N-methyl-2-pyrrolidone → HCID 89649694, compound

HRID 2207651Notes

Reaction equation

HRID 2207651 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[CH:13]=[CH:12][C:11]=2[F:19])[CH:3]=1.CN1C(=O)[CH2:24][CH2:23][CH2:22]1.C([Mg]Cl)(C)C>C1COCC1.CCOCC>[CH2:17]([O:16][C:14]1[CH:13]=[CH:12][C:11]([F:19])=[C:10]([C:4]2[CH:3]=[C:2]([CH:23]([CH3:24])[CH3:22])[N:7]=[C:6]([C:8]#[N:9])[CH:5]=2)[CH:15]=1)[CH3:18]

Participants

6

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 89648832HCID 89648832, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 89649694HCID 89649694, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 6-chloro-4-(5-ethoxy-2-fluoro-phenyl)pyridine-2-carbonitrile (which may be prepared as described in Description 113) (1.5 g, 5.42 mmol) NMP (2.61 mL, 27.07 mmol) and Fe(acac)3 (95.73 mg, 0.2700 mmol) in THF (27.106 mL) was stirred at 0° C. and treated with 2M isopropyl magnesium chloride in THF (7.59 mmol) and the mixture was stirred at 0° C. for 30 mins. The mixture was diluted with ether (200 ml) and quenched with brine. The product was extracted into ether (3x) and the extracts were dried (Na2SO4) and evaporated. The product was purified by flash chromatography (0-100% DCM in isohexane) to give 4-(5-ethoxy-2-fluoro-phenyl)-6-isopropyl-pyridine-2-carbonitrile (D114) as a white solid;

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 mins
  2. customquenched with brine
  3. extractionThe product was extracted into ether (3x)
  4. dry with materialthe extracts were dried (Na2SO4)
  5. customevaporated
  6. customThe product was purified by flash chromatography (0-100% DCM in isohexane)

Sources & evidence

ORD record
ord-2cc45c1404bb4e039827dc8539ea6e4e
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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