Ammonium fluoride → HCID 57405227, compound

HRID 632852Notes

Reaction equation

HRID 632852 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][Si](C(C)(C)C)(C)C)[C:6]([CH2:23][N:24]1[C:28]3[CH:29]=[N:30][CH:31]=[CH:32][C:27]=3[N:26]([CH:33]3[CH2:35][CH2:34]3)[C:25]1=[O:36])=[CH:5]2.[F-].[NH4+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[C:6]([CH2:23][N:24]1[C:28]3[CH:29]=[N:30][CH:31]=[CH:32][C:27]=3[N:26]([CH:33]3[CH2:35][CH2:34]3)[C:25]1=[O:36])=[CH:5]2

Participants

4

Reactant 2

HCID 25516Ammonium fluorideHCID 67975286HCID 67975286, compound

Product 1

HCID 57405227HCID 57405227, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The intermediate 11 (1.06 g, 1.14 mmol) was dissolved in methanol (30 mL), and then ammonium fluoride (0.172 g, 4.6 mmol) was added. The resulting mixture was stirred at 60° C. overnight. The reaction mixture was allowed to cool down to room temperature, then the solvent was removed. The residue was purified by column chromatography dichloromethane methanol to yield the product as a white solid (323 mg, 62%). m/z=456 (M+H)+.

Workup

  1. temperatureto cool down to room temperature
  2. customthe solvent was removed
  3. customThe residue was purified by column chromatography dichloromethane methanol

Sources & evidence

ORD record
ord-18cbcad3721144fa8f9df3b75aa09d14
Source dataset
uspto-grants-2016_04
Patent number
US09321768B2

Reaction notes

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