Ammonium Chloride → HCID 86692074, compound

HRID 509263Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)=[O:9])[CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[C:19]([F:22])([F:21])[F:20].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>C1COCC1.CO>[Br:1][C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][C:13]([OH:16])([C:19]([F:22])([F:21])[F:20])[CH2:12][CH2:11]2)=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

After 1-(6-bromopicolinoyl)piperidin-4-one (100 mg, 0.353 mmol) was dissolved in THF (1.5 ml), trimethyl(trifluoromethyl)silane (0.5M solution in THF, 1.4 ml, 0.706 mmol) and tetrabutylammonium fluoride (1.0M solution in THF, 0.74 ml, 0.741 mmol) were sequentially added thereto at 0° C., and then the resulting mixture was stirred at room temperature for 13 hours. A saturated aqueous ammonium chloride solution (0.6 ml) was added to the resulting reaction liquid, and then the resulting mixture was stirred for 10 minutes, followed by extraction with MC (10 ml×2). The organic layer was dried over anhydrous magnesium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (3% MeOH/MC), to obtain 120 mg of white solid (97%).

Workup

stirringthe resulting mixture was stirred for 10 minutes
extractionfollowed by extraction with MC (10 ml×2)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfollowed by filtration and concentration
customthe residue thus obtained

Sources & evidence

ORD record: ord-f3b1abcc8f214ec3bd4b2b333e74dd2f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096571B2

Reaction notes

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