HCID 67229073, compound → 3-[2-(4-methanesulfonyl-phenyl)-2-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-cyclopentanone

HRID 1515791Notes

Reaction equation

HRID 1515791 reaction equation
O1[C:5]2([CH2:9][CH2:8][CH:7](/[CH:10]=[C:11](\[C:22]3[NH:30][C:25]4=[N:26][CH:27]=[CH:28][CH:29]=[C:24]4[CH:23]=3)/[C:12]3[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=3)[CH2:6]2)[O:4]CC1>[Pd].CO>[CH3:21][S:18]([C:15]1[CH:14]=[CH:13][C:12]([CH:11]([C:22]2[NH:30][C:25]3=[N:26][CH:27]=[CH:28][CH:29]=[C:24]3[CH:23]=2)[CH2:10][CH:7]2[CH2:8][CH2:9][C:5](=[O:4])[CH2:6]2)=[CH:17][CH:16]=1)(=[O:19])=[O:20]

Participants

4

Reactant 1

HCID 67229073HCID 67229073, compound

Product 1

HCID 532518703-[2-(4-methanesulfonyl-phenyl)-2-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-cyclopentanoneYield 6.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (Z)-2-[2-(1,4-dioxa-spiro[4.4]non-7-yl)-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (enantiomer 1, prepared as in Example 78, 140 mg, 0.33 mmol) and 10% palladium on activated carbon (50 mg) in methanol (125 mL) was heated at 50° C. under hydrogen (50 psi) for 96 h. The mixture was cooled to 25° C., the catalyst was filtered off, washed with ethyl acetate and concentrated in vacuo. Purification 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 0.05% trifluoroacetic acid in water) afforded 3-[2-(4-methanesulfonyl-phenyl)-2-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-cyclopentanone (diastereomer 1, 8 mg, 6%): LC/MS m/e calcd for C21H22N2O3S [M+H]+ 383.49, observed 383.0; 1H NMR (400 MHz, CD3OD) δ ppm 8.09 (d, J=4.5 Hz, 1H), 7.90 (d, J=7.8 Hz, 2H), 7.63 (d, J=7.8 Hz, 2H), 7.05 (dd, J=7.7, 4.9 Hz, 1H), 6.43 (d, J=3.0 Hz, 1H), 4.75-4.84 (m, 1H), 4.59 (br. s., 1H), 4.38 (t, J=7.8 Hz, 1H), 3.08 (s, 2H), 2.37-2.49 (m, 1H), 2.05-2.30 (m, 4H), 1.88-1.99 (m, 1H), 1.58-1.71 (m, 1H), 1.22-1.38 (m, 1H), 0.90 (t, J=6.6 Hz, 1H).

Workup

  1. temperatureThe mixture was cooled to 25° C.
  2. filtrationthe catalyst was filtered off
  3. washwashed with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-07ba0655c01d41d7a728d6e0350b349d
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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