Triethylamine → 3-Fluoro-5-phenylethynylpyridine

HRID 606844ノート

反応式

HRID 606844 の反応式
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:16][C:17]1[CH:18]=[C:19](OS(C(F)(F)F)(=O)=O)[CH:20]=[N:21][CH:22]=1>C(OCC)(=O)C.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>[F:16][C:17]1[CH:22]=[N:21][CH:20]=[C:19]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:18]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 11413882Methanesulfonic acid, trifluoro-, 5-fluoro-3-pyridinyl ester

生成物 1

HCID 670474963-Fluoro-5-phenylethynylpyridine収率 65%

試薬・触媒・溶媒 2

HCID 178419050HCID 178419050、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

Add phenylacetylene (0.180 mL, 1.6 mmol), copper (I) iodide (0.015 g, 0.08 mmol) bis(triphenylphosphine)palladium (II) dichloride (0.027 g. 0.04 mmol) and triethylamine (0.85 mL, 6 mmol) to a solution of trifluoromethanesulfonic acid 5-fluoro-pyridin-3-yl ester, (prepared essentially as described in PREPARATION 6), (0.367 g, 1.5 mmol) in degassed ethyl acetate (1.5 mL) and heat at 60° C. for 16 h. Cool the reaction mixture to room temperature, filter through diatomaceous earth, wash with ethyl acetate, and concentrate. Purify the residue by silica gel chromatography, eluting with dichloromethane, to give the title compound (0.192 g, 65%).

後処理

  1. custom(prepared essentially
  2. temperatureCool the reaction mixture to room temperature
  3. filtrationfilter through diatomaceous earth
  4. washwash with ethyl acetate
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-55c22a639733475fa7dc8b4eaaabb4ef
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

反応ノート

読み込み中…