Ammonium Chloride → HCID 67183864, compound

HRID 1843636Notes

Reaction equation

HRID 1843636 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].C([O:26][C:27](=O)[C:28]1[C:33]([F:34])=[CH:32][CH:31]=[C:30]([N:35]([CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:29]=1[F:50])C1C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1>[CH2:43]([N:35]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:30]1[C:29]([F:50])=[C:28]([C:27](=[O:26])[CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=2)[C:33]([F:34])=[CH:32][CH:31]=1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27374032-Fluoro-4-methylpyridineHCID 584771183-Dibenzylamino-2,6-difluoro-benzoic acid benzyl ester

Product 1

HCID 67183864HCID 67183864, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-fluoro-4-methyl-pyridine (5.76 mL, 0.056 mol) in anhydrous tetrahydrofuran (200 mL) at 0° C. sodium hexamethyldisilazide (NaHMDS, 2 M in tetrahydrofuran, 36 mL, 0112 mol) was added and the reaction was stirred for 1 hour. A solution of 3-dibenzylamino-2,6-difluoro-benzoic acid benzyl ester (25 g, 0.056 mol) in tetrahydrofuran (80 mL) was then added dropwise to the reaction mixture, which was stirred at 0° C. for one hour and allowed to warm at room temperature. The reaction mixture was then poured into saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified by silica gel column chromatography eluting with ethyl acetate 15% in hexane (40.7%).

Workup

  1. stirringwas stirred at 0° C. for one hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by silica gel column chromatography
  8. washeluting with ethyl acetate 15% in hexane (40.7%)

Sources & evidence

ORD record
ord-02311ee2bd07485997b1e66e9f84d480
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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