Diisopropylethylamine → 5-bromo-2-((1S)-2-hydroxy-1-{3-[(trimethylsilyl)ethynyl]benzyl}ethyl)isoindolin-1-one

HRID 339978Notes

Reaction equation

HRID 339978 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([CH2:12]Br)[CH:3]=1.[NH2:14][C@@H:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[C:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:20]=1)[CH2:16][OH:17].C(N(CC)C(C)C)(C)C>C(O)CCC.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:8])[N:14]([C@@H:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[C:26][Si:27]([CH3:29])([CH3:28])[CH3:30])[CH:20]=1)[CH2:16][OH:17])[CH2:12]2

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoateHCID 86681469(2S)-2-amino-3-{3-[(trimethylsilyl)ethynyl]phenyl}propan-1-ol

Product 1

HCID 866814705-bromo-2-((1S)-2-hydroxy-1-{3-[(trimethylsilyl)ethynyl]benzyl}ethyl)isoindolin-1-one

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 4-bromo-2-(bromomethyl)benzoate (0.75 g, 2.4 mmol), (2S)-2-amino-3-{3-[(trimethylsilyl)ethynyl]phenyl}propan-1-ol (0.60 g, 2.4 mmol) and N,N-diisopropylethylamine (2.1 mL, 12 mmol) in 1-butanol (2 mL) in a sealed tube was stirred at 140° C. for 2 h. The solvent was removed under vacuum and the residue was eluted with 0-100% EtOAc in hexanes giving 0.78 g (73% yield) of the pure desired product as off white solid. LC/MS found: 442.0 (M+H)+.

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-5a37da42bcc441bdac4c84f70708c83a
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

Loading…