Trifluoroacetic acid → HCID 67377734, compound

HRID 877473Notes

Reaction equation

HRID 877473 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH2:7][CH2:8][CH2:9][C:10](=[O:22])[C:11]=3[N:12]2C(OC(C)(C)C)=O)=[CH:4][C:3]=1[F:23].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH2:7][CH2:8][CH2:9][C:10](=[O:22])[C:11]=3[NH:12]2)=[CH:4][C:3]=1[F:23]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67377888HCID 67377888, compound

Product 1

HCID 67377734HCID 67377734, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 7-chloro-6-fluoro-1-oxo-3,4-dihydro-1H-carbazole-9(2H)-carboxylate (0.55 g, 1.6 mmol) was dissolved in DCM (10 mL), cooled to 0° C., and TFA (1 mL) was added slowly. The reaction mixture was brought to room temperature and stirred for 5 h, neutralized with saturated NaHCO3 (10 mL) and extracted with DCM (3×10 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to obtain the title compound (0.35 mg, 92%) which was used in the next step with out any purification. 1H NMR (200 MHz, DMSO-d6, δ in ppm) 11.84 (bs, 1H), 7.76 (d, J=9.8 Hz, 1H), 7.52 (d, J=6.2 Hz, 1H), 2.95 (t, J=6.0 Hz, 2H), 2.60 (t, J=5.8 Hz, 2H), 2.20 (m, 2H).

Workup

  1. customwas brought to room temperature
  2. extractionextracted with DCM (3×10 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da3e03bd414347cf97895452acec1df2
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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