Methanol → 5-(6,7-Dimethoxyquinolin-4-yloxy)pyridin-2-amine

HRID 1433490Notes

Reaction equation

HRID 1433490 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][CH:11]=1.CO.O1CCCC1.C(N(CC)CC)C>[C].[Pd].C(OCC)(=O)C>[CH3:21][O:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[O:22][CH3:23])[N:13]=[CH:12][CH:11]=[C:10]2[O:9][C:3]1[CH:4]=[CH:5][C:6]([NH2:8])=[N:7][CH:2]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 229368366-Chloro-5-(6,7-dimethoxyquinolin-4-yloxy)pyridin-2-ylamine

Product 1

HCID 229365375-(6,7-Dimethoxyquinolin-4-yloxy)pyridin-2-amineYield 31%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

After suspending 6-chloro-5-(6,7-dimethoxyquinolin-4-yloxy)pyridin-2-ylamine (500 mg, 1.51 mmol) in a mixed solvent of methanol (20 ml), tetrahydrofuran (10 ml) and triethylamine (3 ml), palladium carbon (300 mg) was added and the mixture was stirred for 15 hours at room temperature under a hydrogen atmosphere. The catalyst was filtered off by celite filtration, washing was performed with ethanol, and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate), and the fraction containing the target substance was concentrated, suspended in ethyl acetate and diluted with hexane, after which the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (138 mg, 0.465 mmol, 31%) as colorless crystals.

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered off by celite filtration
  3. washwashing
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. additionthe fraction containing the target substance
  7. concentrationwas concentrated
  8. additiondiluted with hexane
  9. filtrationafter which the crystals were filtered out
  10. washwashed with hexane
  11. customblow-dried

Sources & evidence

ORD record
ord-78c7d5bf6ba14414a594048fa4b9271d
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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