Hydrochloric Acid → HCID 53434041, compound

HRID 2358255Notes

Reaction equation

HRID 2358255 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[F:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][N:13]=1.[Br:19][C:20]1[CH:30]=[CH:29][C:23]([C:24](OCC)=[O:25])=[CH:22][CH:21]=1.Cl.[OH-].[Na+]>C1COCC1>[Br:19][C:20]1[CH:30]=[CH:29][C:23]([C:24](=[O:25])[CH2:18][C:16]2[CH:15]=[CH:14][N:13]=[C:12]([F:11])[CH:17]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22043Ethyl 4-bromobenzoateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27374032-Fluoro-4-methylpyridine

Product 1

HCID 53434041HCID 53434041, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sodium bis(trimethylsilyl)amide (235 mL, 2M) in THF (750 mL) under nitrogen, cooled to 2° C., was added 2-fluoro-4-methylpyridine (25 g, 0.225 mol) and the solution stirred for 45 minutes in an ice bath. Ethyl 4-bromobenzoate (55 g, 0.239 mol) was added and the reaction was stirred overnight at RT. The reaction mixture was poured into excess aqueous 2N HCl, and the aqueous layer was made basic with 5 N NaOH and extracted with EtOAc. The organic extracts were combined, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was dissolved in CH2Cl2 and filtered through a cotton plug. Hexanes were added and the CH2Cl2 was removed under reduced pressure until precipitation of the title compound occurred as a pale yellow solid. 1H NMR (400 MHz, CDCl3): δ8.20 (m, 1H), 7.85 (m, 2H), 7.65 (m, 2H), 7.05 (m, 1H), 6.82 (m, 1H), 4.30(s, 2H).

Workup

  1. stirringthe reaction was stirred overnight at RT
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in CH2Cl2
  8. filtrationfiltered through a cotton plug
  9. additionHexanes were added
  10. customthe CH2Cl2 was removed under reduced pressure until precipitation of the title compound

Sources & evidence

ORD record
ord-fe96d6e47f854ecabcc5a512d54ece94
Source dataset
uspto-grants-2010_07
Patent number
US07763634B2

Reaction notes

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