Cesium carbonate → HCID 86602345, compound

HRID 751519Notes

Reaction equation

HRID 751519 reaction equation
FC(S(O[C:9]1[C:17]2[CH:16]=[CH:15][O:14][C:13]=2[C:12]([C:18]2[C:19](=[O:35])[N:20]([CH3:34])[C:21](=[O:33])[C:22]=2[C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH3:32])[CH:24]=2)=[CH:11][CH:10]=1)(=O)=O)(F)F.[C:36](=[NH:49])([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=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+]>C1(C)C=CC=CC=1.C(OCC)C>[C:36](=[N:49][C:9]1[C:17]2[CH:16]=[CH:15][O:14][C:13]=2[C:12]([C:18]2[C:19](=[O:35])[N:20]([CH3:34])[C:21](=[O:33])[C:22]=2[C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH3:32])[CH:24]=2)=[CH:11][CH:10]=1)([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 86602346HCID 86602346, compound

Product 1

HCID 86602345HCID 86602345, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Heat a mixture of 7-[1-methyl-4-(1-methylindol-3-yl)-2,5-dioxo-3-pyrrolin-3-yl]benzo[b]fur-4-yl (trifluoromethyl)sulfonate (100 mg, 0.2 mmol), benzophenone imine (0.037 ml, 0.22 mmol), tris-(benzylideneacetone)-dipalladium(0)(9 mg, 0.01 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (19 mg, 0.03 mmol), and cesium carbonate (91 mg, 0.28 mmol) in anhydrous toluene (1 ml) to 80° C. for 19 hours under a nitrogen atmosphere. Allow the reaction to cool to room temperature, dilute with diethyl ether, and filter through Celite. Wash the filtrate with water, brine, dry over magnesium sulfate, filter and concentrate. Flash chromatography over silica gel (ethyl acetate: hexanes) affords the title compound as a red oil. MS(ES+): 536.1.

Workup

  1. temperatureHeat
  2. customthe reaction
  3. filtrationfilter through Celite
  4. washWash the filtrate with water, brine
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-f0ff9949ce3040db912a7be6043fa86e
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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