3-Aminopyridine → 6-bromo-2-hydroxy-N-(pyridin-3-yl)quinoline-4-carboxamide

HRID 526071Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([OH:12])[CH:6]=[C:5]2[C:13]([OH:15])=O.[NH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.CCN(C(C)C)C(C)C>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([OH:12])[CH:6]=[C:5]2[C:13]([NH:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 6-bromo-2-hydroxyquinoline-4-carboxylic acid (9.0 g) was dissolved in dichloromethane and cooled to 0° C. 3-aminopyridine (1 eq), T3P (2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide, 50% solution in ethyl acetate, 1.2 eq.), and DIPEA (diisopropylethylamine, 2.0 eq) were added. The solution was stirred at 0° C. for 30 minutes and then allowed to warm to room temperature overnight. The solution was washed with water, sat. sodium chloride, dried, and concentrated. Purification by silica gel column chromatography provided 6-bromo-2-hydroxy-N-(pyridin-3-yl)quinoline-4-carboxamide (9.0 g).

Workup

temperatureto warm to room temperature overnight
washThe solution was washed with water, sat. sodium chloride
customdried
concentrationconcentrated
customPurification by silica gel column chromatography

Sources & evidence

ORD record: ord-977a796899514b2685cc56568cfd7e7e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345700B2

Reaction notes

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