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

HRID 40118

Reaction equation

HRID 40118 reaction equation
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]

Participants

8

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 67553Tetrabutylammonium IodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-ff17125c20b24a54aa5ad4df529724f2
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Linked notes

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