Phosphorus oxychloride → 6-Bromo-2-(4-(trifluoromethyl)phenyl)oxazolo[5,4-b]pyridine

HRID 710112Notes

Reaction equation

HRID 710112 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[C:5](O)=[N:6][CH:7]=1.O=P(Cl)(Cl)Cl.CCOC(C)=O.O>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=3)[O:21][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 22728543Water ethylacetateHCID 178418902HCID 178418902, compound

Product 1

HCID 711142156-Bromo-2-(4-(trifluoromethyl)phenyl)oxazolo[5,4-b]pyridineYield 64.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Intermediate 56 (2.1 g, 5.4 mmol) was dissolved in Dioxane (30 ml) and added POCl3 (1.5 ml). This mixture was refluxed for 5 h. After 5 h, dioxane was removed on rotavapour to obtain the residue. Work up (EtOAc/H2O) of the residue afforded the crude. Crude was purified by column on 60-120 mesh silica gel using DCM as eluent to afford the titled compound (1.2 g). 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.46 (d, J 2.1, 1H), 8.41 (d, J 8.2, 2H), 8.24 (d, J 2.1, 1H), 7.83 (d, J 8.2, 2H).

Workup

  1. temperatureThis mixture was refluxed for 5 h
  2. customdioxane was removed on rotavapour
  3. customto obtain the residue
  4. customafforded the crude
  5. customCrude was purified by column on 60-120 mesh silica gel

Sources & evidence

ORD record
ord-7d8c012fd0544ca29720b0a9a622e741
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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