Cesium fluoride → Methyl 3-formyl-1-(3-(naphthalen-1-yloxy)propyl)-4-o-tolyl-1h-indole-2-carboxylate

HRID 1013303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1013303
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:29]=[O:30])=[C:5]([C:25]([O:27][CH3:28])=[O:26])[N:6]2[CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.[C:31]1([CH3:40])[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1B(O)O.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[Cs+]>O1CCCC1.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]>[CH:29]([C:4]1[C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[CH3:40])[N:6]([CH2:11][CH2:12][CH2:13][O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:5]=1[C:25]([O:27][CH3:28])=[O:26])=[O:30]

Komponenten

7

Edukt 4

HCID 25953Cesium fluorideHCID 27332672-Methylphenyl boronic acidHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 87353272Methyl 4-bromo-3-formyl-1-[3-(1-naphthalenyloxy)propyl]-1H-indole-2-carboxylate

Produkt 1

HCID 87353147Methyl 3-formyl-1-(3-(naphthalen-1-yloxy)propyl)-4-o-tolyl-1h-indole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of EXAMPLE 107B (0.5 g) and o-tolylboronic acid (175 mg) in tetrahydrofuran (5 ml) was added tris(dibenzylideneacetone)dipalladium(0) (25 mg), tri-t-butyl-phosphonium tetrafluoroborate (16 mg) and CsF (489 mg). The mixture was purged with Argon and stirred at room temperature for 24 hours. The mixture was diluted with ethyl acetate (200 mL) and washed with water and brine and dried over Na2SO4. After filtration, concentration of the solvent and column purification (5% ethyl acetate in hexane) provided EXAMPLE 107C.

Aufarbeitung

  1. customThe mixture was purged with Argon
  2. additionThe mixture was diluted with ethyl acetate (200 mL)
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration, concentration of the solvent and column purification (5% ethyl acetate in hexane)
  6. customprovided EXAMPLE 107C

Quellen und Nachweise

ORD-Eintrag
ord-5fdefe5525fa4880b1da4d8ee6d9c7b4
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981888B2

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