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Cesium carbonate → HCID 66835009, compound

HRID 61921
Notes
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Reaction equation

HRID 61921 reaction equation
[CH3:1][C:2]1([CH3:28])[C:14]2[O:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10]=2C(=O)[C:8]2[C:3]1=[CH:4][C:5](OS(C(F)(F)F)(=O)=O)=[CH:6][CH:7]=2.C(=[NH:42])(C1C=CC=CC=1)C1C=CC=CC=1.[C:43](=[O:46])([O-])[O-].[Cs+].[Cs+].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>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1COCC1>[NH2:42][C:5]1[CH:4]=[C:3]2[C:8](=[CH:7][CH:6]=1)[C:43](=[O:46])[C:10]1[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[O:13][C:14]=1[C:2]2([CH3:28])[CH3:1]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 86663832Trifluoro-methanesulfonic acid 6,6-dimethyl-11-oxo-6,11-dihydro-benzo[b]naphtho[2,3-d]furan-8-yl ester

Product 1

HCID 66835009HCID 66835009, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To trifluoro-methanesulfonic acid 6,6-dimethyl-11-oxo-6,11-dihydro-benzo[b]naphtho[2,3-d]furan-8-yl ester (100 mg), benzhydrylideneamine (0.05 ml), cesium carbonate (110 mg), palladium acetate (2 mg) and BINAP (7 mg), THF (2 ml) was added. The mixture was stirred and heated at 65° C. overnight under nitrogen atmosphere, and the reaction mixture was diluted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (16 mg, 23%).

Workup

  1. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residues were purified by silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4edd0b30d30c4ae1ad02ec26b93378fb
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440922B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes