HCID 67228928, compound → HCID 53252025, compound

HRID 1515802Notes

Reaction equation

HRID 1515802 reaction equation
[CH:1]1([CH:6]=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:28])([CH:25]([CH3:27])[CH3:26])[CH3:24])=[CH:19][CH:18]=2)[C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][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:17]2[CH:18]=[CH:19][C:20]([C:23]([OH:28])([CH:25]([CH3:26])[CH3:27])[CH3:24])=[CH:21][CH:22]=2)[C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 67228928HCID 67228928, compound

Product 1

HCID 53252025HCID 53252025, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-phenyl}-3-methyl-butan-2-ol (50 mg, 0.13 mmol) and 10% palladium on activated carbon (15 mg) in methanol (250 mL) was heated at 50° C. under hydrogen (50 psi) for 16 h. The mixture was cooled to 25° C., the solids 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-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-phenyl}-3-methyl-butan-2-ol (30 mg, 60%): LC/MS m/e calcd for C25H32N2O [M+H]+ 377.55, observed 377.2; 1H NMR (400 MHz, CD3OD) δ ppm 0.80 (d, J=6.82 Hz, 4H) 0.86 (d, J=6.82 Hz, 4H) 1.20-1.31 (m, 1H) 1.46-1.53 (m, 5H) 1.59-1.77 (m, 3H) 1.97 (t, J=6.82 Hz, 1H) 2.05-2.13 (m, 1H) 2.19-2.26 (m, 1H) 4.17 (t, J=7.96 Hz, 1H) 6.33 (s, 1H) 7.04 (dd, J=7.71, 4.93 Hz, 1H) 7.28 (m, J=8.34 Hz, 2H) 7.38 (m, J=8.08 Hz, 2H) 7.89 (dd, J=7.83, 1.26 Hz, 1H) 8.06 (d, J=3.79 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-55fe5586bec54f5f912954b66a565db9
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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