Cesium fluoride → HCID 59424530, compound

HRID 500769Notes

Reaction equation

HRID 500769 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[N:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.[F-].[Cs+].C([O-])(O)=O.[Na+]>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]=[N:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)[S:10][C:9]=12

Participants

7

Reactant 4

HCID 25953Cesium fluorideHCID 516892Sodium BicarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 594245212-Bromo-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 59424530HCID 59424530, compoundYield 32.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the nitro compound 42 (500 mg, 1.36 mmol), 6-methoxypyridin-3-ylboronic acid (312 mg, 2.04 mmol) and CsF (620 mg, 4.08 mmol) were suspended in DME (12 ml) and NaHCO3 (342 mg, 4.08 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 at 80° C. for 3 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 45 (176 mg, 32% yield), which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.71 (m, 1H), 8.56 (m 1H), 8.46 (m, 1H), 8.22 (m, 2H), 8.01 (s, 1H), 7.72 (t, J=8.6 Hz, 1H), 6.99 (d, J=5.47 Hz, 1H), 6.90 (m, 1H), 3.97 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-15e2c525e5a5482ca7250b5aafaea43d
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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