Trifluoroacetic acid → HCID 68264844, compound

HRID 877499Notes

Reaction equation

HRID 877499 reaction equation
[Cl:1][C:2]1[C:3]([Cl:22])=[CH:4][C:5]2[C:6]3[CH2:20][CH2:19][C:18](=[O:21])[C:7]=3[N:8](C(OC(C)(C)C)=O)[C:9]=2[CH:10]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([Cl:22])=[CH:4][C:5]2[C:6]3[CH2:20][CH2:19][C:18](=[O:21])[C:7]=3[NH:8][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67377961HCID 67377961, compound

Product 1

HCID 68264844HCID 68264844, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 6,7-dichloro-3-oxo-2,3-dihydrocyclopenta[b]indole-4(1H)-carboxylate (0.34 g, 1.0 mmol) in CH2Cl2 (10 mL), cooled to 0° C., TFA (1 mL) was added. The reaction mixture was slowly warmed to room temperature and stirred for 90 min., quenched with saturated NaHCO3 (pH-8) and extracted with DCM (3×100 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude compound which was purified by washing with 5% EtOAc-hexane (3×20 mL) to provide the title compound (200 mg, 83%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 11.96 (s, 1H), 8.06 (s, 1H), 7.65 (s, 1H), 3.03 (t, J=3.5 Hz, 2H), 2.92 (t, J=4.0 Hz, 2H).

Workup

  1. customquenched with saturated NaHCO3 (pH-8)
  2. extractionextracted with DCM (3×100 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude compound which
  6. customwas purified
  7. washby washing with 5% EtOAc-hexane (3×20 mL)

Sources & evidence

ORD record
ord-f48d032748934bce977c83dd97c8520b
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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