Benzyltriphenylphosphonium bromide → 8-Phenethylbenzo[f][1,7]naphthyridin-5-amine

HRID 340321

Reaktionsgleichung

Reaktionsgleichung von HRID 340321
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[CH:12]=[CH:13][C:14]([CH:16]=O)=[CH:15][C:4]=2[N:3]=1.[Br-].[CH2:19]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:16]([C:14]1[CH:13]=[CH:12][C:5]2=[C:6]3[C:11](=[C:2]([NH2:1])[N:3]=[C:4]2[CH:15]=1)[N:10]=[CH:9][CH:8]=[CH:7]3)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

3

Edukt 2

HCID 2734970Benzyltriphenylphosphonium bromideHCID 866523555-Aminobenzo[f][1,7]naphthyridine-8-carbaldehyde

Produkt 1

HCID 582137798-Phenethylbenzo[f][1,7]naphthyridin-5-amine

Versuchsvorschrift

8-Phenethylbenzo[f][1,7]naphthyridin-5-amine was prepared from 5-aminobenzo[f][1,7]naphthyridine-8-carbaldehyde (from Example 87) with benzyltriphenylphosphonium bromide following the procedures described for Example 91 (wittig reaction) and Example 92 (reduction). 1H NMR (acetone-d6): δ 8.99 (dd, 1H), 8.88 (dd, 1H), 8.35 (d, 1H), 7.83 (dd, 1H), 7.49 (d, 1H), 7.29-7.15 (dd, 6H), 6.70 (br s, 2H), 3.10-3.00 (m, 4H). LRMS [M+H]=300.1.

Aufarbeitung

  1. customdescribed for Example 91 (wittig reaction) and Example 92 (reduction)

Quellen und Nachweise

ORD-Eintrag
ord-34cec331caf449b1985d8e1a8a81128d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895577B2

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