Methyl 2-(2,2-dimethylpropionylamino)-6-(prop-2-ynyloxy)benzoate → Methyl 7-pivalamido-2H-chromene-8-carboxylate

HRID 2200343Notes

Reaction equation

HRID 2200343 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]#[CH:19])[C:7]=1[C:8]([O:10][CH3:11])=[O:9])=[O:4]>C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([NH:5][C:6]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:12]2[C:13]([CH:19]=[CH:18][CH2:17][O:16]2)=[CH:14][CH:15]=1)=[O:4]

Participants

3

Reactant 1

HCID 86713295Methyl 2-(2,2-dimethylpropionylamino)-6-(prop-2-ynyloxy)benzoate2×

Product 1

HCID 70983794Methyl 7-pivalamido-2H-chromene-8-carboxylateYield 75.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of methyl 2-(2,2-dimethylpropionylamino)-6-(prop-2-ynyloxy)benzoate (Intermediate 13, 4.74 g) and [bis(trifluoromethanesulfonyl)imidate]-(triphenylphosphine)gold (2:1) toluene adduct (0.060 g) in toluene (70 mL) was heated to 85° C., under an atmosphere of nitrogen for 3 hours. After cooling, the mixture was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 0-20% to give methyl 7-(2,2-dimethylpropionylamino)-2H-chromene-8-carboxylate (3.59 g) as a colourless oil.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. customthe residue was purified by chromatography on silica
  4. washeluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 0-20%

Sources & evidence

ORD record
ord-05ee77815a244ffe8d1412218eeafaaf
Source dataset
uspto-grants-2016_06
Patent number
US09359369B2

Reaction notes

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