Dimethylformamide → HCID 58094897, compound

HRID 2402467Notes

Reaction equation

HRID 2402467 reaction equation
[H-].[Na+].CN(C)C=O.[Br:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:10]=1.[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1>CCOC(C)=O.CCCCCC>[Br:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([N:15]([CH2:25][C:24]2[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)[C:16](=[O:18])[CH3:17])[CH:10]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 59529635N-(4-Bromopyridin-2-yl)acetamide

Product 1

HCID 58094897HCID 58094897, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a 20 mL vial charged with Sodium hydride (0.196 g, 7.76 mmol) was added dry N,N-Dimethylformamide (5.0 mL, 64 mmol), cooled with ice bath. N-(4-bromopyridin-2-yl)acetamide (1.50 g, 7.00 mmol) was added portionwise in ˜3 min. The suspension was stirred at the same temperature for 15 min and turned into a clear solution. 4-methoxybenzyl bromide (1.55 g, 7.70 mmol) was added dropwise with a syringe and rinsed down with dry N,N-Dimethylformamide (2.0 mL, 26 mmol). The mixture was stirred at r.t. for 17 hours. The mixture was poured into ice chilled saturated NaHCO3 (80 mL), extracted with EtOAc (2×100 mL), washed with water, brine, dried over anhydrous Na2SO4, filtered, evaporated in rotavpor to give a crude. Chromatograph using EtOAc/hexane (1/9 to 7/3) gave an oily product (1.80 g, yield 76.7%). LCMS: (AA) ES+, 335, 337. 1H NMR (400 MHz, d1-chloroform) δ: 8.28-8.30 (d, J=5.27 Hz, 1H), 7.43 (s, 1H), 7.31-7.33 (dd, J=5.52, 1.51 Hz, 1H), 7.13-7.15 (d, J=8.78 Hz, 2H), 6.80-6.82 (d, J=8.78 Hz, 2H), 5.05 (s, 2H), 3.77 (s, 3H), 2.12 (s, 3H).

Workup

  1. temperaturecooled with ice bath
  2. stirringThe mixture was stirred at r.t. for 17 hours
  3. extractionextracted with EtOAc (2×100 mL)
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated in rotavpor
  8. customto give a crude

Sources & evidence

ORD record
ord-a52c3f08c5ff490c8b789ab56e71ea1b
Source dataset
uspto-grants-2014_08
Patent number
US08796314B2

Reaction notes

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