3-Methylbut-1-yne → N-(2-(3-Methylbut-1-ynyl)-5-nitrophenyl)butyramide

HRID 40118

반응식

HRID 40118 반응식
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[NH:16][C:17](=[O:21])[CH2:18][CH2:19][CH3:20])(=O)=O.[CH3:24][CH:25]([CH3:28])[C:26]#[CH:27]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CC#N.CCN(CC)CC.[Cu]I.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>[CH3:24][CH:25]([CH3:28])[C:26]#[C:27][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[NH:16][C:17](=[O:21])[CH2:18][CH2:19][CH3:20]

참가 물질

8

반응물 2

HCID 690193-Methylbut-1-yneHCID 112912342-Butyramido-4-nitrophenyl trifluoromethanesulfonate2회

생성물 1

HCID 59762443N-(2-(3-Methylbut-1-ynyl)-5-nitrophenyl)butyramide

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 67553Tetrabutylammonium Iodide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

반응 조건

온도
0 °C

실험 절차

A mixture of 2-butyramido-4-nitrophenyl trifluoromethanesulfonate (Compound 118, 200 mg, 0.56 mmol), CuI (32 mg, 0.17 mmol), and n-Bu4NI (311 mg, 0.84 mmol) in CH3CN (5 ml) and Et3N (1 ml) was purged with N2 for 10 min and Pd(PPh3)4 (64 mg, 0.056 mmol) was added and the mixture was purged with N2 for another 5 min. The mixture was then cooled to 0° C. and 3-methyl-1-butyne (76 mg, 1.12 mmol) was added. After 5 min, the reaction was quenched with aqueous NaHCO3, extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes) to yield the title compound.

후처리

  1. customwas purged with N2 for 10 min
  2. customthe mixture was purged with N2 for another 5 min
  3. customthe reaction was quenched with aqueous NaHCO3
  4. extractionextracted with EtOAc (×3)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel (0→20% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-ff17125c20b24a54aa5ad4df529724f2
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524917B2

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