3-[(4-Fluorophenyl)methoxy]pyridin-2-amine → HCID 178490396, compound

HRID 1654825Notes

Reaction equation

HRID 1654825 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[ClH:17].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](=[NH:31])OCC)=[CH:22][CH:21]=1>C(O)C>[ClH:17].[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:8][C:7]2[C:2]([NH:1][C:27](=[NH:31])[CH2:26][C:23]3[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 27283773-[(4-Fluorophenyl)methoxy]pyridin-2-amineHCID 12238406Ethyl 4-methoxyphenylacetimidate hydrochloride

Product 1

HCID 178490396HCID 178490396, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-3-(4-fluorobenzyloxy)pyridine (4.36 g, 20 mmol) and ethyl 4-methoxyphenylacetimidate hydrochloride (5.04 g, 22 mmol) in ethanol (80 ml) was heated under reflux for 2 hours. Evaporation of the solvent gave an oil, which was purified by flash chromatography (chloroform/methanol) to obtain the product as a hygroscopic gum (1.2 g), m.p. 199°-200° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customEvaporation of the solvent
  4. customgave an oil, which
  5. customwas purified by flash chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-8a96943a563b45878b5f87d5265b321e
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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