HCID 59560104, compound → HCID 59560176, compound

HRID 1643789Notes

Reaction equation

HRID 1643789 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[O:11][C:10]([C:12]([CH3:14])=[CH2:13])=[CH:9][C:8]2=[C:15]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=2)=[O:18])[CH:16]=1)([CH3:3])[CH3:2]>CO.[Pd]>[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[O:11][C:10]([CH:12]([CH3:14])[CH3:13])=[CH:9][C:8]2=[C:15]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=2)=[O:18])[CH:16]=1)([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59560104HCID 59560104, compound

Product 1

HCID 59560176HCID 59560176, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6-isopropoxy-N-(5-methylpyridin-2-yl)-2-(prop-1-en-2-yl)benzofuran-4-carboxamide (118 mg, 0.34 mmol) in 10 mL of MeOH was passed through H-cube (10 bar of H2, 15° C., 5% Pd/C cartridge) at a rate of 1.0 mL/min. The collected solution was subsequently concentrated to give a light yellow gum (65 mg, 54%). 1H NMR (400 MHz, CDCl3) δ 8.53 (s, 1 H) 8.31 (d, J=8.56 Hz, 1 H) 8.14 (s, 1 H) 7.60 (dd, J=8.44, 2.14 Hz, 1 H) 7.29 (d, J=2.01 Hz, 1 H) 7.16 (d, J=2.01 Hz, 1 H) 6.84 (s, 1 H) 4.56-4.63 (m, 1 H), 3.04-3.13 (m, 1 H), 2.34 (s, 3H), 1.37 (m, 12 H); LCMS for C21H24N2O3 m/z 353.20 (M+H)+.

Workup

  1. concentrationThe collected solution was subsequently concentrated

Sources & evidence

ORD record
ord-6aa81c8f925549638e3acba7f0c2d48c
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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