Trifluoroacetic acid → HCID 67377153, compound

HRID 877453Notes

Reaction equation

HRID 877453 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[Cl:15])[N:11](C(OC(C)(C)C)=O)[C:10]1[C:9](=[O:23])[CH2:8][CH2:7][CH2:6][C:5]2=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[Cl:15])[NH:11][C:10]1[C:9](=[O:23])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67378172HCID 67378172, compound

Product 1

HCID 67377153HCID 67377153, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 6,7-dichloro-1-oxo-3,4-dihydro-1H-carbazole-9(2H)-carboxylate (1.4 g, 3.9 mmol) in DCM (20 mL), cooled to 0° C., was added TFA (2 mL). The reaction mixture was stirred at 0° C. for 1 h, neutralized with saturated NaHCO3 (15 mL) and extracted with DCM (2×15 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to afford the title compound as a white solid (850 mg, 85%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.87 (bs, 1H), 7.75 (s, 1H), 7.55 (s, 1H), 2.98 (t, J=6.0 Hz, 2H), 2.68 (t, J=6.0 Hz, 2H), 2.30-2.25 (m, 2H).

Workup

  1. extractionextracted with DCM (2×15 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6deeefbcce0c4fdba987402294d2c36e
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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