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Chemical Structure| 35351-21-4 Chemical Structure| 35351-21-4

Structure of 35351-21-4

Chemical Structure| 35351-21-4

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Product Details of [ 35351-21-4 ]

CAS No. :35351-21-4
Formula : C9H6BrNO2
M.W : 240.05
SMILES Code : NC(=O)C1=CC2=C(O1)C=CC(Br)=C2
MDL No. :MFCD06357123
InChI Key :VYOHEOKELADMTR-UHFFFAOYSA-N
Pubchem ID :2502663

Safety of [ 35351-21-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 35351-21-4 ]

* 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 [ 35351-21-4 ]

[ 35351-21-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 110-85-0 ]
  • t-OBu [ No CAS ]
  • [ 35351-21-4 ]
  • 1-(N,N-dimethylamino)-1'-(dicyclohexylphosphino)biphenyl [ No CAS ]
  • [ 7440-44-0 ]
  • [ 183288-46-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride;Pd(dba)2; In water; ethyl acetate; toluene; EXAMPLE 3 Synthesis of 5-(1-piperazinyl)benzofuran-2-carboxamide from 5-bromobenzofuran-2-carboxamide 0.9 g of 5-bromobenzofuran-2-carboxamide, 0.97 g of piperazine and 2.20 g of Na t-OBu are added to a suspension of 0.06 g of Pd(DBA)2 and 0.07 g of 1-(N,N-dimethylamino)-1'-(dicyclohexylphosphino)biphenyl in 50 ml of toluene, and the mixture is warmed at 120-130 for 16 hours under a protective gas. After cooling, the reaction mixture is added to a mixture of 50 ml of water and 10 ml of 37% hydrochloric acid, 100 ml of ethyl acetate are added, and the mixture is stirred for 20 minutes. A little undissolved product is then removed, and the organic phase is separated off. The aqueous phase is washed again by shaking with 50 ml of ethyl acetate and freed from solvent residues under reduced pressure, clarified using charcoal and filtered. The product is precipitated in crystalline form from the filtrate at 20-22 using 20-25 ml of 32% sodium hydroxide solution.
  • 2
  • P(t-Bu)3 [ No CAS ]
  • t-OBu [ No CAS ]
  • [ 35351-21-4 ]
  • [ 57260-71-6 ]
  • [ 183288-44-0 ]
  • [ 183288-46-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride;Pd(dba)2; In diethylene glycol dimethyl ether; water; 1) Synthesis of 5-(4-tert-butoxycarbonyl-1-piperazinyl)benzofuran-2-carboxamide from 5-bromobenzofuran-2-carboxamide 0.9 g of 5-bromobenzofuran-2-carboxamide, 1.1 g of BOC-piperazine and 1.45 g of Na t-OBu are added to a suspension of 0.06 g of Pd(DBA)2 and 0.25 g of P(t-Bu)3 in 40 ml of diethylene glycol dimethyl ether, and the mixture is warmed at 120-130 C. for 16 hours under a protective gas. After cooling, the mixture is added to water, and the organic phase is diluted with 100 ml of MTBE and washed with 3*50 ml of water. The solvent is evaporated, and the product formed as a solid is filtered off and purified by crystallization from ethanol (product weight: 0.7 g/55%/m.p. 210-213). The subsequent removal of the BOC protecting group using hydrochloric acid and formation of 5-(1-piperazinyl)benzofuran-2-carboxamide, which are shown below only as a reaction equation, can be carried out, for example, as described in GREENE T. W. and WUTS P. G. M., PROTECTIVE GROUPS IN ORGANIC SYNTHESIS.
  • 3
  • [ 110-85-0 ]
  • [ 35351-21-4 ]
  • [ 183288-46-2 ]
YieldReaction ConditionsOperation in experiment
70% With copper(II) cyanide; In N,N-dimethyl-formamide; at 150℃; Example 3 100ml flask was added three 5-bromo-benzofuran-2-carboxamide (4.80g,0.02mol), piperazine (5.16g, 0.06mol), copper cyanide (0.23g, 0.002mol),And dimethylformamide (50ml), was heated with stirring at 150 reaction. The reaction was monitored by thin layer chromatography, the end of the reactionAfter the solvent was removed, 10ml of diethyl ether was added to the system, with vigorous stirring, to precipitate a solid.The solid was recrystallized from ethyl acetate to give 5-piperazinylbenzofuran-2-carboxamide 3.43g, 70% yield.
 

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