HCID 67228295, compound → 2-{4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-phenyl}-propan-2-ol

HRID 1515892Notes

Reaction equation

HRID 1515892 reaction equation
[CH:1]1([CH:6]=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=2)[C:8]2[NH:17][C:11]3=[N:12][CH:13]=[C:14]([F:16])[CH:15]=[C:10]3[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([CH2:6][CH:7]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:27])([CH3:25])[CH3:26])=[CH:20][CH:19]=2)[C:8]2[NH:17][C:11]3=[N:12][CH:13]=[C:14]([F:16])[CH:15]=[C:10]3[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 67228295HCID 67228295, compound

Product 1

HCID 583052262-{4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-phenyl}-propan-2-olYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-{4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-phenyl}-propan-2-ol (150 mg, 0.41 mmol) and 10% palladium on activated carbon (0.2 g) in methanol (50 mL) was heated at 50° C. under hydrogen (50 psi) for 5 h. After cooling to room temperature, the catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo. The residue was purified using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) to afford 2-{4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-phenyl}-propan-2-ol (60 mg, 40%) as a white solid: LC/MS m/e calcd for C23H27FN2O [M+H]+ 367.48, observed 367.3; 1H NMR (400 MHz, MeOD) 1H NMR (400 MHz, MeOD) δ ppm 7.96 (t, J=2.5 Hz, 1H), 7.61 (dd, J=9.2, 2.5 Hz, 1H), 7.43 (d, J=8.3 Hz, 2H), 7.28 (d, J=8.3 Hz, 2H), 6.31 (s, 1H), 4.14 (t, J=7.7 Hz, 1H), 2.05-2.25 (m, 2H), 1.57-1.89 (m, 5H), 1.51 (s, 6H), 1.43-1.50 (m, 2H), 1.21 (d, J=8.6 Hz, 2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe catalyst was removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified

Sources & evidence

ORD record
ord-6bf38e092d514330ad14bc677ab147a4
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

Loading…