Triethylamine → (4-Bromo-2-phenylethynyl-thiazol-5-yl)-piperidin-1-yl-methanone

HRID 2092969ノート

反応式

HRID 2092969 の反応式
Br[C:2]1[S:3][C:4]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])=[C:5]([Br:7])[N:6]=1.[C:16]1([C:22]#[CH:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Br:7][C:5]1[N:6]=[C:2]([C:23]#[C:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:3][C:4]=1[C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:9]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 58227559(2,4-Dibromo-thiazol-5-yl)-piperidin-1-yl-methanone

生成物 1

HCID 58227508(4-Bromo-2-phenylethynyl-thiazol-5-yl)-piperidin-1-yl-methanone収率 20%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒

反応条件

温度
90 °C

実験手順

To a stirred solution of a mixture of intermediate 49 (2,4-Dibromo-thiazol-5-yl)-piperidin-1-yl-methanone (325 mg, 0.918 mmol), bis(triphenylphosphine)palladium(II) chloride (12.9 mg, 0.0184 mmol), copper(I) iodide (8.74 mg, 0.0459 mmol) and phenylacetylene (0.101 mL, 0.918 mmol) was added triethylamine (3.0 mL, 22 mmol) and the reaction was heated at 90° C. for 30 minutes in a microwave (150 watts). The solvent triethylamine was removed and the crude product was extracted with dichloromethane and washed the organic portion with aqueous citric acid solution, water and brine. Purification of the crude product afford the titled compound (4-Bromo-2-phenylethynyl-thiazol-5-yl)-piperidin-1-yl-methanone (60 mg, 20%) as a pale brown color solid

後処理

  1. customThe solvent triethylamine was removed
  2. extractionthe crude product was extracted with dichloromethane
  3. washwashed the organic portion with aqueous citric acid solution, water and brine
  4. customPurification of the crude product

出典と根拠

ORDレコード
ord-d8e38c0e5a4f490b8b10118b77ebb566
出典データセット
uspto-grants-2013_05
特許番号
US08440837B2

反応ノート

読み込み中…