HCID 67228834, compound → HCID 53251714, compound

HRID 1515763Notes

Reaction equation

HRID 1515763 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH:7]=[C:8]([C:19]2[NH:27][C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[CH2:3][CH2:2]1>[Pd].CO>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH:8]([C:19]2[NH:27][C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)[C:9]2[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 67228834HCID 67228834, compound

Product 1

HCID 53251714HCID 53251714, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[2-(tetrahydro-pyran-4-yl)-1-(4-trifluoromethyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (170 mg, 4.5 mmol) and 10% palladium on activated carbon (51 mg) in methanol (200 mL) was heated at 50° C. under hydrogen (50 psi) and kept for 6 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-[2-(tetrahydro-pyran-4-yl)-1-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (60 mg, 35%) as a white solid: LC/MS m/e calcd for C21H21F3N2O [M+H]+ 375.41, observed 375.4; 1H NMR (400 MHz, CDCl3) δ ppm 8.12 (d, J=4.5 Hz, 1H), 7.92 (d, J=7.6 Hz, 1H), 7.49-7.58 (m, J=8.1 Hz, 2H), 7.39-7.47 (m, J=8.1 Hz, 2H), 7.09 (dd, J=7.6, 5.1 Hz, 1H), 6.36 (s, 1H), 4.39 (t, J=7.8 Hz, 1H), 3.92 (d, J=11.1 Hz, 2H), 3.27 (t, J=11.6 Hz, 2H), 2.26 (dt, J=14.1, 7.2 Hz, 1H), 2.03 (dt, J=14.0, 7.0 Hz, 1H), 1.66 (d, J=12.4 Hz, 2H), 1.33-1.56 (m, 3H).

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-698a7bf301974a719d6da6b11763bebc
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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