Ammonium Chloride → HCID 59177868, compound

HRID 1875434Notes

Reaction equation

HRID 1875434 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]([O:21][CH3:22])=[O:20].[Cl:23][C:24]1[C:25]([C:31](Cl)=[O:32])=[N:26][CH:27]=[C:28]([Cl:30])[CH:29]=1.[Cl-].[NH4+]>CCCCCC.C1COCC1.O>[Cl:23][C:24]1[C:25]([C:31](=[O:32])[CH:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[F:11])[C:19]([O:21][CH3:22])=[O:20])=[N:26][CH:27]=[C:28]([Cl:30])[CH:29]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 2733230Methyl 2-fluorophenylacetateHCID 2733832Lithium HexamethyldisilazideHCID 143689283,5-Dichloropyridine-2-carbonyl chloride

Product 1

HCID 59177868HCID 59177868, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

28.5 ml (28.5 mmol) of a 1 M solution of LiHMDS in hexane are added to 50 ml of THF at −78° C. A solution of 4.00 g (23.8 mmol) of methyl (2-fluorophenyl)acetate in 10 ml of THF is then added dropwise. The mixture is stirred at −78° C. for 1 h and then 6.00 g (28.5 mmol) of 3,5-dichloro-pyridine-2-carbonyl chloride are added in portions. After a further hour, the mixture is allowed to reach RT and saturated ammonium chloride solution is added dropwise. The mixture is diluted with water and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution and dried over sodium sulfate. The residue after concentration in vacuo is purified by chromatography on silica gel (eluent: dichloromethane/methanol 50:1). 4.46 g (46% of theory) of the desired compound are obtained as a yellowish oil.

Workup

  1. waitAfter a further hour
  2. customto reach RT
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe residue after concentration in vacuo
  7. customis purified by chromatography on silica gel (eluent: dichloromethane/methanol 50:1)

Sources & evidence

ORD record
ord-b43cd7f0f13b498a9ef821ad37f17307
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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