HCID 67227793, compound → HCID 53251555, compound

HRID 1515739Notes

Reaction equation

HRID 1515739 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:19]2[NH:27][C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)=[CH:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>[Pd].CO>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([C:19]2[NH:27][C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)[CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 67227793HCID 67227793, compound

Product 1

HCID 53251555HCID 53251555, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-pyran-2(S)-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (220 mg, 5.7 mmol) and 10% palladium on activated carbon (66 mg) in methanol (200 mL) was heated at 50° C. under hydrogen (50 psi) and kept for 16 h. The mixture was cooled to 25° C., the catalyst was removed by filtration and then washed with ethyl acetate and the filtrate 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 0.1% ammonium hydroxide in water) afforded 2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-pyran-2-yl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (60 mg, 27%) as a mixture of two diastereoisomers: LC/MS m/e calcd for C21H24N2O3S [M+H]+ 385.50, observed 385.2; 1H NMR (400 MHz, CDCl3) δ ppm 1.34-1.67 (m, 5H), 1.82 (m, 1H), 2.15 (m, 1H), 2.36 (m, 1H), 3.05, 3.09 (2×s, 3H), 3.21-3.40 (m, 2H), 4.13, 4.18 (2×m, 1H), 4.61, 4.67 (2×dd, 1H), 6.33, 6.42 (2×s, 1H), 7.18, 7.26 (2×m, 1H), 7.52, 7.59 (d, J=8.5 Hz, 2H), 7.89, 7.94 (2×m, 3H), 8.16 (m, 1H), 11.47 (br, 1H).

Workup

  1. temperatureThe mixture was cooled to 25° C.
  2. customthe catalyst was removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationthe filtrate concentrated in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-58dd2bbfbba2453eb6675bb4704300c8
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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