Water → 14-bromo-9-tert-butyl-2-fluoro-3-methoxy-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

HRID 1971760Notes

Reaction equation

HRID 1971760 reaction equation
[C:1]([N:5]1[CH2:26][CH2:25][CH2:24][CH2:23][C:8]2[CH:9]=[C:10]3[C:19]4[CH:18]=[C:17]([F:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:27])([CH3:4])([CH3:3])[CH3:2].[Br:28]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:28][C:9]1[C:8]2[CH2:23][CH2:24][CH2:25][CH2:26][N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6](=[O:27])[C:7]=2[N:11]2[CH2:12][CH2:13][C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([F:20])=[CH:18][C:19]=3[C:10]=12

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 581248809-tert-butyl-2-fluoro-3-methoxy-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

Product 1

HCID 5812491714-bromo-9-tert-butyl-2-fluoro-3-methoxy-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-oneYield 75.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 250 mg 27a in 7 mL dimethylformamide was added 120 mg N-bromosuccinimide. The reaction mixture was stirred at room temperature for 1 h. Water was added and the mixture was extracted with 2×ethyl acetate. The combined organic phases were washed with water and brine, dried and concentrated. The crude product was triturated with heptane/diisopropyl ethyl ether (1:1) to afford 230 mg of 27b as a white solid.

Workup

  1. extractionthe mixture was extracted with 2×ethyl acetate
  2. washThe combined organic phases were washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was triturated with heptane/diisopropyl ethyl ether (1:1)

Sources & evidence

ORD record
ord-7af3003a320142f78f02f59a027dcc6a
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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