Cesium fluoride → Acetone

HRID 1797154Notes

Reaction equation

HRID 1797154 reaction equation
[F-].[Cs+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1B(O)O.Br[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([NH:21][C:22]2[CH:26]=[C:25]([CH:27]3[CH2:29][CH2:28]3)[NH:24][N:23]=2)=[O:20])=[CH:14][CH:13]=1>COCCOC.CO>[CH:27]1([C:25]2[NH:24][N:23]=[C:22]([NH:21][C:19](=[O:20])[CH2:18][C:15]3[CH:16]=[CH:17][C:12]([C:5]4[CH:6]=[CH:7][S:3][CH:4]=4)=[CH:13][CH:14]=3)[CH:26]=2)[CH2:29][CH2:28]1.[CH3:4][C:5]([CH3:6])=[O:20]

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 27339602-Thiopheneboronic acidHCID 22176755HCID 22176755, compound

Product 2

HCID 180AcetoneYield 533.2%HCID 22176889HCID 22176889, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

330 mg (2.17 mmol) of CsF, 81 mg (0.63 mmol) of thienylboronic acid and 36 mg (0.031 mmol) of tetrakis triphenylphosphine palladium (Pd(PPh3)4 were added to 100 mg (0.31 mmol) of 2-(4-bromophenyl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)acetamide) in 25 mL of DME and 2 mL of MeOH. The mixture was shaken 48 hrs at 80° C. under nitrogen. The reaction mixture is evaporated, redissolved in ethyl acetate and then washed with a saturated solution of NaHCO3. The organic layer was, after treatment with anhydrous sodium sulfate, evaporated under reduced pressure and the title compound was obtained by crystallization from acetone (48 mg, 48% yield).

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionredissolved in ethyl acetate
  3. washwashed with a saturated solution of NaHCO3
  4. customafter treatment with anhydrous sodium sulfate, evaporated under reduced pressure

Sources & evidence

ORD record
ord-9d6e7a7df4424999b382de9b50ee9843
Source dataset
uspto-grants-2006_04
Patent number
US07034049B1

Reaction notes

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