Bromide ion → Methyl isoindoline-5-carboxylate

HRID 582693Notes

Reaction equation

HRID 582693 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].C[C@@H:9](NC(=O)O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[Br-].[CH3:22]CN(CC)CC>C1(C)C=CC=CC=1>[CH3:22][O:5][C:3]([C:2]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH2:13][NH:12][CH2:11]2)=[O:4]

Participants

5

Reactant 3

HCID 259Bromide ionHCID 8471TriethylamineHCID 86754265[1(R) Methyl-2-(pyridin-2-yl)ethyl]carbamic acid trifluoroacetate

Product 1

HCID 19828496Methyl isoindoline-5-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A toluene solution (20 mL) of 7-4 (181 mg, 0.48 mmol), 2-5 (171 mg, 0.60 mmol) and Et3N (266 μl, 1.9 mmol) was refluxed for 3 h and then concentrated to dryness. The residue was purified by flash chromatography (silica, 3:2 CH2Cl2 /acetone) to provide 7-5 as a colorless gum.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was purified by flash chromatography (silica, 3:2 CH2Cl2 /acetone)

Sources & evidence

ORD record
ord-e6c91ffca3d442c29f884fd1052fe7ec
Source dataset
uspto-grants-1999_07
Patent number
US05925655

Reaction notes

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