Aniline → HCID 68689719, compound

HRID 1296236Notes

Reaction equation

HRID 1296236 reaction equation
C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[C:22]([O:26][C:27]([N:29]1[CH2:47][CH2:46][N:32]2[C:33](=[O:45])[C:34]3[C:39]([C@@H:31]2[CH2:30]1)=[CH:38][C:37](Br)=[CH:36][C:35]=3[C:41]([F:44])([F:43])[F:42])=[O:28])([CH3:25])([CH3:24])[CH3:23].[NH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:22]([O:26][C:27]([N:29]1[CH2:47][CH2:46][N:32]2[C:33](=[O:45])[C:34]3[C:39]([C@@H:31]2[CH2:30]1)=[CH:38][C:37]([NH:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[CH:36][C:35]=3[C:41]([F:44])([F:43])[F:42])=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 6115AnilineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 16115648HCID 16115648, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 68689719HCID 68689719, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 1140TolueneSolvent

Procedure

To a degassed solution of tris(dibenzylideneacetone) dipalladium(0) (7 mg, 0.007 mmol) and 2-(di-tert-butylphosphino)biphenyl (6 mg, 0.021 mmol) in toluene (2 mL) was added N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-bromo-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one (50 mg, 0.115 mmol). The mixture was degassed (alternating vacuum and argon) and aniline (0.031 mL, 0.345 mmol) and sodium tert-butoxide (33 mg, 0.345 mmol) were added. The mixture was degassed a final time and then subjected to microwave conditions (150° C., 1800 sec). The mixture was diluted with saturated aqueous sodium chloride and ethyl acetate, and the layers were separated. The aqueous layer was washed with ethyl acetate (×2) and the combined organic layers were dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by radial chromatography (10–20% ethyl acetate in hexanes) to give 28 mg (55%) of a pale yellow residue. MS (ESI) 448 (M+H).

Workup

  1. additionwere added
  2. customThe mixture was degassed a final time
  3. customsubjected to microwave conditions (150° C., 1800 sec)
  4. additionThe mixture was diluted with saturated aqueous sodium chloride and ethyl acetate
  5. customthe layers were separated
  6. washThe aqueous layer was washed with ethyl acetate (×2)
  7. dry with materialthe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting residue was purified by radial chromatography (10–20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d3dd993b6ffa49feaa3f5d5f360ffdd5
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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