Aniline → HCID 59401152, compound

HRID 77062Notes

Reaction equation

HRID 77062 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4](OS(C)(=O)=O)[C:5]1[S:6][C:7]([CH3:10])=[CH:8][CH:9]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(C(C)C)C(C)C)C>CC#N>[CH3:1][O:2][C:3](=[O:16])[CH:4]([C:5]1[S:6][C:7]([CH3:10])=[CH:8][CH:9]=1)[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 59401155HCID 59401155, compound

Product 1

HCID 59401152HCID 59401152, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methanesulfonyloxy-(5-methyl-thiophen-2-yl)-acetic acid methyl ester (I266) (2.10 g, 7.94 mmol), aniline (1.09 mL, 11.9 mmol) and N-ethyl-N-isopropylpropan-2-amine (2.04 mL, 11.9 mmol) in MeCN (10 mL) is heated under microwave irradiation at 100° C. for 1 hour. The solvent is removed, DCM is added and the organic phase is washed with water and brine, dried over Na2SO4 and evaporated. The resulting brown oil is purified by silica gel flash chromatography (Hexane/EtOAc=9575 to 90/10) to obtain intermediate I269 as a yellow oil (500 mg, 24% yield).

Workup

  1. customThe solvent is removed
  2. additionDCM is added
  3. washthe organic phase is washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe resulting brown oil is purified by silica gel flash chromatography (Hexane/EtOAc=9575 to 90/10)

Sources & evidence

ORD record
ord-8b2f1027c7f24140b7db155932865551
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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