Diisopropylamine → 2-(3-Methyl-2-pent-1-ynyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047763

Reaktionsgleichung

Reaktionsgleichung von HRID 1047763
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2I)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].C(NC(C)C)(C)C.[CH:33]#[C:34][CH2:35][CH2:36][CH3:37]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[C:33]#[C:34][CH2:35][CH2:36][CH3:37])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Komponenten

7

Edukt 3

HCID 7912DiisopropylamineHCID 123091-PentyneHCID 593141532-(2-Iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Produkt 1

HCID 593141852-(3-Methyl-2-pent-1-ynyl-benzoylamino)-indan-2-carboxylic acid ethyl esterAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (693 mg, 1.54 mmol) in anhydrous DMF (5 mL) and DIPA (diisopropylamine, 10 mL) is added Pd(PPh3)4 (89 mg, 7.7% mmol), CuI (29 mg, 0.154 mmol) and pent-1-yne (1.5 mL, 15.4 mmol). The resulting solution is covered in argon and run in a microwave reaction: 110° C., 35 minutes. After the removal of DMF and DIPA in vacuo, the residue is dissolved in EtOAc (100 mL) and washed with water (1×10 mL) and brine (2×10 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (120 g silica gel, gradient elution: 0%-40% EtOAc in heptane) to give a pure product (122) as a pale yellow solid (144 mg, 24%).

Aufarbeitung

  1. customrun in a microwave reaction
  2. custom110° C., 35 minutes
  3. customAfter the removal of DMF and DIPA in vacuo
  4. dissolutionthe residue is dissolved in EtOAc (100 mL)
  5. washwashed with water (1×10 mL) and brine (2×10 mL)
  6. dry with materialThe organic layer is dried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash column chromatography (120 g silica gel, gradient elution: 0%-40% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-4ef08da1335d42d18ed9f84076b1da93
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569535B2

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