(3-Amino-4-fluorophenyl)methanol → HCID 54724208, compound

HRID 1867088Notes

Reaction equation

HRID 1867088 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[CH:6][C:7]=1[F:8].[OH:11][C:12]1[CH:17]=[C:16]([CH3:18])[O:15][C:14](=O)[CH:13]=1>ClC1C=CC=CC=1Cl>[F:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:9][OH:10])=[CH:3][C:2]=1[N:1]1[C:16]([CH3:18])=[CH:17][C:12]([OH:11])=[CH:13][C:14]1=[O:15]

Participants

4

Reactant 2

HCID 13563644(3-Amino-4-fluorophenyl)methanolHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54724208HCID 54724208, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A 100 mL round bottomed flask equipped with stirbar, Dean-Stark trap and reflux condenser was charged with (3-amino-4-fluorophenyl)methanol (4.5 g, 31.9 mmol), 4-hydroxy-6-methyl-2-pyrone (4 g, 31.9 mmol) and o-dichlorobenzene (5 mL). The system was immersed in a 170 C oil bath for 10 minutes. The solvent was removed in vacuo and the residue was chromatographed on reverse phase (75:25 water:acetonitrile with 0.05% TFA). The product contained some starting materials after purification and was used without further purification (1.27 g, 15%). 1H NMR (400 MHz, dmso-d6) δ 7.39 (m, 1H), 7.20 (dd, J=2.2 and 7.6 Hz, 1H), 6.74 (dd, J=2.7 and 9.6 Hz, 1H), 5.93 (dd, J=1.2 and 2.2 Hz, 1H), 5.22 (dd, J=0.4 and 2.2 Hz, 1H), 2.12 (s, 3H) ppm. ES-HRMS m/z 250.0862 (M+H calcd for C13H13FNO3 requires 250.0874).

Workup

  1. customA 100 mL round bottomed flask equipped with stirbar, Dean-Stark trap
  2. temperaturereflux condenser
  3. customThe solvent was removed in vacuo
  4. customthe residue was chromatographed on reverse phase (75:25 water:acetonitrile with 0.05% TFA)
  5. customafter purification
  6. customwas used without further purification (1.27 g, 15%)

Sources & evidence

ORD record
ord-239463689c914993a95e0491936274bb
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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