Trifluoroacetic acid → HCID 178515292, compound

HRID 15525Notes

Reaction equation

HRID 15525 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) at rt for 10 h. It was concentrated in vacuo and the residue was purified by flash column on silica gel eluting with hexane/EtOAc/MeOH//600:300:50 followed by hexane/EtOAc/MeOH//400:400:50:10 to obtain 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. concentrationIt was concentrated in vacuo
  2. customthe residue was purified by flash column on silica gel eluting with hexane/EtOAc/MeOH//600:300:50
  3. customto obtain an impure product which
  4. customwas triturated with a small amount of MeOH and Et2O

Sources & evidence

ORD record
ord-b898106f38ee4d7994d129c073394fd3
Source dataset
uspto-grants-2010_06
Patent number
US07732613B2

Reaction notes

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