Stannous Chloride → Benzamide

HRID 2092510Notes

Reaction equation

HRID 2092510 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+]([O-])=O)[C:5](O)=[O:6].CC[N:16]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.Cl[Sn]Cl>CCO.CN(C=O)C>[C:5]([NH2:16])(=[O:6])[C:4]1[CH:8]=[CH:9][CH:10]=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 24479Stannous ChlorideHCID 757711-HydroxybenzotriazoleHCID 2306533-Fluoro-4-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

In one embodiment, intermediate [1C] is prepared according to Scheme 5A. In this route, 3-fluoro-4-nitro benzoic acid [Q1] is converted to corresponding amide [R1] using R7R8NH, EDCI.HCl, HOBt, TEA, and DMF at about rt for about 10 h. Amide [R1] is then reduced using SnCl2 in EtOH at reflux for about 3-4 h to provide benzamide [S1]. Benzamide [S1] is then converted to urea [T1] using 4-bromophenylisocyanate in the presence of TEA and DCM at about rt. Conversion of urea [T1] to intermediate [1C] is accomplished using Pd(dppf)Cl2.DCM, bis(pinacolato)diboron, KOAc, and 1,4-dioxane, at about 110° C. for about 10 h.

Workup

  1. customat about rt
  2. customfor about 10 h
  3. temperatureat reflux for about 3-4 h

Sources & evidence

ORD record
ord-bcd9e151ef144edebbb2bd10a53e5f8e
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Reaction notes

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