Acetic Anhydride → Acetic acid 2-bromo-6-[6-(1-hydroxy-1-methyl-ethyl)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-benzyl ester

HRID 589513Notes

Reaction equation

HRID 589513 reaction equation
[Br:1][C:2]1[C:3]([CH2:23][OH:24])=[C:4]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]([OH:21])([CH3:20])[CH3:19])[CH:14]=3)[C:9]2=[O:22])[CH:5]=[CH:6][CH:7]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]([OH:21])([CH3:19])[CH3:20])[CH:14]=3)[C:9]2=[O:22])[C:3]=1[CH2:23][O:24][C:25](=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 712310502-(3-Bromo-2-hydroxymethyl-phenyl)-6-(1-hydroxy-1-methyl-ethyl)-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 71231475Acetic acid 2-bromo-6-[6-(1-hydroxy-1-methyl-ethyl)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-benzyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 43 (238 mg, 0.610 mmol) in DCM (6 ml) were added TEA (0.085 ml, 0.610 mmol), DMAP (7.5 mg, 0.061 mmol), and acetic anhydride (62 mg, 0.610 mmol). The resulting mixture was stirred for 24 hrs at r.t. The solvents were removed in vacuo and the crude product was purified by flash chromatography (silica gel, cyclohexane/EtOAC gradient) to yield Intermediate 44.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe crude product was purified by flash chromatography (silica gel, cyclohexane/EtOAC gradient)

Sources & evidence

ORD record
ord-2ef560a778f247268b979f8431e9fb3f
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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