Trifluoroacetic acid → HCID 71253222, compound

HRID 877504Notes

Reaction equation

HRID 877504 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](C(OC(C)(C)C)=O)[C:6]3[C:18](=[O:21])[CH2:19][CH2:20][C:5]=3[C:4]=2[C:3]=1[Cl:22].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:18](=[O:21])[CH2:19][CH2:20][C:5]=3[C:4]=2[C:3]=1[Cl:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67378066HCID 67378066, compound2×

Product 1

HCID 71253222HCID 71253222, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 7,8-dichloro-3-oxo-2,3-dihydrocyclopenta[b]indole-4(1H)-carboxylate (intermediate 27c) (0.4 g, 1.1 mmol) in CH2Cl2 (10 mL), cooled to 0° C., TFA (1 mL) mL) was added. The reaction mixture was warmed to room temperature and stirred for 90 min., quenched with saturated NaHCO3 (pH-8) and extracted with CH2Cl2 (3×100 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude compound. The crude material was purified by washing with 5% EtOAc-hexane (3×20 mL) to provide the title compound (250 mg, 89%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 12.16 (s, 1H), 7.48 (d, J=15.0 Hz, 1H), 7.42 (d, J=15.0 Hz, 1H), 3.19 (m, 2H), 2.92 (m, 2H).

Workup

  1. customquenched with saturated NaHCO3 (pH-8)
  2. extractionextracted with CH2Cl2 (3×100 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude compound
  6. customThe crude material was purified
  7. washby washing with 5% EtOAc-hexane (3×20 mL)

Sources & evidence

ORD record
ord-772b7350c4304ca0a9cd9dbcedcc9679
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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