3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → US8865911, 46b Isomer 2

HRID 539360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539360
Br[C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1([CH2:12][CH2:11][CH2:10][O:9][CH2:8]1)[CH2:6][C:5]12[N:20]=[C:19]([NH2:21])[C:18]([CH3:22])=[N:17]1.[Cl:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:29]=1[F:30]>>[Cl:23][C:24]1[CH:25]=[C:26]([C:2]2[CH:3]=[C:4]3[C:14](=[CH:15][CH:16]=2)[O:13][C:7]2([CH2:12][CH2:11][CH2:10][O:9][CH2:8]2)[CH2:6][C:5]23[N:20]=[C:19]([NH2:21])[C:18]([CH3:22])=[N:17]2)[CH:27]=[CH:28][C:29]=1[F:30]

Komponenten

3

Edukt 2

HCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 573861526'-Bromo-5-methyl-5'',6''-dihydro-4''H-dispiro[imidazole-2,4'-chromene-2',3''-pyran]-4-amine

Produkt 1

HCID 57386154US8865911, 46b Isomer 2Ausbeute 27,6 %

Versuchsvorschrift

6′-Bromo-5-methyl-5″,6″-dihydro-4″H-dispiro[imidazole-2,4′-chromene-2′,3″-pyran]-4-amine (Example 45 Isomer 2, 77 mg, 0.21 mmol), and 3-chloro-4-fluorophenylboronic acid (47.9 mg, 0.27 mmol) was reacted using the conditions described for Example 46a Isomer 1, to give Isomer 2 of the title compound, (24 mg, 27% yield) with undetermined configuration: 1H NMR (500 MHz, DMSO-d6) δ ppm 1.41-1.54 (m, 1 H), 1.78-1.92 (m, 3 H), 1.99-2.13 (m, 2 H), 2.25 (s, 3 H), 3.40-3.47 (m, 1 H), 3.54 (d, 1 H), 3.68-3.74 (m, 1 H), 3.94 (d, 1 H), 6.53 (br. s, 2 H), 6.58 (d, 1 H), 6.94 (d, 1 H), 7.39-7.46 (m, 3 H), 7.58-7.63 (m, 1 H); MS (ES+) m/z 414 [M+H]+.

Quellen und Nachweise

ORD-Eintrag
ord-faa25b40655b4a10a8e0b392677bca35
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865911B2

Notizen zur Reaktion

Wird geladen…