Propyne → 2-isopropoxy-3-methoxy-6-(prop-1-ynyl)-N-trifluoroacetylaniline

HRID 218851

반응식

HRID 218851 반응식
I[C:2]1[C:7]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[C:6]([O:15][CH:16]([CH3:18])[CH3:17])[C:5]([O:19][CH3:20])=[CH:4][CH:3]=1.[CH:21](N(CC)C(C)C)([CH3:23])[CH3:22].C#CC>CN(C=O)C.[Cu]I>[CH:16]([O:15][C:6]1[C:5]([O:19][CH3:20])=[CH:4][CH:3]=[C:2]([C:22]#[C:21][CH3:23])[C:7]=1[NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])([CH3:18])[CH3:17]

참가 물질

6

반응물 3

HCID 6335PropyneHCID 81531DiisopropylethylamineHCID 866376576-iodo-2-isopropoxy-3-methoxy-N-trifluoroacetylaniline

생성물 1

HCID 866376562-isopropoxy-3-methoxy-6-(prop-1-ynyl)-N-trifluoroacetylaniline수율 79%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

A mixture of the product of Step B (0.275 g; 0.681 mmol), Cl2Pd(PPh3)2 (0.058 g; 0.083 mmol); CuI (0.025 g; 0.131 mmol), anhydrous N,N-diisopropyl ethylamine (1 ml) in anhydrous DMF (5 ml) was cooled to −40° C., degassed under reduced pressure and saturated with dry N2. To it, propyne gas (0.5 g; 12.4 mmol) was added at −40° C. The reaction flask was sealed with septum and allowed to warm up to room temperature and stirred overnight at room temperature than evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography (SiO2, hexane/ethyl acetate, 8:2) to give the title compound (0.171 g; 79% yield) as creamy solid. 1H-NMR (CDCl3) 1.21 (d, 6H, J=6.16 Hz); 2.00 (s, 3H); 3.86 (s, 3H); 4.43 (m, 1H, J=6.16 Hz); 6.79 (d, 1H, J=8.67 Hz); 7.14 (d, 1H, J=8.67 Hz); 7.72 (broad s, 1H).

후처리

  1. customdegassed under reduced pressure and saturated with dry N2
  2. customThe reaction flask was sealed with septum
  3. customthan evaporated to dryness under reduced pressure
  4. customThe residue was purified by flash column chromatography (SiO2, hexane/ethyl acetate, 8:2)

출처 및 근거

ORD 기록
ord-ebdc4bdb43cf45098798d6f0795a50f4
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198466B2

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