Sodium Bicarbonate → HCID 86679808, compound

HRID 1754563Notes

Reaction equation

HRID 1754563 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[C:9]([F:16])=[CH:10][C:11]([I:15])=[C:12]([CH:14]=1)[NH2:13].[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[N:23]1[CH:27]=[C:26]([C:28](F)=[O:29])[CH:25]=[N:24]1.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:7][C:8]1[C:9]([F:16])=[CH:10][C:11]([I:15])=[C:12]([NH:13][C:28]([C:26]2[CH:25]=[N:24][N:23]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:17]3)[CH:27]=2)=[O:29])[CH:14]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 247872515-Chloro-4-fluoro-2-iodobenzenamineHCID 86039217HCID 86039217, compound

Product 1

HCID 86679808HCID 86679808, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium t-butoxide (12.52 g, 111.6 mmol) is added at room temperature to a solution of 5-chloro-4-fluoro-2-iodoaniline (5.0 g, 22.3 mmol) in 250 mL of anhydrous THF under nitrogen. After stirring for 15 minutes, a solution of 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxylic acid fluoride (5.67 g, 24.6 mmol) in 30 mL of anhydrous THF is added dropwise. The reaction mixture is stirred for 4 hours at room temperature and then poured into saturated aqueous NaHCO3 solution and extracted with EtOAc. The organic phase is washed with saturated aqueous NaCl solution, dried over Na2SO4 and concentrated to dryness. After purification by flash chromatography on silica (cyclohexene/EtOAc: 95/5 to 80/20), a red solid is obtained, which is purified by flash chromatography on amine phase (DCM) to give 2.84 g of a white solid (yield: 31%).

Workup

  1. stirringThe reaction mixture is stirred for 4 hours at room temperature
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with saturated aqueous NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customAfter purification by flash chromatography on silica (cyclohexene/EtOAc: 95/5 to 80/20)
  7. customa red solid is obtained
  8. customwhich is purified by flash chromatography on amine phase (DCM)

Sources & evidence

ORD record
ord-82f952c4b9d14ea888cf2bc662e58f7a
Source dataset
uspto-grants-2015_10
Patent number
US09169246B2

Reaction notes

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