3-Bromo-1,1,1-trifluoro-2-propanone → HCID 86640275, compound

HRID 2092505Notes

Reaction equation

HRID 2092505 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[CH:6]=[C:7]([C:11]([F:16])([CH3:15])[C:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=1)=[S:3].Br[CH2:18][C:19](=O)[C:20]([F:23])([F:22])[F:21].[C:25]([O-])(O)=O.[Na+]>O1CCOCC1.O>[F:16][C:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([NH:4][C:2]2[S:3][CH:18]=[C:19]([C:20]([F:23])([F:22])[F:21])[N:1]=2)[CH:6]=1)([CH3:15])[C:12]([O:14][CH3:25])=[O:13]

Participants

5

Reactant 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 86640276HCID 86640276, compound

Product 1

HCID 86640275HCID 86640275, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 2-{3-[(aminocarbonothioyl)amino]phenyl}-2-fluoropropanoate (0.84 g, 3.3 mmol) in a 1:1 dioxane/water mixture (10 mL), 3-bromo-1,1,1-trifluoroacetone (0.42 mL, 4.0 mmol) was added dropwise and the mixture refluxed for 18 h. After cooling at room temperature, a saturated solution of NaHCO3 (20 mL) was added and the mixture trasferred into a separator funnel; the aqueous phase was extracted with EtOAc (3×20 mL) and the collected organic extracts dried over Na2SO4 and evaporated under vacuum to give a crude that, after purification by flash chromatography, afforded pure methyl 2-fluoro-2-(3-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanoate as yellow solid (0.89 g, yield 77%). 1H-NMR (CDCl3) δ 7.95 (bs, 1H, NH), 7.53 (s, 1H), 7.42 (m, 2H), 7.28 (s, 1H), 7.10 (s, 1H), 3.80 (s, 3H), 1.95 (d, 3H, J=23 Hz).

Workup

  1. temperaturethe mixture refluxed for 18 h
  2. customthe mixture trasferred into a separator funnel
  3. extractionthe aqueous phase was extracted with EtOAc (3×20 mL)
  4. dry with materialthe collected organic extracts dried over Na2SO4
  5. customevaporated under vacuum
  6. customto give a crude that,
  7. customafter purification by flash chromatography

Sources & evidence

ORD record
ord-9225ed68824a46d4a98cf3ae36d4f068
Source dataset
uspto-grants-2013_05
Patent number
US08440711B2

Reaction notes

Loading…