Tetramethylammonium fluoride → HCID 59843071, compound

HRID 1878787Notes

Reaction equation

HRID 1878787 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13](=[O:16])[N:12]([CH2:17][CH2:18][O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[CH:22][CH:21]=3)[N:11]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[F:32][C:33]([Si](C)(C)C)([F:35])[F:34].[F-].C[N+](C)(C)C>COCCOC>[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13](=[O:16])[N:12]([CH2:17][CH2:18][O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[CH:22][CH:21]=3)[N:11]=2)[CH:7]=[CH:6][C:3]=1[CH:4]([OH:5])[C:33]([F:35])([F:34])[F:32]

Participants

5

Reactant 3

HCID 67803Tetramethylammonium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 86624661HCID 86624661, compound

Product 1

HCID 59843071HCID 59843071, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 2-chloro-4-(1-(2-(7-methoxyquinolin-4-yloxy)ethyl)-6-oxo-1,6-dihydropyridazin-3-yl)benzaldehyde (370 mg, 849 μmol) and (trifluoromethyl)trimethylsilane (121 μL, 849 μmol) in DME (10 mL) at −50° C. under nitrogen was added solid tetramethylammonium fluoride (79 mg, 849 μmol). The reaction was then removed from cooling bath and slowly warmed to 0°C. The reaction was then partitioned between DCM (100 mL) and 5% NaHCO3 (50 mL). The organic was dried over MgSO4, concentrated under reduced pressure, then purified on silica (40 g) eluting with 2 to 3% of MeOH/DCM. Product was isolated as an off white solid. MS (ESI pos. ion) m/z: 506 (MH+); calc'd for C24H19ClF3N3O4: 505.

Workup

  1. customThe reaction was then removed
  2. temperaturefrom cooling bath
  3. customThe reaction was then partitioned between DCM (100 mL) and 5% NaHCO3 (50 mL)
  4. dry with materialThe organic was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified on silica (40 g)
  7. washeluting with 2 to 3% of MeOH/DCM
  8. customProduct was isolated as an off white solid

Sources & evidence

ORD record
ord-0c105494f6d7444694f7fbcb3d6c0329
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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