Triethylamine → HCID 66592896, compound

HRID 1091836Notes

Reaction equation

HRID 1091836 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]2[C:11]3[C:12](Cl)=[N:13][CH:14]=[CH:15][C:16]=3[O:17][C:9]=2[C:8]([O:19][CH3:20])=[CH:7][CH:6]=1)=[O:4].C(N(CC)CC)C.[H][H]>[Pd].CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:10]2[C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:16]=3[O:17][C:9]=2[C:8]([O:19][CH3:20])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 86636829HCID 86636829, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66592896HCID 66592896, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of Methyl-1-chloro-6-Methoxybenzo[4,5]furo[3,2-c]pyridine-9-carboxylate (from step 11) (330 mg), 10% Pd on carbon (50 mg), triethyl amine (2.0 mL) and DMF (10.0 mL) was hydrogenated in a Parr apparatus at 50-55 psi of Hydrogen gas. Catalyst was removed by filtration and filtrate was concentrated under vacuo. The residue obtained was purified by silica gel column using chloroform:acetone (8:2) as an eluent to afford intermediate-13 (200 mg) as light yellow solid.

Workup

  1. customCatalyst was removed by filtration and filtrate
  2. concentrationwas concentrated under vacuo
  3. customThe residue obtained
  4. customwas purified by silica gel column
  5. customto afford intermediate-13 (200 mg) as light yellow solid

Sources & evidence

ORD record
ord-78731c4f7a94479da9f68e74fabe09ce
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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