Trimethylsilylacetylene → 5-(2-chloro-6-fluorophenyl)-2-{4-[(trimethylsilyl)ethynyl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 508718노트

반응식

HRID 508718 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:10][C:11](=[O:21])[N:12]([C:14]2[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=2)[N:13]=1.[C:22]([Si:24]([CH3:27])([CH3:26])[CH3:25])#[CH:23]>CS(C)=O.[Cu](I)I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:10][C:11](=[O:21])[N:12]([C:14]2[CH:19]=[CH:18][C:17]([C:23]#[C:22][Si:24]([CH3:27])([CH3:26])[CH3:25])=[CH:16][CH:15]=2)[N:13]=1

참가 물질

6

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 1366448545-(2-chloro-6-fluorophenyl)-2-(4-iodophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

생성물 1

HCID 1366448455-(2-chloro-6-fluorophenyl)-2-{4-[(trimethylsilyl)ethynyl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one수율 107.3%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 5-(2-chloro-6-fluorophenyl)-2-(4-iodophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (0.200 g, 0.483 mmol) in DMSO (2 mL) was added ethynyl(trimethyl)silane (0.071 g, 0.724 mmol), copper iodide (0.005 g, 0.007 mmol), bis(triphenylphosphine) palladium(II) chloride (0.200 g, mmol) and TEA (2.0 mL). The reaction mass was stirred at RT for 24 h. The reaction mass was quenched in water and neutralized with dilute acetic acid and extracted with DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.200 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 2.31 (s, 9H), 7.44-7.47 (m, 3H), 7.54-7.71 (m, 3H), 7.94-8.01 (m, 1H), 77.95 (br s, 1H). MS (m/z): 384.29 (M−H)−.

후처리

  1. customThe reaction mass was quenched in water and neutralized with dilute acetic acid
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bcf8c68f006649b082858bc500081ff7
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096545B2

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