5-Bromo-2-methoxypyridine-3-carbaldehyde → HCID 58941096, 화합물

HRID 506867노트

반응식

HRID 506867 반응식
[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

참가 물질

5

반응물 3

HCID 15164035-Bromo-2-methoxypyridine-3-carbaldehydeHCID 23665647Potassium tert-butoxideHCID 58941093HCID 58941093, 화합물

생성물 1

HCID 58941096HCID 58941096, 화합물수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-647c92aebf054ee3a3dd9a8455ef7a9a
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786120B2

반응 노트

불러오는 중…