HCID 69938024, compound → HCID 67155020, compound

HRID 1897621Notes

Reaction equation

HRID 1897621 reaction equation
[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([O:20][CH3:21])[CH:13]=1)[CH2:3][CH:4]=[CH2:5]>[Pd].CO>[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([O:20][CH3:21])[CH:13]=1)[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 1

HCID 69938024HCID 69938024, compound

Product 1

HCID 67155020HCID 67155020, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a flask containing 4-(4-(1-hydroxy-but-3-enyl)pyridin-3-yl)-2-methoxybenzonitrile (140 mg, 0.499 mmol) and MeOH (5 mL) was added 10% Pd/C (53.1 mg, 0.050 umol), and the flask was flushed with H2. The mixture was stirred under H2 at room temperature for 10 min. The mixture was then filtered and concentrated. The residue was purified by Xbridge C18 eluting with a 20 to 70% acetonitrile-water gradient to give 4-(4-(1-hydroxybutyl)pyridin-3-yl)-2-methoxybenzonitrile. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.66 (t, J=7.3 Hz, 3H), 1.04-1.28 (m, 2H), 1.35-1.54 (m, 2H), 3.95 (s, 3H), 4.59 (ddd, J=8.2, 4.3, 4.2 Hz, 1H), 5.35 (d, J=4.0 Hz, 1H), 7.10 (dd, J=8.0, 1.4 Hz, 1H), 7.25 (d, J=1.3 Hz, 1H), 7.60 (d, J=5.3 Hz, 1H), 7.84 (d, J=7.8 Hz, 1H), 8.39 (s, 1H), 8.61 (d, J=5.1 Hz, 1H). HRMS: (ESI) ink 283.1446 [(M+H)+ Calcd for C17H18N2O2 283.1446].

Workup

  1. customthe flask was flushed with H2
  2. filtrationThe mixture was then filtered
  3. concentrationconcentrated
  4. customThe residue was purified by Xbridge
  5. washC18 eluting with a 20 to 70% acetonitrile-water gradient

Sources & evidence

ORD record
ord-85a491136d614c239c171102738fecda
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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