Ammonia → Diammonium[(6-bromo-2-cyanoquinolin-7-yl)(difluoro)methyl]phosphonate

HRID 523133Notes

Reaction equation

HRID 523133 reaction equation
C([O:3][P:4]([C:9]([C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([C:22]#[N:23])=[N:19]2)=[CH:14][C:13]=1[Br:24])([F:11])[F:10])(=[O:8])[O:5]CC)C.Br[Si](C)(C)C.[NH3:30].CO>ClCCl>[Br:24][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:12]=1[C:9]([P:4](=[O:3])([O-:5])[O-:8])([F:11])[F:10])[N:19]=[C:18]([C:22]#[N:23])[CH:17]=[CH:16]2.[NH4+:30].[NH4+:19]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 76113BromotrimethylsilaneHCID 86638326Diethyl[(6-bromo-2-cyanoquinolin-7-yl)(difluoro)methyl]phosphonate

Product 1

HCID 67501574Diammonium[(6-bromo-2-cyanoquinolin-7-yl)(difluoro)methyl]phosphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of diethyl[(6-bromo-2-cyanoquinolin-7-yl)(difluoro)methyl]phosphonate (370 mg, 0.883 mmol) in dichloromethane (9) at 0° C. was added dropwise bromotrimethylsilane (1.15 mL, 8.83 mmol). The reaction mixture was stirred at room temperature overnight. It was concentrated to dryness, and co-evaporated with dichloromethane (2×). Ethanol (5 mL) was added to the residue, which was stirred for 20 minutes. It was concentrated to dryness and co-evaporated with ethanol (2×). The residue was dissolved in methanol (8 mL) and 2.0 M ammonia in methanol (4.4 mL, 8.80 mmol) was added dropwise. It was stirred for 20 minutes, concentrated to dryness and suspended in diethyl ether. The precipitate was filtered to afford diammonium[(6-bromo-2-cyanoquinolin-7-yl)(difluoro)methyl]phosphonate.

Workup

  1. concentrationIt was concentrated to dryness
  2. additionEthanol (5 mL) was added to the residue, which
  3. stirringwas stirred for 20 minutes
  4. concentrationIt was concentrated to dryness and co-evaporated with ethanol (2×)
  5. dissolutionThe residue was dissolved in methanol (8 mL)
  6. stirringIt was stirred for 20 minutes
  7. concentrationconcentrated to dryness
  8. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-9d819738468e46bb823119b1c93ca415
Source dataset
uspto-grants-2016_05
Patent number
US09334295B2

Reaction notes

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