-99-5 ] {[proInfo.proName]}

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Chemical Structure| 168317-99-5
Chemical Structure| 168317-99-5
Structure of 168317-99-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 168317-99-5 ]

CAS No. :168317-99-5 MDL No. :MFCD00684252
Formula : C11H12INO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 301.12 Pubchem ID :-
Synonyms :

Safety of [ 168317-99-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 168317-99-5 ]

* 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 [ 168317-99-5 ]

[ 168317-99-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 123-75-1 ]
  • [ 619-58-9 ]
  • [ 168317-99-5 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 4-iodobenzoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.583333h; Inert atmosphere; Stage #2: pyrrolidine In dichloromethane at 20℃; for 1.25h; Inert atmosphere; 2 A suspension of 4-iodobenzoic acid (8.68 g, 35 mmol) in dichloromethane (120 ml) was treated portionwise over 5 minutes with solid 1,1'-carbonyldiimidazole (5.67 g, 35 mmol) at room temperature with stirring under an atmosphere of argon. This mix was stirred at room temperature for a further 30 minutes. Pyrrolidine (2.49 g, 35 mmol) was then added to the reaction mixture slowly over 15 minutes. The whole mix was then stirred at room temperature under argon for 1 hour. The reaction mix was washed twice with saturated sodium bicarbonate solution (100 ml each), the organic layer was dried over sodium sulphate and the solvent removed under reduced pressure to give the title compound as a brown solid (10.05 g, 95%).1H-NMR (400 MHz, CDCl3) δ: 7.75 (2H, m), 7.26 (2H, m), 3.63 (2H, t, J=7 Hz), 3.40 (2H, m, J=7 Hz), 1.96 (2H, m), 1.88 (2H, m); LC/MS Retention time 2.51 mins/(ES+) 302 (M+H, C11H12INO requires 301).
95% Stage #1: 4-iodobenzoic acid With 1,1'-carbonyldiimidazole In dichloromethane for 0.583333h; Stage #2: pyrrolidine In dichloromethane at 20℃; for 1.25h; 13 Description 13: 1-[(4-iodophenyl)carbonyl]pyrrolidine (D13); A suspension of 4-iodobenzoic acid (8.68g, 35mmol) in dichloromethane (120ml) was treated portionwise over 5 minutes with solid 1 ,1 '-carbonyldiimidazole (5.67g, 35mmol) at room temperature with stirring under an atmosphere of argon. This mixture was stirred at room temperature for a further 30 minutes. Pyrrolidine (2.49g, 35mmol) was then added to the reaction mixture slowly over 15 minutes. The whole mixture was then stirred at room temperature under argon for 1 hour. The reaction mixture was washed twice with saturated sodium bicarbonate solution (100ml each), the organic layer was dried over sodium sulphate and the solvent removed under reduced pressure to give the title compound as a brown solid (10.05g, 95%).1 H-NMR (400MHz, CDCI3) δ: 7.75 (2H, m), 7.26 (2H, m), 3.63 (2H, t, J= 7Hz), 3.40 (2H, m, J=7Hz), 1.96 (2H, m), 1.88 (2H, m); LC/MS Retention time 2.51 mins/(ES+) 302 (M+H, CnH12INO requires 301 ).
88% Stage #1: 4-iodobenzoic acid With thionyl chloride In dichloromethane at 20℃; for 1h; Stage #2: pyrrolidine With triethylamine In dichloromethane at 20℃;
With phenylsilane In toluene at 110℃; for 16h;

  • 2
  • [ 168317-99-5 ]
  • [ 938022-22-1 ]
  • [ 1092459-28-3 ]
YieldReaction ConditionsOperation in experiment
31% With caesium carbonate In dimethyl sulfoxide at 130℃; for 3h; 13 Example 13: 3-(difluoromethyl)-1 -[4-(1 -pyrrolidinylcarbonyl)phenyl]-4,5,6,7- tetrahydro-1H-indazole (E13; A mixture of 3-(difluoromethyl)-4,5,6,7-tetrahydro-1 H-indazole (D15) (0.172g, 0.997mmol), copper (I) oxdide (0.029g, 20mol%), cesium carbonate (0.65Og, 2.0mmol), 1-[(4- iodophenyl)carbonyl]pyrrolidine (D13) (0.30Og, 0.997mmol) and N,N-dimethylglycine (0.103g, 0.997mmol) in DMSO (2ml) was heated under argon at 13O0C for 3 hr. The reaction mixture was diluted with ethyl acetate and filtered through kieselguhr. The filtrate was washed with brine then dried over sodium sulphate. The solvent was removed by rotary evaporation and the desired product was isolated by column chromatography on silica using 10 to 70% ethyl acetate in n-pentane to give the title compound as a white solid (0.107g, 31%). 1 H-NMR (400MHz, CDCI3) δ: 7.63 (2H, m), 7.52 (2H, m), 6.72 (1 H, t, J=54Hz), 3.65 (2H, m), 3.43 (2H, m), 2.72 (4H, app s), 1.98 (2H, m), 1.90 (2H, m), 1.82 (4H, m); LC/MS Retention time 3.02mins/(ES+) 346 (M+H, Ci9H2IF2N3O requires 345).
  • 3
  • [ 168317-99-5 ]
  • [ 1022931-45-8 ]
  • [ 1022930-30-8 ]
YieldReaction ConditionsOperation in experiment
60% With caesium carbonate In dimethyl sulfoxide at 130℃; for 16h; 1 1-[4-(1-pyrrolidinylcarbonyl)phenyl]-3-(trifluoromethyl)-1,4,6,7-tetrahydropyrano[4,3-c]pyrazole A mixture of 1-[(4-iodophenyl)carbonyl]pyrrolidine (D2, 843 mg, 2.80 mmol), 3-(trifluoromethyl)-1,4,6,7-tetrahydropyrano[4,3-c]pyrazole (D4, 563 mg, 2.93 mmol), copper (I) oxide (10 mol %, 0.3 mmol, 43 mg), N,N-dimethylglycine (20 mol %, 0.6 mmol, 62 mg) and cesium carbonate (5.8 mmol, 1.89 g) in dimethylsulfoxide (8 ml) was stirred at 130° C. (oilbath temperature) for 16 h. The reaction mix was cooled and then partitioned between water (30 ml) and dichloromethane (2*20 ml). The organic layers were dried over sodium sulphate and the solvent removed under reduced pressure. The crude product was added to a 20 g isolute pre-packed silica gel sep-pak column and eluted from 0-75% ethyl acetate in petroleum ether. The solvent was removed under reduced pressure to give the title compound as a yellow solid (616 mg, 60%). 1H-NMR (400 MHz, CDCl3) δ: 7.66 (2H, m), 7.58 (2H, m), 4.81 (2H, s), 3.94 (2H, t, J=6 Hz), 3.67 (2H, t, J=7 Hz), 3.44 (2H, t, J=7 Hz), 2.90 (2H, t, J=6 Hz), 2.03-1.88 (4H, m); LC/MS Retention time 2.85 mins/(ES+) 366 (M+H, C18H18F3N3O2requires 365).
60% With copper(I) oxide; dimethylaminoacetic acid; caesium carbonate In dimethyl sulfoxide at 130℃; for 16h;
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