Diisopropylethylamine → 5-Fluoro-2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047787
[I:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:12]([O:14][C:15]([C:17]1([NH2:27])[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([F:26])[CH:23]=2)[CH2:18]1)=[O:16])[CH3:13].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>[CH2:12]([O:14][C:15]([C:17]1([NH:27][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=2[I:1])[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([F:26])[CH:23]=2)[CH2:18]1)=[O:16])[CH3:13]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 27593652-Iodo-3-methylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59314154Ethyl 2-amino-5-fluoro-2,3-dihydro-1H-indene-2-carboxylate

Produkt 1

HCID 593142075-Fluoro-2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl esterAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-iodo-3-methyl-benzoic acid (3.85 g, 14.7 mmol), 2-amino-5-fluoro-indan-2-carboxylic acid ethyl ester (3.00 g, 13.4 mmol), HATU (6.10 g, 16.1 mmol) in anhydrous DMF (6 mL) is added DIPEA (3.30 mL, 20.1 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is recrystallized from EtOAc to give a pure product (147) as white solid (3.90 g, 62%).

Aufarbeitung

  1. customAfter the removal of DMF in vacuo
  2. customthe residue is recrystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-2d70f59a7eab4c2f8a927f62b0e2ea3e
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569535B2

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