Sodium hydride → 3-(benzhydrylideneamino)-6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one

HRID 18298

Reaction equation

[H-].[Na+].C(O[C:6](=[O:22])[CH2:7][N:8]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)C.Br.[NH2:24][C:25]1[C:30]([CH2:31]Br)=[CH:29][C:28]([Br:33])=[CH:27][N:26]=1>CN(C=O)C>[C:9](=[N:8][CH:7]1[CH2:31][C:30]2[C:25](=[N:26][CH:27]=[C:28]([Br:33])[CH:29]=2)[NH:24][C:6]1=[O:22])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

NaH (60% dispersion in mineral oil, 1.2 g, 30 mmole) was added portionwise over 10 min to a solution of N-(diphenylmethylene)glycine ethyl ester (8.0 g, 30 mmole) in DMF (150 mL) with stirring under Ar at 0° C. The reaction was stirred for 15 min, then 2-amino-5-bromo-3-(bromomethyl)pyridine hydrobromide (5.0 g, 14.4 mmole) was added in one portion. The reaction was allowed to warm to RT and stir for 18 h, then was concentrated under vacuum. The remaining residue was taken up in EtOAc (150 mL), hexane (150 mL), and H2O (150 mL). The resulting suspension was triturated and filtered, and the solid was dried under vacuum to give the title compound (3.27 g, 56%) as an off-white solid: 1H NMR (400 MHz, d6-DMSO) δ 10.92 (s, 1 H), 8.23 (s, 1 H), 7.86 (s, 1 H), 7.26-7.55 (m, 10H), 4.05 (dd, 1 H), 3.10 (t, 2 H); MS (ES) m/e 406.0 (M+H)+.

Workup

stirringThe reaction was stirred for 15 min
temperatureto warm to RT
stirringstir for 18 h
concentrationwas concentrated under vacuum
customThe resulting suspension was triturated
filtrationfiltered
customthe solid was dried under vacuum

Sources & evidence

ORD record: ord-54d91cc8f667456cb14f0403cd9bb788
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741339B2

Linked notes

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