N-bromobutanimide → 5-Bromo-1-{[(1,1-dimethylethyl)oxy]carbonyl}-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid

HRID 387304Notes

Reaction equation

HRID 387304 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:20])[C:15]=2[C:17]([OH:19])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].C1C(=O)N([Br:28])C(=O)C1>C(Cl)Cl>[Br:28][C:13]1[CH:12]=[C:11]2[C:16](=[C:15]([C:17]([OH:19])=[O:18])[C:14]=1[F:20])[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 593326451h-Indole-1,7-dicarboxylic acid,6-fluoro-2,3-dihydro-,1-(1,1-dimethylethyl)ester

Product 1

HCID 593326855-Bromo-1-{[(1,1-dimethylethyl)oxy]carbonyl}-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acidYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-{[(1,1-dimethylethyl)oxy]carbonyl}-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid (6.9 g, 0.025 mol) in DCM (140 mL) was added NBS (4.8 g, 0.027 mol). The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was washed with water (3×75 mL) and brine (1×75 mL), dried (Na2SO4) and concentrated under reduced pressure, giving 8.3 g (92%) of the title compound.

Workup

  1. washThe reaction mixture was washed with water (3×75 mL) and brine (1×75 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd15c1e34cf9429ba790429639fd417f
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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