HCID 67229073, compound → HCID 67229389, compound

HRID 1515789Notes

Reaction equation

HRID 1515789 reaction equation
[O:1]1[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][CH2:3][CH2:2]1>[Pd].CO>[O:4]1[C:5]2([CH2:9][CH2:8][CH:7]([CH2:10][CH: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:1][CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 67229073HCID 67229073, compound

Product 1

HCID 67229389HCID 67229389, compoundYield 56.9%

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 2, 150 mg, 0.35 mmol) and 10% palladium on activated carbon (45 mg) in methanol (250 mL) was heated at 50° C. under hydrogen (50 psi) for 5 h. The mixture was cooled to 25° C., the catalyst 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 0.1% ammonium hydroxide in water) afforded 2-[2-(1,4-dioxa-spiro[4.4]non-7-yl)-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (85 mg, 56%): LC/MS m/e calcd for C23H26N2O4S [M+H]+ 427.54, observed 427.1.

Workup

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

Sources & evidence

ORD record
ord-bfd0fa7d066746ae9d9ea008c838bde1
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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