Trifluoroacetic acid → 5-bromo-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid

HRID 387305Notes

Reaction equation

HRID 387305 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([OH:14])=[O:13])[C:10]=1[F:11])[N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([OH:14])=[O:13])[C:10]=1[F:11])[NH:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593326855-Bromo-1-{[(1,1-dimethylethyl)oxy]carbonyl}-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid

Product 1

HCID 593326645-bromo-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acidYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-bromo-1-{[(1,1-dimethylethyl)oxy]carbonyl}-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid (8.3 g, 0.023 mol) in DCM (90 mL) was added TFA (90 mL). The reaction mixture was stirred at room temperature for 3 h and then concentrated. The residue was partitioned between EtOAc (100 mL) and water (100 mL), and the aqueous fraction was extracted with EtOAc (2×50 mL). The combined organic layers were washed with water (1×50 mL) and brine (1×50 mL). dried (Na2SO4) and concentrated under reduced pressure, giving 5.9 g (99%) of the title compound.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between EtOAc (100 mL) and water (100 mL)
  3. extractionthe aqueous fraction was extracted with EtOAc (2×50 mL)
  4. washThe combined organic layers were washed with water (1×50 mL) and brine (1×50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-421d0cf76e084f3b920c6d662d02169f
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

Loading…