Potassium Carbonate → HCID 68002595, compound

HRID 1051851Notes

Reaction equation

HRID 1051851 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].Cl.[F:20][CH:21]1[CH2:24][NH:23][CH2:22]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:23]2[CH2:24][CH:21]([F:20])[CH2:22]2)=[O:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 101250543-fluoroazetidine HydrochlorideHCID 162158674-Bromo-3-methoxybenzoic acid

Product 1

HCID 68002595HCID 68002595, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-bromo-3-methoxybenzoic acid (1.4 g) in DMF (15 mL) was added potassium carbonate (2.51 g), 3-fluoroazetidine hydrochloride (1.01 g) and HATU (3.69 g). The mixture was stirred at room temperature for 18 h. Water was added, the mixture was stirred for 15 minutes and the solvent was removed in vacuum. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with water, saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum, to give 1.25 g of the title compound.

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. customthe solvent was removed in vacuum
  3. additionWater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with water, saturated sodium chloride solution
  6. dry with materialdried (sodium sulfate)
  7. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-80228d604a9344f9bfec3691205c24b0
Source dataset
uspto-grants-2016_07
Patent number
US09388177B2

Reaction notes

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