Trifluoroacetic acid → HCID 67377772, compound

HRID 877470Notes

Reaction equation

HRID 877470 reaction equation
[Cl:1][C:2]1[C:14]([F: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(Cl)Cl>[Cl:1][C:2]1[C:14]([F: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

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67377902HCID 67377902, compound

Product 1

HCID 67377772HCID 67377772, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 5-chloro-6-fluoro-1-oxo-3,4-dihydro-1H-carbazole-9(2H)-carboxylate (0.4 g, 1.1 mmol) in DCM (10 mL), cooled to 0° C., was added TFA (1 mL). The reaction mixture was stirred at room temperature for 4 h, quenched with saturated NaHCO3 (pH-8) and then extracted with DCM (4×40 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude compound which was washed with hexane (2×5 mL) to provide the title compound (0.20 g, 71%). 1H NMR (200 MHz, DMSO-d6, δ in ppm) 12.04 (bs, 1H), 7.41-7.26 (m, 2H), 3.33 (t, J=6.0 Hz, 2H), 2.60 (t, J=5.8 Hz, 2H), 2.22-2.13 (m, 2H).

Workup

  1. customquenched with saturated NaHCO3 (pH-8)
  2. extractionextracted with DCM (4×40 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude compound which
  6. washwas washed with hexane (2×5 mL)

Sources & evidence

ORD record
ord-a22967bc7c4048409961ef05c5f8203a
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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