2-Fluoropyridine → HCID 59373935, compound

HRID 473699Notes

Reaction equation

HRID 473699 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[CH3:10][N:11]1[C:15](=O)[CH2:14][CH2:13][CH2:12]1.FC1C=CC=CN=1>CCOC(C)=O>[F:9][C:4]1[CH:3]=[C:2]([NH:1][C:12]2[CH:13]=[CH:14][CH:15]=[CH:10][N:11]=2)[CH:7]=[CH:6][C:5]=1[OH:8]

Participants

5

Reactant 3

HCID 97462-FluoropyridineHCID 13387N-methyl-2-pyrrolidoneHCID 2735918Phenol, 4-amino-2-fluoro-

Product 1

HCID 59373935HCID 59373935, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To 4-amino-2-fluorophenol (0.983 g, 7.73 mmol) was added NMP (3 mL) and 2-fluoropyridine (0.670 mL, 7.78 mmol). The reaction mixture was heated to 120° C. for 12.5 h and the temperature was increased to 150° C. After 9 h, the reaction mixture was diluted with EtOAc and the organic phase was washed with saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (10% to 70% EtOAc in hexanes) gave 2-fluoro-4-(pyridin-2-ylamino)phenol as a pale yellow oil. MS (ESI, pos. ion) m/z: 205.2 (M+1).

Workup

  1. temperaturethe temperature was increased to 150° C
  2. washthe organic phase was washed with saturated NaHCO3 (1×), brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography on silica gel (10% to 70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-16e84d64c15a46a786cd396e4a90acd0
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

Loading…