Tributylphosphine → 5-Chloro-3-[(3-chlorophenyl)methyl]-N-[1-(4-cyanophenyl)ethyl]-2-thiophenecarboxamide

HRID 870037

Reaction equation

HRID 870037 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[C:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[CH:3]=1.[N:18]([CH:21]([C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1)[CH3:22])=[N+]=[N-].C(C1C=CC(C#N)=CC=1)(=O)C.C1([Se][Se]C2C=CC=CC=2)C=CC=CC=1.C(P(CCCC)CCCC)CCC>C(#N)C>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:18][CH:21]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[CH3:22])=[O:9])=[C:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[CH:3]=1

Participants

7

Reactant 5

HCID 13831TributylphosphineHCID 15460Diphenyl diselenideHCID 740444'-CyanoacetophenoneHCID 45140204HCID 45140204, compoundHCID 57900982HCID 57900982, compound

Product 1

HCID 579009815-Chloro-3-[(3-chlorophenyl)methyl]-N-[1-(4-cyanophenyl)ethyl]-2-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 5-chloro-3-(3-chlorobenzyl)thiopbene-2-carboxylic acid from Example 1, Step 6 (230 mg, 0.801 mmol), 4-(1-azidoethyl)benzonitrile (146 mg, 0.848 mmol) [prepared according to Thompson et al. J. Org. Chem. 1993, 58, 5886, after reduction of commercially available 4-acetylbenzonitrile] and diphenyl diselenide (549 mg, 1.76 mmol) in acetonitrile at r.t. under N2 was added tributylphosphine (217 μL, 0.881 mmol, 1.1 eq) dropwise (suspension dissolved, slightly exothermic) and the mixture was stirred at r.t. for 6 h, quenched with saturated NaHCO3 and extracted with ether. The crude was purified by Combi Flash chromatography system (10-40% EtOAc/hexane) to give the desired product.

Workup

  1. customprepared
  2. dissolutiondissolved
  3. customquenched with saturated NaHCO3
  4. extractionextracted with ether
  5. customThe crude was purified by Combi Flash chromatography system (10-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-27512fc6ee68476f8bc87d3b9152fbd4
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Linked notes

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