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

HRID 870037

반응식

HRID 870037 반응식
[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

참가 물질

7

반응물 5

HCID 13831TributylphosphineHCID 15460Diphenyl diselenideHCID 740444'-CyanoacetophenoneHCID 45140204HCID 45140204, 화합물HCID 57900982HCID 57900982, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-27512fc6ee68476f8bc87d3b9152fbd4
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969394B2

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