Hydrochloric Acid → HCID 67363585, compound

HRID 1183184Notes

Reaction equation

HRID 1183184 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[N:6]=1)=[O:4].[F:19][B-](F)(F)F.F[B-](F)(F)F.Cl[N+]12CC[N+](F)(CC1)CC2C.C(OCC)C.Cl>C(#N)C.O>[CH3:1][O:2][C:3]([C:5]1[C:9]([F:19])=[C:8]([O:10][CH3:11])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[N:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67363124HCID 67363124, compoundHCID 178429830HCID 178429830, compound

Product 1

HCID 67363585HCID 67363585, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

200 mg (0.8 mmol) of 1-(2-fluoro-phenyl)-5-methoxy-1H-pyrazole-3-carboxylic acid methyl ester were dissolved in 2 ml of acetonitrile and 745 mg (1.99 mmol) of 1-chloro-methyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor®) were added. The mixture was stirred overnight. Then, irrespective of the incomplete reaction, diethyl ether, water and 2 N hydrochloric acid were added, the organic phase was separated, the solvent evaporated and the residue subjected to preparative HPLC. 70 mg (33%) of the title compound were obtained.

Workup

  1. additionwere added
  2. customthe organic phase was separated
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-e4c1a94de74d4cc49eda661390f6c929
Source dataset
uspto-grants-2014_03
Patent number
US08664257B2

Reaction notes

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