Diisopropylethylamine → 5-Bromo-2-(2-cyclobutoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047751
[CH:1]1([O:5][C:6]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:10])=O)[CH2:4][CH2:3][CH2:2]1.[CH2:16]([O:18][C:19]([C:21]1([NH2:31])[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Br:30])[CH:27]=2)[CH2:22]1)=[O:20])[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:16]([O:18][C:19]([C:21]1([NH:31][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[C:14]([CH3:15])[C:6]=2[O:5][CH:1]2[CH2:2][CH2:3][CH2:4]2)[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Br:30])[CH:27]=2)[CH2:22]1)=[O:20])[CH3:17]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 593141552-Cyclobutyloxy-3-methylbenzoic acidHCID 59314228Ethyl 2-amino-5-bromo-2,3-dihydro-1H-indene-2-carboxylate

Produkt 1

HCID 593143855-Bromo-2-(2-cyclobutoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl esterAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-cyclobutoxy-3-methyl-benzoic acid (250 mg, 1.21 mmol), 2-amino-5-bromo-indan-2-carboxylic acid ethyl ester (344 mg, 1.21 mmol), HATU (551 mg, 1.45 mmol) in anhydrous DMF (10 mL) is added DIPEA (240 μL, 1.45 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (50 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: 5%-70% EtOAc in heptane) to give a pure product (100) as a colorless oil (520 mg, 91%).

Aufarbeitung

  1. customAfter the removal of DMF in vacuo
  2. dissolutionthe residue is dissolved in EtOAc (50 mL)
  3. washwashed with water (1×10 mL) and brine (2×10 mL)
  4. dry with materialThe organic layer is dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash column chromatography (120 g silica gel, gradient elution: 5%-70% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-0749e6b1fbe7486c8967dafbc6dac9cc
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569535B2

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