2-Iodotoluene → HCID 68940392, compound

HRID 2199756Notes

Reaction equation

HRID 2199756 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:17]=2[NH:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14]3)O1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[Cs+].I[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[CH3:51]>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].CO.O1CCOCC1>[C:46]1([CH3:51])[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14]2

Participants

8

Reactant 4

HCID 51282-IodotolueneHCID 25953Cesium fluorideHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 16050160Ethyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylate

Product 1

HCID 68940392HCID 68940392, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of ethyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylate (Paul et al. J. Am. Chem. Soc. 2006, 128, 15552-15553) (1.6 g), tri-(t-butyl)phosphonium tetrafluoroborate (0.074 g), tris(dibenzylideneacetone)dipalladium(0) (0.116 g) and cesium fluoride (2.313 g) was added ortho-iodotoluene (0.781 ml), then dioxane (200 ml) and methanol (20 ml). The reaction mixture was immediately purged with nitrogen and stirred at room temperature for 2 hours. Additional amounts of (dibenzylideneacetone)dipalladium(0) (0.116 g), ortho-iodotoluene (0.781 ml), CsF (2.313 g), and tri-(t-butyl)phosphonium tetrafluoroborate (0.074 g) were added at the same time. The resulting solution was stirred at room temperature overnight. The insoluble material was filtered off and the filtrate was concentrated and the residue was purified by flash chromatography, eluting with 0-100% dichloromethane in hexane to provide the title compound.

Workup

  1. customThe reaction mixture was immediately purged with nitrogen
  2. additionAdditional amounts of (dibenzylideneacetone)dipalladium(0) (0.116 g), ortho-iodotoluene (0.781 ml), CsF (2.313 g), and tri-(t-butyl)phosphonium tetrafluoroborate (0.074 g) were added at the same time
  3. stirringThe resulting solution was stirred at room temperature overnight
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated
  6. customthe residue was purified by flash chromatography
  7. washeluting with 0-100% dichloromethane in hexane

Sources & evidence

ORD record
ord-a733100975754e9c8b12cfb804ff773c
Source dataset
uspto-grants-2016_06
Patent number
US09359296B2

Reaction notes

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