Potassium Fluoride → HCID 89907307, compound

HRID 923988Notes

Reaction equation

HRID 923988 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH:23]12[NH:31][CH:27]([CH2:28][O:29][CH2:30]1)[CH2:26][O:25][CH2:24]2.[F-].[K+]>CN(C=O)C.CCOC(C)=O>[CH:27]12[N:31]([C:3]3[C:2]([Br:1])=[CH:21][C:6]([C:7]([NH:9][C:10]4[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=4)=[O:8])=[CH:5][N:4]=3)[CH:23]([CH2:30][O:29][CH2:28]1)[CH2:24][O:25][CH2:26]2

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 115284333,7-dioxa-9-azabicyclo[3.3.1]nonaneHCID 867025955-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 89907307HCID 89907307, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

5-Bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 12.2, 55.4 mg, 0.14 mmol) and 3,7-Dioxa-9-aza-bicyclo[3.3.1]nonane (Organic Chemistry (2006), 71(1), 413-415) (24.53 mg, 0.14 mmol) were dissolved in DMF (150 μL). KF (24.4 mg, 0.42 mmol) was added and the RM mixture was stirred at 140° C. for 18 h in a pressure safe vial. After cooling at RT, the RM was dissolved in EtOAc and washed with brine. The organic phase was dried over Na2SO4 and evaporated to dryness under reduced pressure to give a residue that was purified by flash chromatography (RediSep® Silica gel column, n-hexane/EtOAc from 20% to 60% EtOAc) to afford the title compound as a white solid. HPLC (Condition 4) tR=5.84 min, UPLC-MS (Condition 3) tR=1.19 min, m/z=490.1 [M+H]+.

Workup

  1. temperatureAfter cooling at RT
  2. washwashed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated to dryness under reduced pressure
  5. customto give a residue that
  6. customwas purified by flash chromatography (RediSep® Silica gel column, n-hexane/EtOAc from 20% to 60% EtOAc)

Sources & evidence

ORD record
ord-a9cf88691fb446908bde43ee5469818f
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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