5-Bromo-2-methoxypyridine-3-carbaldehyde → HCID 58941096、化合物

HRID 506867ノート

反応式

HRID 506867 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31]P(=O)(OCC)OCC)=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].CC(C)([O-])C.[K+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:31]/[C:28]2[CH:27]=[CH:26][C:25]([N:22]3[CH2:21][CH2:20][N:19]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:24][CH2:23]3)=[CH:30][CH:29]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 15164035-Bromo-2-methoxypyridine-3-carbaldehydeHCID 23665647Potassium tert-butoxideHCID 58941093HCID 58941093、化合物

生成物 1

HCID 58941096HCID 58941096、化合物収率 83%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 5-bromo-2-methoxypyridine-3-carbaldehyde (1.5 g, 6.95 mmol) and diethyl (4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)methylphosphonate (2.39 g, 5.79 mmol) in anhydrous THF (50 mL) under nitrogen was added potassium tert-butoxide (1.30 g, 11.6 mmol) at rt over 5 min. After 3 h a further portion of the aldehyde (160 mg, 0.74 mmol) was added. After a further 30 min the reaction was concentrated and the residue purified by column chromatography (30% EtOAc in PE) to give the title compound (2.27 g, 83%) as a yellow oil. 1H NMR (CDCl3) 1.51 (9H, s), 3.24 (4H, t), 3.68 (4H, t), 4.00 (3H, s), 7.02 (2H, d), 7.11 (2H, m), 7.49 (2H, d), 7.89 (1H, s), 8.07 (1H, s).

後処理

  1. concentrationAfter a further 30 min the reaction was concentrated
  2. customthe residue purified by column chromatography (30% EtOAc in PE)

出典と根拠

ORDレコード
ord-647c92aebf054ee3a3dd9a8455ef7a9a
出典データセット
uspto-grants-2010_08
特許番号
US07786120B2

反応ノート

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