Cesium carbonate → HCID 86725381, compound

HRID 1503826Notes

Reaction equation

HRID 1503826 reaction equation
[CH2:1]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]1[C:14]([F:15])=[CH:13][C:12](Br)=[CH:11][C:10]=1[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:25]1([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH2:1]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]1[C:14]([F:15])=[CH:13][C:12]([N:28]2[CH2:27][CH2:26][N:25]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29]2)=[CH:11][C:10]=1[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 11143579HCID 11143579, compound

Product 1

HCID 86725381HCID 86725381, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product of Example 16B (490 mg, 1.3 mmol), tert-butyl piperazine-1-carboxylate (258 mg, 1.4 mmol), palladium diacetate (14 mg, 0.06 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (59 mg, 0.09 mmol) and cesium carbonate (848 mg, 2.6 mmol) in 1,4-dioxane (10 mL) was heated at reflux for 16 hours. The mixture was filtered through diatomaceous earth and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 8/1 petroleum ether/ethyl acetate to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. filtrationThe mixture was filtered through diatomaceous earth
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  6. washeluting with 8/1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-0f51df264be449e7acedb4c6d5569a04
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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