Tributylphosphine → 5-chloro-3-(3-chlorobenzyl)-N-[1-(4-cyanophenyl)ethyl]thiophene-2-carboxamide

HRID 870037

反応式

HRID 870037 の反応式
[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

参加物

7

反応物 5

HCID 13831TributylphosphineHCID 15460Diphenyl diselenideHCID 740444'-CyanoacetophenoneHCID 45140204HCID 45140204、化合物HCID 579009824-(1-Azidoethyl)benzonitrile

生成物 1

HCID 579009815-chloro-3-(3-chlorobenzyl)-N-[1-(4-cyanophenyl)ethyl]thiophene-2-carboxamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-27512fc6ee68476f8bc87d3b9152fbd4
出典データセット
uspto-grants-2015_03
特許番号
US08969394B2

関連ノート

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