Ammonium Chloride → HCID 67987827, compound

HRID 1748498Notes

Reaction equation

HRID 1748498 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][O:12][C:13]([CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14].[Br:21][C:22]1[CH:23]=[CH:24][C:25](F)=[N:26][CH:27]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:11][O:12][C:13]([C:15]1([C:25]2[CH:24]=[CH:23][C:22]([Br:21])=[CH:27][N:26]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl esterHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 67987827HCID 67987827, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.0 M Tetrahydrofuran solution (28 ml) of lithium bis(trimethylsilyl)amide was added dropwise to a solution of tetrahydro-2H-pyrane-4-carboxylic acid methyl ester (2.87 g) in tetrahydrofuran (40 ml) at −78° C., and the mixture was stirred at the same temperature for an hour. And then a solution of 5-bromo-2-fluoropyridine (3.5 g) was added dropwise, and the reaction mixture was stirred at room temperature for two hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 4-(5-bromopyridin-2-yl)tetrahydro-2H-pyrane-4-carboxylic acid methyl ester (4.14 g) as a colorless oil.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for two hours
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f44fc997df2845b98ec781c40112b0b1
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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