Toluene → HCID 56655538, compound

HRID 1038996Notes

Reaction equation

HRID 1038996 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[F:12].[F:13][C:14]([F:34])([F:33])[O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:26][CH2:25][C:24]3([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[C:23]2=[O:32])=[CH:18][CH:17]=1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[F:12][C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[N:29]1[CH2:30][CH2:31][C:24]2([C:23](=[O:32])[N:22]([C:19]3[CH:18]=[CH:17][C:16]([O:15][C:14]([F:33])([F:13])[F:34])=[CH:21][CH:20]=3)[CH2:26][CH2:25]2)[CH2:27][CH2:28]1

Participants

8

Reactant 4

HCID 1140TolueneHCID 1424144-Bromo-3-fluorobenzotrifluorideHCID 23676156Sodium t-butoxideHCID 667427592-(4-(Trifluoromethoxy)phenyl)-2,8-diazaspiro[4.5]decan-1-one

Product 1

HCID 56655538HCID 56655538, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A sealed tube was charged with 4-bromo-3-fluorobenzotrifluoride (40 mg, 0.16 mmol), 2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (50 mg, 0.16 mmol), sodium tert-butoxide (17 mg, 0.18 mmol), tris(dibenzylidene acetone)dipalladium-(0) (15 mg, 0.02 mmol), BINAP (5 mg, 0.01 mmol) and toluene (2) under argon. The sealed tube was closed and immersed in an oil bath and heated to 80° C. for 15 h. The reaction mixture was allowed to cool to room temperature, diluted in ethyl acetate, filtered, and concentrated in vacuo to give a crude residue which was purified by flash column chromatography to yield the title compound as a light yellow solid (50 mg, 66%). MS (ESI): 477.1 (MH+)

Workup

  1. customThe sealed tube was closed
  2. customimmersed in an oil bath
  3. temperatureto cool to room temperature
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a crude residue which
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-74d344748a2c48e6882aff6226167989
Source dataset
uspto-grants-2013_10
Patent number
US08552024B2

Reaction notes

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