Dichloromethane → Tert-butyl 1-(4-((4-ethoxyphenyl)ethynyl)phenyl)propan-2-yl-carbamate

HRID 76168

반응식

HRID 76168 반응식
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]#[CH:29])=[CH:24][CH:23]=1)[CH3:20].ClCCl>C(#N)C.[Cu]I>[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:29]#[C:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][CH2:19][CH3:20])=[CH:23][CH:24]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 27751241-Ethoxy-4-ethynylbenzeneHCID 15576539[2-(4-Iodo-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester

생성물 1

HCID 66611490Tert-butyl 1-(4-((4-ethoxyphenyl)ethynyl)phenyl)propan-2-yl-carbamate

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6342Acetonitrile용매

실험 절차

To 5.00 g (13.8 mmol) [2-(4-iodo-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (I52.5) and 2.02 g (13.8 mmol) 4-ethoxyphenylacetylene in 80 mL ACN are added 4.46 mL (32.2 mmol) TEA, 135.6 mg (0.17 mmol) [1,1′-bis(diphenyl-phosphino)ferrocene]dichloropalladium(II) complex with dichloromethane and 32.3 mg (0.17 mmol) CuI, and the reaction mixture is stirred at r.t. over night. The precipitate is filtered and washed with ACN. The resulting crude product is purified by column chromatography (CyH/EtOAc 100/0→90/10).

후처리

  1. filtrationThe precipitate is filtered
  2. washwashed with ACN
  3. customThe resulting crude product is purified by column chromatography (CyH/EtOAc 100/0→90/10)

출처 및 근거

ORD 기록
ord-267c18524a75466daf6e51e2fb4d4337
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835472B2

연결된 노트

불러오는 중…