Water → HCID 68706474, compound

HRID 222114Notes

Reaction equation

HRID 222114 reaction equation
[NH:1]1[C:5]2[C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[CH2:12][CH2:13][C:4]=2[C:3]([C:14]([O:16][CH3:17])=[O:15])=[CH:2]1.O([CH2:26][C:27]([F:30])([F:29])[F:28])S(C(F)(F)F)(=O)=O.O>CN(C=O)C>[F:28][C:27]([F:30])([F:29])[CH2:26][N:1]1[C:5]2[C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[CH2:12][CH2:13][C:4]=2[C:3]([C:14]([O:16][CH3:17])=[O:15])=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 68705905HCID 68705905, compound

Product 1

HCID 68706474HCID 68706474, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of methyl 4,5-dihydro-1H-pyrrolo[2,3-f]isoquinoline-3-carboxylate E1 (0.44 mmol) in dry DMF (5 mL) NaH (0.52 mmol) was added. The reaction mixture was stirred at rt for 2 h. After cooling to 0° C., trifluoroethyl triflate (0.52 mmol) in DMF (5 mL) was added dropwise. The mixture was maintained at rt overnight and then poured into icy water and extracted with DCM. The organic layer was dried (Na2SO4) and concentrated. Purification by chromatography on silica gel (eluant: DCM/acetone 9:1) afforded the title compound (65% yield). ESI (+) MS: m/z 311 (MH+). 1H NMR: 2.82 (t, J=7.70, 2H), 2.92 (t, J=7.70, 2H), 3.76 (s, 3H), 5.41 (q, J=8.90, 2H), 7.56 (d, J=5.24, 1H), 7.75 (s, 1H), 8.41 (d, J=5.24, 1H), 8.44 (s, 1H).

Workup

  1. temperatureAfter cooling to 0° C.
  2. temperatureThe mixture was maintained at rt overnight
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by chromatography on silica gel (eluant: DCM/acetone 9:1)

Sources & evidence

ORD record
ord-0d2d896d1d514faebac5e2c851d8f114
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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