Water → HCID 67253413, compound

HRID 2042041Notes

Reaction equation

HRID 2042041 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].CC(C)([O-])C.[K+].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([O:23][CH3:24])[CH:18]=1.O>CC(N(C)C)=O>[F:9][C:3]1[CH:4]=[C:5]([O:8][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 962WaterHCID 27359194-Amino-3-fluorophenolHCID 226385104-Chloro-2-methoxypyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 67253413HCID 67253413, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 4-amino-3-fluorophenol (0.20 g, 1.6 mmol) in 4 mL of anhydrous DMA was treated with potassium tert-butoxide (0.24 g, 1.9 mmol). The resultant dark-red solution was stirred at RT for 1 hour in a capped vial. 4-Chloro-2-methoxypyridine (0.26 g, 1.6 mmol) was added and the reaction mixture was heated overnight at 100° C. Water (50 mL) was added and the solution was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by silica gel column chromatography to obtain 2-fluoro-4-(2-methoxypyridin-4-yloxy)benzenamine (0.20 g, 58% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.02 (d, J=6.0 Hz, 1H), 6.95 (dd, J=2.8, 12.0 Hz, 1H), 6.82 (dd, J=8.4, 8.8 Hz, 1H), 6.73 (dd, J=2.0, 8.4 Hz, 1H), 6.54 (dd, J=2.4, 6.0 Hz, 1H), 6.10 (d, J=2.4 Hz, 1H), 5.17 (s, 1H), 3.81 (s, 3H); MS (ESI) m/z: 235.0 (M+H+).

Workup

  1. temperaturethe reaction mixture was heated overnight at 100° C
  2. extractionthe solution was extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-7dd4077dd2f1495681558b9c62c51d99
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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