3-Pyridinylboronic acid → 6-Pyridin-3-yl-3,4-dihydro-1H-[1,5]naphthyridin-2-one

HRID 1774801Notes

Reaction equation

HRID 1774801 reaction equation
CO[C:3](=[O:26])[CH2:4][CH:5]([C:16]1[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[C:18](Br)[N:17]=1)S(C1C=CC(C)=CC=1)(=O)=O.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29](B(O)O)[CH:28]=1>>[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:18]2[N:17]=[C:16]3[C:21](=[CH:20][CH:19]=2)[NH:22][C:3](=[O:26])[CH2:4][CH2:5]3)[CH:28]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 866791573-(6-Bromo-3-nitro-pyridin-2-yl)-3-(toluene-4-sulfonyl)-propionic acid methyl ester

Product 1

HCID 715334496-Pyridin-3-yl-3,4-dihydro-1H-[1,5]naphthyridin-2-one

Procedure

In analogy to the procedures described for the preparation of example 32 (steps [C] to [D]), the title compound was prepared using 3-(6-bromo-3-nitro-pyridin-2-yl)-3-(toluene-4-sulfonyl)-propionic acid methyl ester and 3-pyridine boronic acid as corresponding starting materials. MS: 226.1 (M+H+).

Workup

  1. customIn analogy to the procedures described for the preparation of example 32 (steps [C] to [D])

Sources & evidence

ORD record
ord-c0b59bad6af34ea799db5ce8e0aefd33
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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