(Pyrimidin-5-yl)boronic acid → 7-(pyrimidin-5-yl)-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

HRID 37811

Reaktionsgleichung

Reaktionsgleichung von HRID 37811
Br[C:2]1[C:10]2[NH:9][C:8]3[CH:11]4[CH2:17][CH2:16][N:14]([CH2:15][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH2:13][CH2:12]4.[N:18]1[CH:23]=[C:22](B(O)O)[CH:21]=[N:20][CH:19]=1>>[N:18]1[CH:23]=[C:22]([C:2]2[C:10]3[NH:9][C:8]4[CH:11]5[CH2:17][CH2:16][N:14]([CH2:15][C:7]=4[C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH2:13][CH2:12]5)[CH:21]=[N:20][CH:19]=1

Komponenten

3

Edukt 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 672401637-bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Produkt 1

HCID 532514307-(pyrimidin-5-yl)-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Versuchsvorschrift

The product of Example 1B (100 mg, 0.32 mmol) and pyrimidine-5-boronic acid (64 mg, 0.52 mmol; MayBridge) were processed as described in Example 4 to provide the title compound: 1H NMR (500 MHz, methanol-d4) δ ppm 2.01-2.17 (m, 4 H), 2.60 (s, 3 H), 3.03-3.14 (m, 3 H), 3.20-3.29 (m, 2 H), 4.27 (s, 2 H), 7.03-7.06 (m, 1 H), 7.10 (t, J=7.6 Hz, 1 H), 7.34 (dd, J=7.6, 1.2 Hz, 1 H), 7.42 (d, J=8.2 Hz, 1 H), 7.96 (dd, J=7.9, 2.4 Hz, 1 H), 8.63 (d, J=2.1 Hz, 1 H); MS (ESI+) m/z 291 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-e371a3fb99564f8e8868bf72c644bbd2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524703B2

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