Cesium fluoride → HCID 59457734, compound

HRID 418607Notes

Reaction equation

HRID 418607 reaction equation
Br[C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[F:21])[CH:3]=1.[OH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C([O-])(O)=O.[Na+].[F-].[Cs+]>COCCOC.O>[F:21][C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[O:11][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:3]=[C:2]([C:27]3[CH:28]=[CH:29][C:24]([CH2:23][OH:22])=[CH:25][CH:26]=3)[S:10][C:9]=12

Participants

7

Reactant 4

HCID 25953Cesium fluorideHCID 516892Sodium BicarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 594245212-Bromo-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 59457734HCID 59457734, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 50 (1.0 g, 2.71 mmol) in dry DME (20 ml) was added 4-(hydroxymethyl)phenylboronic acid (823 mg, 5.4 mmol), NaHCO3 (682 mg, 8.13 mmol), CsF (820 mg, 5.4 mmol) and water (10 ml), and the reaction mixture was refluxed under nitrogen for 2 hrs. After cooling to room temperature the solvent was removed under reduced pressure, the residue was dissolved in EtOAc and the resultant solution was washed with water, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated and the resultant solid was triturated with Et2O to afford the title compound 51 as a white solid (880 mg, 82% yield). MS (m/z): 397.1 (M+H).

Workup

  1. temperaturethe reaction mixture was refluxed under nitrogen for 2 hrs
  2. customwas removed under reduced pressure
  3. dissolutionthe residue was dissolved in EtOAc
  4. washthe resultant solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customthe resultant solid was triturated with Et2O

Sources & evidence

ORD record
ord-061f8c8473564630a0dc26547a1df772
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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