Ethanol → HCID 59810811, compound

HRID 2113725Notes

Reaction equation

HRID 2113725 reaction equation
C(O[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]([C:20]3[N:25]=[C:24]4[N:26]([CH:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)[N:27]=[C:28]([CH2:29][CH3:30])[C:23]4=[CH:22][CH:21]=3)=[CH:18][CH:17]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([OH:39])C>[Pd]>[CH2:29]([C:28]1[C:23]2[C:24](=[N:25][C:20]([C:19]3[N:15]([C:12]4[CH:13]=[C:14]([OH:39])[CH:9]=[CH:10][CH:11]=4)[N:16]=[CH:17][CH:18]=3)=[CH:21][CH:22]=2)[N:26]([CH:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[N:27]=1)[CH3:30]

Participants

4

Reactant 2

HCID 702EthanolHCID 59810843HCID 59810843, compound

Product 1

HCID 59810811HCID 59810811, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

6-{1-[4-(benzyloxy)phenyl]-1H-pyrazol-5-yl}-3-ethyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine (290 mg, 0.60 mmol) and ethanol (30 mL) were added to a Parr bottle. 10% Pd/C (150 mg, 0.14 mmol) was added, and the mixture was shaken under an atmosphere of hydrogen (45 psi) for 4 hours. The reaction was degassed under reduced pressure, flushed with argon for 5 minutes, filtered through Celite and concentrated to yield 0.23 g 3-{5-[3-ethyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-1H-pyrazol-1-yl}phenol as an oil. LC/MS (EI) tR 2.87 (Method E), m/z 390.2 (M++1). 1H NMR (CDCl3) δ 1.4 (t, 3H); 1.7 (m, 2H); 2.2 (m, 2H); 3.0 (q, 2H); 3.5 (t, 2H); 4.0 (m, 2H); 4.5 (m, 1H); 6.7-6.9 (m, 3H); 7.0 (s, 1H); 7.2 (m, 1H); 7.3 (d, 2H); 7.7 (s, 1H); 8.0 (m, 1H).

Workup

  1. customThe reaction was degassed under reduced pressure
  2. customflushed with argon for 5 minutes
  3. filtrationfiltered through Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fc88d289f3ec40f2856ea085ea0729c7
Source dataset
uspto-grants-2008_10
Patent number
US07432266B2

Reaction notes

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