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

HRID 506867Notes

Reaction equation

HRID 506867 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 58941096HCID 58941096, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-647c92aebf054ee3a3dd9a8455ef7a9a
Source dataset
uspto-grants-2010_08
Patent number
US07786120B2

Reaction notes

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