Isopropyltriphenylphosphonium bromide → 8-Isobutylbenzo[f][1,7]naphthyridin-5-amine

HRID 1479606Notes

Reaction equation

HRID 1479606 reaction equation
[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-].[CH:19]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:21])[CH3:20]>>[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)[CH:19]([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 2795292Isopropyltriphenylphosphonium bromideHCID 866523555-Aminobenzo[f][1,7]naphthyridine-8-carbaldehyde

Product 1

HCID 582136758-Isobutylbenzo[f][1,7]naphthyridin-5-amine

Procedure

8-Isobutylbenzo[f][1,7]naphthyridin-5-amine was prepared from 5-aminobenzo[f][1,7]naphthyridine-8-carbaldehyde (from Example 87) with isopropyl(triphenyl)phosphonium bromide following the procedures described for Example 91 (wittig reaction) and Example 92 (reduction). 1H NMR (acetone-d6): δ 8.98 (dd, 1H), 8.88 (dd, 1H), 8.35 (d, 1H), 7.82 (dd, 1H), 7.44 (d, 1H), 7.18 (dd, 1H), 6.73 (br s, 2H), 2.63 (d, 2H), 2.04-1.94 (m, 1H), 0.94 (d, 6H). LRMS [M+H]=252.1.

Workup

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

Sources & evidence

ORD record
ord-76d3fec7bedc43539d345557e211bf11
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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