2-Fluoropyridine → HCID 58047091, compound

HRID 1888783Notes

Reaction equation

HRID 1888783 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:24]=[CH:23][C:13]3[CH:14]=[C:15]([CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])[O:16][C:12]=3[CH:11]=2)=[CH:4][CH:3]=1.F[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[N:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[CH:24]=[CH:23][C:13]3[CH:14]=[C:15]([CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])[O:16][C:12]=3[CH:11]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 97462-FluoropyridineHCID 11430Potassium CarbonateHCID 58047041HCID 58047041, compound

Product 1

HCID 58047091HCID 58047091, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-(1-{6-[2-(4-hydroxyphenyl)ethyl]-1-benzofuran-2-yl}ethyl)acetamide (40.0 mg, 0.123 mmol) obtained in Example 165, 2-fluoropyridine (0.0369 mL, 0.371 mmol) and potassium carbonate (51.3 mg, 0.371 mmol) were stirred in DMSO (0.5 mL) at 100° C. for 2 days. The reaction mixture was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:0 to 2:3), and the solvent was evaporated. The residue was triturated with a small amount of diisopropyl ether to give the title compound (17.1 mg, yield 35%) as a white solid.

Workup

  1. customThe reaction mixture was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:0 to 2:3)
  2. customthe solvent was evaporated
  3. customThe residue was triturated with a small amount of diisopropyl ether

Sources & evidence

ORD record
ord-15266a8b2b974411a08250e3f3315f7c
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

Loading…