HCID 67228167, compound → HCID 53250919, compound

HRID 1515670Notes

Reaction equation

HRID 1515670 reaction equation
[CH:1]1([CH:6]=[C:7]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([OH:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=2)[C:8]2[NH:18][C:11]3=[N:12][CH:13]=[C:14]([O:16][CH3:17])[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:19]2[CH:24]=[CH:23][C:22]([C:25]([OH:28])([CH3:26])[CH3:27])=[CH:21][CH:20]=2)[C:8]2[NH:18][C:11]3=[N:12][CH:13]=[C:14]([O:16][CH3:17])[CH:15]=[C:10]3[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 67228167HCID 67228167, compound

Product 1

HCID 53250919HCID 53250919, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-{4-[2-cyclopentyl-1-(5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-phenyl}-propan-2-ol (100 mg, 0.266 mmol) and 10% palladium on activated carbon (50 mg) in methanol (200 mL) was heated at 50° C. under hydrogen (50 psi) for 6 h. The mixture was cooled to room temperature. The catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo and 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-{4-[2-cyclopentyl-1-(5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-phenyl}-propan-2-ol (24 mg, 24%) as a white solid: LC/MS m/e calcd for C24H30N2O2 [M+H]+ 379.52, observed 379.2; 1H NMR (400 MHz, CD3OD) δ ppm 1.21 (m, 2H), 1.48 (m, 2H), 1.50 (s, 6H), 1.57-1.91 (m, 5H, H), 2.08 (m, 1H), 2.17 (m, 1H), 3.86 (s, 3H), 4.12 (t, J=7.8 Hz, 1H), 6.30 (s, 1H), 7.27 (d, J=8.3 Hz, 2H), 7.42 (d, J=8.3 Hz, 2H), 7.58 (d, J=2.5 Hz, 1H), 7.82 (br, 1H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe catalyst was removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified

Sources & evidence

ORD record
ord-51ef9f889de4448c99f73fdb291d71d6
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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