Trifluoroacetic acid → HCID 178515292, compound

HRID 2374022Notes

Reaction equation

HRID 2374022 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9](O)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]=1[OH:8].C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC>C(Cl)Cl>[CH2:9]([C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[C:7]=1[OH:8])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 1785152933-Bromo-5-(hydroxy(phenyl)methyl)pyridin-4-ol

Product 1

HCID 178515292HCID 178515292, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-bromo-5-(hydroxy(phenyl)methyl)pyridin-4-ol (2.55 g, 91 mmol), TFA (16 mL) and Et3SiH in CH2Cl2 (30 mL) was stirred at rt for 10 h. The reaction mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel eluting with hexane/EtOAc/MeOH//600:300:50 followed by hexane/EtOAc/MeOH 11400:400:50:10 to afford an impure product which was triturated with a small amount of MeOH and Et2O to obtain the desired product (255 mg, 10%) as a white solid. 1H NMR (DMSO-d6) δ 11.75 (br s, 1H), 8.13 (s, 1H), 7.54 (s, 1H), 7.26-7.14 (m, 5H), 2.49 (s, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash column chromatography on silica gel eluting with hexane/EtOAc/MeOH//600:300:50
  3. customto afford an impure product which
  4. customwas triturated with a small amount of MeOH and Et2O

Sources & evidence

ORD record
ord-3f3df3e575754836a5d887c8b76bf5b4
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

Loading…