Cesium fluoride → HCID 66649265, compound

HRID 418706Notes

Reaction equation

HRID 418706 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.[CH3:22][O:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:29]=1[O:30][CH3:31].C([O-])(O)=O.[Na+].[F-].[Cs+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([C:2]2[S:10][C:9]3[C:4](=[N:5][CH:6]=[CH:7][C:8]=3[O:11][C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=3[F:21])[CH:3]=2)[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]

Participants

8

Reactant 4

HCID 25953Cesium fluorideHCID 516892Sodium BicarbonateHCID 27347023,4-Dimethoxyphenylboronic acidHCID 59424521HCID 59424521, compound

Product 1

HCID 66649265HCID 66649265, compoundYield 59.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 50 (400 mg, 1.08 mmol) in DME (20 ml) was added 3,4-dimethoxyphenylboronic acid (394 mg, 2.17 mmol), NaHCO3 (273 mg, 3.25 mmol), CsF (494 mg, 3.25 mmol), Pd(PPh3)4 (125 mg, 0.11 mmol) and water (10 ml). The reaction mixture was degassed for 15 min with a nitrogen stream, and was heated to reflux for 2.5 hrs under nitrogen. After cooling to room temperature the reaction mixture was diluted with AcOEt and successively washed with water, sat. NH4Cl, brine, dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified by flash column chromatography (eluents AcOEt/CH2Cl2: 5/95 to 30/70) and triturated in AcOEt/hexanes to afford title compound 331 (273 mg, 59% yield) as a yellow solid. MS (m/z): 427.1 (M+H)+.

Workup

  1. customThe reaction mixture was degassed for 15 min with a nitrogen stream
  2. temperaturewas heated
  3. temperatureto reflux for 2.5 hrs under nitrogen
  4. additionwas diluted with AcOEt
  5. washsuccessively washed with water, sat. NH4Cl, brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash column chromatography (eluents AcOEt/CH2Cl2: 5/95 to 30/70)
  10. customtriturated in AcOEt/hexanes

Sources & evidence

ORD record
ord-1646fa518d8948c48094bbb2bf6471d0
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

Loading…