(3S)-3-(Dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate → (3S)-N,N-dibenzyl-5-(5-fluoro-6-methoxypyridin-3-yl)chroman-3-amine

HRID 1099403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1099403
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].FC(F)(F)S(O[C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][C@H:22]([N:29]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:23][O:24]2)(=O)=O>>[CH2:37]([N:29]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@H:22]1[CH2:21][C:20]2[C:25](=[CH:26][CH:27]=[CH:28][C:19]=2[C:4]2[CH:5]=[N:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=2)[O:24][CH2:23]1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Komponenten

3

Edukt 2

HCID 25053925(3S)-3-(Dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonateHCID 44717400(5-Fluoro-6-methoxypyridin-3-yl)boronic acid

Produkt 1

HCID 25114692(3S)-N,N-dibenzyl-5-(5-fluoro-6-methoxypyridin-3-yl)chroman-3-amineAusbeute 71 %

Versuchsvorschrift

The title compound was synthesized as described for Intermediate example I-2 in 71% yield, starting from 5-fluoro-6-methoxypyridin-3-ylboronic acid (1.7 equiv) and (3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate (1 equiv): 1H NMR (400 MHz, DMSO-d6) δ ppm 7.96 (d, 1 H), 7.73 (dd, 1 H), 7.23-7.37 (m, 8 H), 7.06-7.22 (m, 3 H), 6.78 (dd, 2 H), 4.34 (d, 1 H), 3.92-4.08 (m, 4 H), 3.60-3.79 (m, 4 H), 3.18-3.30 (m, 1 H), 2.89-3.10 (m, 2 H); MS (ESI) m/z 455[M+H+].

Quellen und Nachweise

ORD-Eintrag
ord-4d8762ee43884da196cde1c0e12a1f64
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143408B2

Notizen zur Reaktion

Wird geladen…