Ammonium fluoride → HCID 57405227, compound

HRID 1410543Notes

Reaction equation

HRID 1410543 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-c98f2454b0a74e5ea219f60ef472b8f8
Source dataset
uspto-grants-2014_12
Patent number
US08921560B2

Reaction notes

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