2-Iodotoluene → HCID 68940392, 화합물

HRID 2199756노트

반응식

HRID 2199756 반응식
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

참가 물질

8

반응물 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

생성물 1

HCID 68940392HCID 68940392, 화합물

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 887Methanol용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a733100975754e9c8b12cfb804ff773c
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359296B2

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