(4,4-Difluoropiperidin-1-yl)[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]methanone → [6-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

HRID 19888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19888
[F:1][C:2]1([F:29])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:22][CH2:21]2)=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1.Cl.[Br:31]C1C=C2C(C=C(C(O)=O)N2)=CC=1OC1CCN(C(C)C)CC1.BrC1C=C2C(C=C(C(N3CCOCC3)=O)N2C2C=CN=C(Cl)C=2)=CC=1OC1CCN(C(C)C)CC1>>[Br:31][C:14]1[CH:13]=[C:12]2[C:17]([CH:18]=[C:10]([C:8]([N:5]3[CH2:6][CH2:7][C:2]([F:1])([F:29])[CH2:3][CH2:4]3)=[O:9])[NH:11]2)=[CH:16][C:15]=1[O:19][CH:20]1[CH2:25][CH2:24][N:23]([CH:26]([CH3:27])[CH3:28])[CH2:22][CH2:21]1

Komponenten

4

Edukt 3

HCID 11603838(4,4-Difluoropiperidin-1-yl)[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]methanoneHCID 16739659[6-Bromo-1-(2-chloro-pyridin-4-yl)-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-morpholin-4-yl-methanoneHCID 670179306-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid hydrochloride

Produkt 1

HCID 67017928[6-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

Versuchsvorschrift

In analogy to the procedure described for the synthesis of intermediate 1, step 4, the title compound was synthesized from 6-bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid hydrochloride salt with 1 eq. lithium chloride (example 41, step 5). The title compound was obtained in 77% yield as light yellow solid. MS (m/e): 486.2 (MH+, 100%).

Quellen und Nachweise

ORD-Eintrag
ord-e9c38c43e6db468594ffe30ce7151a38
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745479B2

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