(Cyclopropylmethyl)triphenylphosphonium bromide → 8-(2-Cyclopropylethyl)benzo[f][1,7]naphthyridin-5-amine

HRID 340320Notes

Reaction equation

HRID 340320 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]1([CH2:22][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:21][CH2:20]1>>[CH:19]1([CH2:22][CH2:16][C:14]2[CH:13]=[CH:12][C:5]3=[C:6]4[C:11](=[C:2]([NH2:1])[N:3]=[C:4]3[CH:15]=2)[N:10]=[CH:9][CH:8]=[CH:7]4)[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 3084208(Cyclopropylmethyl)triphenylphosphonium bromideHCID 866523555-Aminobenzo[f][1,7]naphthyridine-8-carbaldehyde

Product 1

HCID 582137888-(2-Cyclopropylethyl)benzo[f][1,7]naphthyridin-5-amine

Procedure

8-(2-Cyclopropylethyl)benzo[f][1,7]naphthyridin-5-amine was prepared from 5-aminobenzo[f][1,7]naphthyridine-8-carbaldehyde (from Example 87) with (cyclopropylmethyl)triphenylphosphonium 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), 7.47 (d, 1H), 7.23 (dd, 1H), 6.64 (br s, 2H), 1.60 (q, 2H), 1.34-1.25 (m, 1H), 0.91-0.72 (m, 2H), 0.45-0.41 (m, 2H), 0.11-0.07 (m, 2H). LRMS [M+H]=264.1.

Workup

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

Sources & evidence

ORD record
ord-527a1feb2c4b43f5acc4842748ff042b
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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