Cesium carbonate → 2-(6-(tert-butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-chlorobenzaldehyde

HRID 407607Notes

Reaction equation

HRID 407607 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[NH:10][N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22](F)[C:19]=1[CH:20]=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].C(O[Si](C)(C)C)C>CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:22]1[CH:23]=[CH:24][CH:25]=[C:18]([Cl:17])[C:19]=1[CH:20]=[O:21])[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 15772EthoxytrimethylsilaneHCID 678472-Chloro-6-fluorobenzaldehydeHCID 594737656-(tert-Butyl)-8-fluorophthalazin-1(2H)-one

Product 1

HCID 594738282-(6-(tert-butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-chlorobenzaldehydeYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a 10 mL round bottom flask were added 6-tert-butyl-8-fluoro-2H-phthalazin-1-one 101h (640 mg, 2.9 mmol), 2-chloro-6-fluorobenzaldehyde (506 mg, 3.2 mmol), and cesium carbonate (488 mg, 1.5 mmol). The flask was evacuated and backfilled with nitrogen three times then ethoxytrimethylsilane (684 mg, 5.8 mmol) and DMF (5 mL) were added to the reaction flask. The resulting mixture was heated to 60° C. After 4 h of stirring, the solution was allowed to cool down to ambient temperature and the reaction was quenched by addition of 2 mL of H2O drop-wise. The desired product started to precipitate from the DMF and water mixture. The solid was collected by filtration after cooling down to 5° C., and washed with DMF/water (2/1, 2 mL, pre-cooled to 6° C.) and H2O (2 mL). The filter cake was dried under vacuum oven at 65° C. for overnight to afford 519 mg (52%) of 101i as a yellow solid. MS: [M+H]+: 359

Workup

  1. customThe flask was evacuated
  2. temperatureto cool down to ambient temperature
  3. customthe reaction was quenched by addition of 2 mL of H2O drop-wise
  4. customto precipitate from the DMF and water mixture
  5. filtrationThe solid was collected by filtration
  6. temperatureafter cooling down to 5° C.
  7. washwashed with DMF/water (2/1, 2 mL, pre-cooled to 6° C.) and H2O (2 mL)
  8. customThe filter cake was dried under vacuum oven at 65° C. for overnight

Sources & evidence

ORD record
ord-3593461688bb4cb6901edf0687b528aa
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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