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

HRID 18298

反応式

HRID 18298 の反応式
[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

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

生成物 1

HCID 221391353-(benzhydrylideneamino)-6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one収率 56%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

  1. stirringThe reaction was stirred for 15 min
  2. temperatureto warm to RT
  3. stirringstir for 18 h
  4. concentrationwas concentrated under vacuum
  5. customThe resulting suspension was triturated
  6. filtrationfiltered
  7. customthe solid was dried under vacuum

出典と根拠

ORDレコード
ord-54d91cc8f667456cb14f0403cd9bb788
出典データセット
uspto-grants-2010_06
特許番号
US07741339B2

関連ノート

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