Triethylamine → HCID 66592896, compound

HRID 548974Notes

Reaction equation

HRID 548974 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-cb47ec7a0a174415b62e3469fe4946ba
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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