2-[(E)-2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine → 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 1515889Notes

Reaction equation

HRID 1515889 reaction equation
[CH:1]1(/[CH:6]=[C:7](/[C:18]2[NH:27][C:21]3=[N:22][CH:23]=[C:24]([F:26])[CH:25]=[C:20]3[CH:19]=2)\[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:27][C:21]3=[N:22][CH:23]=[C:24]([F:26])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 532502852-[(E)-2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 583052382-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridineYield 41%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine (prepared as in Example 116, 147 mg, 0.38 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-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine as a white solid (60 mg, 41%): LC/MS m/e calcd for C21H23FN2O2S [M+H]+ 387.49, observed 387.2; 1H NMR (400 MHz, CD3OD) δ ppm 8.00 (t, J=2.3 Hz, 1H), 7.90 (d, J=8.3 Hz, 2H), 7.58-7.66 (m, 3H), 6.40 (s, 1H), 4.31 (t, J=8.0 Hz, 1H), 3.09 (s, 3H), 2.24-2.32 (m, 1H), 2.08-2.16 (m, 1H), 1.60-1.87 (m, 5H), 1.45-1.56 (m, 2H), 1.18-1.30 (m, 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-8db7e6604aa84f6a9999e22974dcea10
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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