Triethylamine → 3-Chloro-5-(4-fluoro-3-methylphenylethynyl)-pyridine

HRID 606888

反応式

HRID 606888 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([CH3:10])[CH:4]=1)#[CH:2].C(N(CC)CC)C.[Cl:18][C:19]1[CH:20]=[C:21](OS(C(F)(F)F)(=O)=O)[CH:22]=[N:23][CH:24]=1>C(OCC)(=O)C.[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:18][C:19]1[CH:24]=[N:23][CH:22]=[C:21]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][C:6]([F:9])=[C:5]([CH3:10])[CH:4]=2)[CH:20]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 151858705-Chloropyridin-3-yl trifluoromethanesulfonateHCID 162137974-Ethynyl-1-fluoro-2-methylbenzene

生成物 1

HCID 670478013-Chloro-5-(4-fluoro-3-methylphenylethynyl)-pyridine収率 44%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178419050HCID 178419050、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

Add 4-ethynyl-1-fluoro-2-methylbenzene (0.56 g, 4.21 mmol), triethylamine (2.2 mL, 15 mmol), copper (I) iodide (36 mg, 0.19 mmol), and bis(triphenylphosphine)palladium (II) dichloride (110 mg, 0.15 mmol) to a solution of trifluoromethanesulfonic acid 5-chloropyridin-3-yl ester, (prepared as described in PREPARATION 25), (1.0 g, 3.8 mmol) in ethyl acetate (5 mL) under nitrogen. Heat the at 70° C. for 16 h and concentrate. Purify by silica gel chromatography, eluting with 100% dichloromethane, followed by a second silica gel chromatography eluting with 50:50 to 60:40 dichloromethane:hexanes, to give the title compound as a light yellow solid (410 mg, 44%).

後処理

  1. concentrationconcentrate
  2. customPurify by silica gel chromatography
  3. washeluting with 100% dichloromethane
  4. washeluting with 50:50 to 60:40 dichloromethane

出典と根拠

ORDレコード
ord-111deb5bc23f43d6822ed2d4aef65921
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

関連ノート

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