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

HRID 2092969노트

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HRID 2092969 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매

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온도
90 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-d8e38c0e5a4f490b8b10118b77ebb566
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440837B2

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