Triethylamine → 2-Cyclopropylethynyl-4-fluoro-phenylamine

HRID 2382129ノート

反応式

HRID 2382129 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 685573712-Cyclopropylethynyl-4-fluoro-phenylamine収率 74.7%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7e6b5b5616144dbca57eea1085e34fff
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

反応ノート

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