Trifluoroacetic acid → HCID 67377640, compound

HRID 877460Notes

Reaction equation

HRID 877460 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][C:8](=[O:23])[C:9]=1[N:10]2C(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][C:8](=[O:23])[C:9]=1[NH:10]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67378293HCID 67378293, compound2×

Product 1

HCID 67377640HCID 67377640, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 5,6-dichloro-1-oxo-3,4-dihydro-1H-carbazole-9(2H)-carboxylate (intermediate 1b) (0.9 g, 2.5 mmol) was dissolved in DCM (15 mL), cooled to 0° C., and TFA (1.6 mL) was added. The reaction mixture was stirred at 0° C. for 1 h, neutralized with saturated NaHCO3 (20 mL) and extracted with DCM (2×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the title compound as a white solid (450 mg, 70%) which was directly in the next step without further purification. 1H NMR (500 MHz, CDCl3, δ in ppm) 9.18 (bs, 1H), 7.38 (d, J=9.0 Hz, 1H), 7.28 (d, J=9.5 Hz, 1H), 3.37 (t, J=6.0 Hz, 2H), 2.67 (t, J=7.0 Hz, 2H), 2.30-2.25 (m, 2H).

Workup

  1. extractionextracted with DCM (2×20 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9d80199269a44488ae7536a441b161d
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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