Phosphate → 5-Bromo-2-(2,5-dimethyl-pyrrol-1-yl)-4-trifluoromethyl-thiazole

HRID 1660758Notes

Reaction equation

HRID 1660758 reaction equation
[CH3:1][C:2](=O)[CH2:3][CH2:4][C:5](=O)[CH3:6].Br.[Br:10][C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[C:17]([F:20])([F:19])[F:18].P([O-])([O-])([O-])=O>CO>[Br:10][C:11]1[S:15][C:14]([N:16]2[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]2[CH3:6])=[N:13][C:12]=1[C:17]([F:20])([F:19])[F:18]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 80352,5-HexanedioneHCID 848198665-Bromo-4-(trifluoromethyl)thiazol-2-amine hydrobromide

Product 1

HCID 674291065-Bromo-2-(2,5-dimethyl-pyrrol-1-yl)-4-trifluoromethyl-thiazoleYield 1,261%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add hexane-2,5-dione (3.5 mL, 3.4 g, 30 2 mmol) to a solution of 5-bromo-4-trifluoromethyl-thiazol-2-ylamine hydrobromide (9.0 g, 27.4 mmol) in methanol (60 mL). Stir at room temperature overnight. Add phosphate buffer (50 mL, pH=7). Collect the resulting precipitate by filtration, washing with water. Dissolve the filter cake in CH2Cl2 and dry over sodium sulfate. Filter and concentrate under vacuum to obtain the title compound (8.2 g, 92%). 1H NMR (400 MHz, CDCl3) δ 5.91 (s, 2H), 2.27 (s, 6H).

Workup

  1. customCollect the resulting precipitate
  2. filtrationby filtration
  3. washwashing with water
  4. dissolutionDissolve the filter cake in CH2Cl2
  5. dry with materialdry over sodium sulfate
  6. filtrationFilter
  7. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-a7672010c46c48a5a9179be5e5718cb1
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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