Dimethylformamide → N-(2-Formylfuro[3,2-c]pyridin-4-yl)benzamide

HRID 1910660Notes

Reaction equation

HRID 1910660 reaction equation
[O:1]1[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([NH:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=[CH:2]1.C([Li])CCC.CN(C)[CH:26]=[O:27].[Cl-].[NH4+]>C1COCC1>[CH:26]([C:2]1[O:1][C:9]2[CH:8]=[CH:7][N:6]=[C:5]([NH:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1)=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 67154555N-(Furo[3,2-c]pyridin-4-yl)benzamideHCID 178418339Butyllithium

Product 1

HCID 86685438N-(2-Formylfuro[3,2-c]pyridin-4-yl)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.13 g (30 mmol) N-(Furo[3,2-c]pyridin-4-yl)benzamide (Example 2A) were dissolved in 150 ml dry THF under inert gas atmosphere. At −78° C., 26.4 ml (66 mmol) n-butyllithium solution (2.5 M in hexane) were added dropwise, and the mixture was stirred for 30 min at this temperature. Then, 5.1 ml (66 mmol) dry N,N-dimethylformamide were added dropwise. After addition was completed, the mixture was slowly warmed up to rt, and 300 ml saturated aq. ammonium chloride solution were added. After extraction with 300 ml diethyl ether, the organic phase was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford a brown solid. This material was purified by chromatography on silica gel (eluent dichloromethane/methanol 99:1 v/v) to afford 5.2 g (65% of th.) of the title compound as a pale yellow solid [cf. J. B. M. Rewinkel et al., Bioorg. Med. Chem. Lett. 9, 2837-2842 (1999)].

Workup

  1. additionAfter addition
  2. extractionAfter extraction with 300 ml diethyl ether
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford a brown solid
  7. customThis material was purified by chromatography on silica gel (eluent dichloromethane/methanol 99:1 v/v)

Sources & evidence

ORD record
ord-8cc9990dce374bf08ea613aed87ef809
Source dataset
uspto-grants-2013_12
Patent number
US08604028B2

Reaction notes

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