HCID 59495719, compound → HCID 59495731, compound

HRID 219839Notes

Reaction equation

HRID 219839 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]=[CH:8][C:7]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]>CO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]=[CH:8][C:7]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]

Participants

4

Reactant 1

HCID 59495719HCID 59495719, compound

Product 1

HCID 59495731HCID 59495731, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Intermediate 41 (625.12 mg; 2.23 mmol; 1 eq.) was dissolved in MeOH (50 mL). The solution was injected on a flow hydrogenation reactor (H-cube), adapted with 10% Pd/C cartridge, a flow of 0.5 mL/min, a temperature of 60° C. and the full H2 option enabled. Evaporation of the solvent afforded the title compound as a yellow oil. 1H NMR (DMSO-d6, 300 MHz) δ 7.99 (d, J=1.5 Hz, 1H), 7.92 (dd, J=7.9, 1.7 Hz, 1H), 7.23-7.14 (m, 4H), 7.02 (d, J=7.1 Hz, 1H), 3.25 (t, J=6.5 Hz, 2H), 3.20 (s, 3H), 2.56-2.47 (m, 1H), 2.41-2.31 (m, 1H), 1.97 (s, 3H), 1.65 (quintuplet, J=7.2 Hz, 2H). LC/MS (Method B): 281.2 (M−H)−. HPLC (Method A) Rt 4.25 min (Purity: 97.7%).

Workup

  1. customThe solution was injected on a flow hydrogenation reactor
  2. customa temperature of 60° C.
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f9ae0e64aeb948af9cf485879363c6cc
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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