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

HRID 1837728ノート

反応式

HRID 1837728 の反応式
[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

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 22678449HCID 22678449、化合物HCID 22678484HCID 22678484、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c4baefde84a34653b2486c277d617a37
出典データセット
uspto-grants-2004_08
特許番号
US06784192B2

反応ノート

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