Ethanolamine → 8-Bromo-9b-phenyl-2,3-dihydro-9bH-oxazolo[2,3-a]isoindol-5-one

HRID 513228Notes

Reaction equation

HRID 513228 reaction equation
[C:1]([C:9]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]([N:22](CC)C(C)C)(C)[CH3:20].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(CN)O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C=O>[Br:18][C:16]1[CH:17]=[C:9]2[C:10]([C:11](=[O:13])[N:22]3[CH2:19][CH2:20][O:8][C:1]32[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 3467342-Benzoyl-4-bromobenzoic acidHCID 521998p-Toluenesulfonic acid monohydrateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 1175994958-Bromo-9b-phenyl-2,3-dihydro-9bH-oxazolo[2,3-a]isoindol-5-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-Benzoyl-4-bromo-benzoic acid (100 mg; 0.33 mmol) in N,N-dimethylformamide (1 ml) with N,N-Diisopropylethylamine (127 μl; 0.98 mmol) is added HATU (137 mg; 0.36 mmol). It is stirred at ambient temperature for 5 minutes before ethanolamine (21 μl; 0.33 mmol) is added. After 4 hours the reaction mixture is purified via reversed phase chromatography under basic conditions. The received 5-Bromo-3-hydroxy-2-(2-hydroxy-ethyl)-3-phenyl-2,3-dihydro-isoindol-1-one is taken up in 1 ml toluene and treated with p-Toluenesulfonic acid monohydrate (3 mg; 0.02 mmol) at 120° C. for 2 days. It is purified via reversed phase chromatography under basic conditions.

Workup

  1. additionis added
  2. customAfter 4 hours the reaction mixture is purified via reversed phase chromatography under basic conditions
  3. customIt is purified via reversed phase chromatography under basic conditions

Sources & evidence

ORD record
ord-dc1c351384d74a349b3f016a161a9887
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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