N-methoxy-N-methyl-2-(thiophen-2-yl)acetamide → 1-[4-(1-Azido-1-methylethyl)phenyl]-2-(2-thienyl)ethanone

HRID 732872Notes

Reaction equation

HRID 732872 reaction equation
[Li]CCCC.[N:6]([C:9]([C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1)([CH3:11])[CH3:10])=[N+:7]=[N-:8].CON(C)[C:22](=[O:29])[CH2:23][C:24]1[S:25][CH:26]=[CH:27][CH:28]=1>C1COCC1>[N:6]([C:9]([C:12]1[CH:17]=[CH:16][C:15]([C:22](=[O:29])[CH2:23][C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[CH:14][CH:13]=1)([CH3:11])[CH3:10])=[N+:7]=[N-:8]

Participants

5

Reactant 3

HCID 15029898N-methoxy-N-methyl-2-(thiophen-2-yl)acetamideHCID 538389621-(1-Azido-1-methylethyl)-4-bromobenzeneHCID 178418339Butyllithium

Product 1

HCID 866174631-[4-(1-Azido-1-methylethyl)phenyl]-2-(2-thienyl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

nBuLi (1.6M in hexane, 2.88 mL, 4.60 mmol) was added dropwise to a solution of 1-(1-azido-1-methylethyl)-4-bromobenzene (2-3, 1.03 g, 4.28 mmol) in THF (20 mL) at −78° C. After 15 min a solution of N-methoxy-N-methyl-2-thien-2-ylacetamide (1-1, 0.78 g, 4.18 mmol) in THF (1 mL) was added. After an additional 30 min at −78° C., the reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate, dried over magnesium sulfate, filtered, and concentrated to give an oil. The crude product was purified via automated flash column chromatography on silica gel (5% CH2Cl2, 0-10% EtOAc/hexanes over 30 min) to give the title compounds as a yellow oil. LRMS m/z (M+1) Calcd: 286.1,. Found 286.2.

Workup

  1. customthe reaction was quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe crude product was purified via automated flash column chromatography on silica gel (5% CH2Cl2, 0-10% EtOAc/hexanes over 30 min)

Sources & evidence

ORD record
ord-a3f13adaa5db48cdb95bb1e17ae7bac1
Source dataset
uspto-grants-2009_09
Patent number
US07589068B2

Reaction notes

Loading…