Ammonium Chloride → HCID 86692510, compound

HRID 1748564Notes

Reaction equation

HRID 1748564 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Br:21][C:22]1[CH:23]=[C:24]([CH3:29])[C:25](F)=[N:26][CH:27]=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1.O1CCCC1>[CH3:1][O:2][C:3]([C:5]1([C:25]2[C:24]([CH3:29])=[CH:23][C:22]([Br:21])=[CH:27][N:26]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl esterHCID 120569025-Bromo-2-fluoro-3-methylpyridine

Product 1

HCID 86692510HCID 86692510, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tetrahydro-2H-pyran-4-carboxylic acid methyl ester (759 mg) in toluene (5 ml) was added dropwise a 1.0 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (5.26 ml) under ice-cooling, and stirred at the same temperature for 1 hour. Then, a solution of 5-bromo-2-fluoro-3-methylpyridine (1 g) in toluene (5 ml) was added dropwise thereto, and stirred at room temperature for 2 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added thereto, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 4-(5-bromo-3-methylpyridin-2-yl)tetrahydro-2H-pyran-4-carboxylic acid methyl ester (753 mg) as a pale yellow oil. MS (ESI) m/z: 314, 316 (M+H)+.

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature for 2 hours
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5dba258b31b243f9b7d40b181b6a852d
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

Loading…