Cesium fluoride → HCID 58790194, compound

HRID 418613Notes

Reaction equation

HRID 418613 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.[N:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.[F-].[Cs+].C([O-])(O)=O.[Na+]>COCCOC.O.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>[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:25]3[CH:26]=[CH:27][N:22]=[CH:23][CH:24]=3)[S:10][C:9]=12

Participants

8

Reactant 4

HCID 25953Cesium fluorideHCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 594245212-Bromo-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 58790194HCID 58790194, compoundYield 75%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of the nitro compound 50 (890 mg, 2.41 mmol), pyridin-4-ylboronic acid (593 mg, 2 eq, 4.82 mmol), CsF (1.1 g, 3 eq, 7.23 mmol) and Pd(PPh3)4 (278 mg, 0.1 eq, 0.241 mmol) were suspended in DME (30 ml) and NaHCO3 (607 mg, 3 eq, 7.23 mmol), dissolved in the minimum amount of water, was added. The mixture was de-aerated by bubbling N2 through the solution for 10 min, heated to reflux for 4 hrs and concentrated to dryness. The formed residue was dissolved in DCM and washed with water. The DCM was collected, dried over sodium sulfate, filtered and the DCM was removed by evaporation. The resultant solid was triturated with Et2O to afford the title compound 63 (660 mg, 75% yield), which was used without further purification. MS (m/z): 368.0 (M+H).

Workup

  1. additionwas added
  2. customby bubbling N2 through the solution for 10 min
  3. temperatureheated
  4. temperatureto reflux for 4 hrs
  5. concentrationconcentrated to dryness
  6. dissolutionThe formed residue was dissolved in DCM
  7. washwashed with water
  8. customThe DCM was collected
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customthe DCM was removed by evaporation
  12. customThe resultant solid was triturated with Et2O

Sources & evidence

ORD record
ord-64ae010358104c41befd1fee28d6e2ae
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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