HCID 86638321, compound → HCID 24857885, compound

HRID 523126Notes

Reaction equation

HRID 523126 reaction equation
C([O:3][P:4]([C:9]([C:12]1[C:21]([Br:22])=[CH:20][C:19]2[C:14](=[CH:15][C:16]([C:23]#[N:24])=[CH:17][CH:18]=2)[CH:13]=1)([F:11])[F:10])(=[O:8])[O:5]CC)C>ClCCl.C[Si](Br)(C)C>[Br:22][C:21]1[C:12]([C:9]([P:4](=[O:3])([OH:8])[OH:5])([F:10])[F:11])=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([C:23]#[N:24])[CH:15]=2

Participants

4

Reactant 1

HCID 86638321HCID 86638321, compound

Product 1

HCID 24857885HCID 24857885, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 76113BromotrimethylsilaneSolvent

Procedure

A solution of diethyl[(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonate (2.2 g) in dichloromethane (5 mL) and TMSBr (7 mL) was stirred overnight and concentrated. The residue was co-evaporated with dichloromethane (2×), ethanol/water (2×) and then dissolved in 20 mL of methanol. Ammonia (30%) was then added with vigorous stirring and the mixture was concentrated and co-evaporated with methanol (3×). The solid residue was washed with ether to give the desired product as a white powder. MS(−ESI): m/z 360.0 and 361.9 (M−1)−.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in 20 mL of methanol
  3. additionAmmonia (30%) was then added
  4. concentrationthe mixture was concentrated and co-evaporated with methanol (3×)
  5. washThe solid residue was washed with ether

Sources & evidence

ORD record
ord-5348bd0ca7b0475fb3f16098a8d761bb
Source dataset
uspto-grants-2016_05
Patent number
US09334295B2

Reaction notes

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