Dimethylformamide → 1-[(2-Methoxy-3-pyridyl)methyl]-4-[2-[3-(methylsulfonyl)-2-thienyl]-1-ethynyl]piperidine

HRID 1837728노트

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HRID 1837728 반응식
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([C:16]#[CH:17])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.Br[C:19]1[S:20][CH:21]=[CH:22][C:23]=1[S:24]([CH3:27])(=[O:26])=[O:25].C(N(CC)CC)C.CN(C)C=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([C:16]#[C:17][C:19]3[S:20][CH:21]=[CH:22][C:23]=3[S:24]([CH3:27])(=[O:26])=[O:25])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 22678449HCID 22678449, 화합물HCID 22678484HCID 22678484, 화합물

생성물 1

HCID 226783641-[(2-Methoxy-3-pyridyl)methyl]-4-[2-[3-(methylsulfonyl)-2-thienyl]-1-ethynyl]piperidine수율 53.1%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

500 mg of 1-[(2-methoxy-3-pyridyl)methyl]-4-(1-ethynyl)piperidine, 530 mg of 2-bromo-3-(methylsulfonyl)thiophene, 21 mg of anhydrous cupric iodide and 127 mg of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent of 2.2 ml of triethylamine and 2.2 ml of N,N-dimethylformamide, and the mixture was stirred at 100° C. for 2 hours under nitrogen flow. Ethyl acetate was added to the reaction solution, and the resulting precipitates were filtered off. Then, water was added to the filtrate, and the mixture was extracted with ethyl acetate. The solvent was evaporated, and then the crude product was purified by silica gel column chromatography (ethyl acetate), to give 450 mg of the title compound as a colorless oil.

후처리

  1. customthe resulting precipitates
  2. filtrationwere filtered off
  3. additionThen, water was added to the filtrate
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe solvent was evaporated
  6. customthe crude product was purified by silica gel column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-c4baefde84a34653b2486c277d617a37
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06784192B2

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