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

HRID 40118

反応式

HRID 40118 の反応式
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]

参加物

8

反応物 2

HCID 690193-Methylbut-1-yneHCID 112912342-Butyramido-4-nitrophenyl trifluoromethanesulfonate2 回

生成物 1

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

試薬・触媒・溶媒 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 67553Tetrabutylammonium Iodide触媒HCID 178418397HCID 178418397、化合物触媒HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ff17125c20b24a54aa5ad4df529724f2
出典データセット
uspto-grants-2013_09
特許番号
US08524917B2

関連ノート

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