HCID 68706474, compound → HCID 24989584, compound

HRID 222115Notes

Reaction equation

HRID 222115 reaction equation
[F:1][C:2]([F:22])([F:21])[CH2:3][N:4]1[C:8]2[C:9]3[CH:10]=[CH:11][N:12]=[CH:13][C:14]=3[CH2:15][CH2:16][C:7]=2[C:6]([C:17]([O:19]C)=[O:18])=[CH:5]1.O.O.[Li]>C1COCC1.O.CO>[F:22][C:2]([F:1])([F:21])[CH2:3][N:4]1[C:8]2[C:9]3[CH:10]=[CH:11][N:12]=[CH:13][C:14]=3[CH2:15][CH2:16][C:7]=2[C:6]([C:17]([OH:19])=[O:18])=[CH:5]1

Participants

4

Reactant 2

HCID 68706474HCID 68706474, compoundHCID 86640251HCID 86640251, compound

Product 1

HCID 24989584HCID 24989584, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of methyl 1-(2,2,2-trifluoroethyl)-4,5-dihydro-1H -pyrrolo[2,3-f]isoquinoline-3-carboxylate E3 (0.13 mmol) in THF/water/MeOH 8:1:1 lithium hydrate monohydrate (0.39 mmol) was added. The reaction mixture was refluxed for 8 h then the solvent was removed under reduced pressure. The residue was dissolved in water, the solution was neutralized with diluted aq potassium hydrogenosulphate and extracted with DCM/water 9:1. The organic layer was dried (Na2SO4) and evaporated to dryness. Trituration with diethylether provided the title compound. The aqueous layer was concentrated and the residue was cromatographed on silica gel (eluant: DCM/MeOH/30% NH3 90:9:1). The title compound was isolated in 60% overall yield. ESI (+) MS: m/z 297 (MH+). MS (ES−) 295. 1H NMR: 5.43 (q, J=8.98, 2H), 7.70 (d, J=5.73, 1H), 7.76 (s, 1H), 8.48 (d, J=5.61, 1H), 8.51 (s, 1H), 12.32 (s, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with DCM/water 9:1
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-af000cd729bc4a15b8a27fa65db27d9a
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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