Triethylamine → 2-Cyclopropylethynyl-4-fluoro-phenylamine

HRID 2382129노트

반응식

HRID 2382129 반응식
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4](I)[CH:3]=1.[CH:10]1([C:13]#[CH:14])[CH2:12][CH2:11]1.C(N(CC)CC)C>C1COCC1.[Cu]I>[CH:10]1([C:13]#[C:14][NH:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:12][CH2:11]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 138823CyclopropylacetyleneHCID 27782834-Fluoro-2-iodoaniline

생성물 1

HCID 685573712-Cyclopropylethynyl-4-fluoro-phenylamine수율 74.7%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 4-fluoro-2-iodoaniline (2 g, 8.4 mmol) in THF (15 mL) and cyclopropylacetylene (1.4 mL, 16.9 mmol) is treated with PdCl2(PPh3)4 (177 mg, 0.25 mmol), CuI (48 mg, 0.25 mmol) and triethylamine (3.5 mL, 25.2 mmol) and stirred at rt for 2 h. The mixture is filtered through Celite and concentrated. The residue is purified by silica gel chromatography eluting with 0%-35% EtOAc in heptane to afford 2-cyclopropylethynyl-4-fluoro-phenylamine (1.1 g, 74%). MS: 176 (M+H); 1H NMR (300 MHz, CDCl3): δ 6.93 (m, 1H), 6.81 (m, 1H), 6.59 (m, 1H), 4.00 (s, NH2, 2H), 1.49 (m, 1H), 0.82 (m, 4H).

후처리

  1. filtrationThe mixture is filtered through Celite
  2. concentrationconcentrated
  3. customThe residue is purified by silica gel chromatography
  4. washeluting with 0%-35% EtOAc in heptane

출처 및 근거

ORD 기록
ord-7e6b5b5616144dbca57eea1085e34fff
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

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