Methanol → HCID 89649130, compound

HRID 2207652Notes

Reaction equation

HRID 2207652 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:21])=[C:8]([C:10]2[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[N:13]=[C:12]([C:19]#N)[CH:11]=2)[CH:9]=1)[CH3:2].[O:22]1CCOC[CH2:23]1.C[OH:29]>Cl>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:21])=[C:8]([C:10]2[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[N:13]=[C:12]([C:19]([O:22][CH3:23])=[O:29])[CH:11]=2)[CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 312751,4-DioxaneHCID 89649694HCID 89649694, compound

Product 1

HCID 89649130HCID 89649130, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4-(5-ethoxy-2-fluoro-phenyl)-6-isopropyl-pyridine-2-carbonitrile (which may be prepared as described in Description 114) (1.09 g, 3.8 mmol) in 4M HCl in dioxan (12 mL, 48 mmol) and methanol (12 mL) was heated to reflux under nitrogen overnight. The solvents were evaporated and ethyl acetate (150 ml) and NaHCO3 solution (150 ml) were added. The product was extracted into ethyl acetate (3 x) and the extracts were dried (Na2SO4) and concentrated. Chromatography (0-10% diethyl ether in DCM) gave methyl 4-(5-ethoxy-2-fluoro-phenyl)-6-isopropyl-pyridine-2-carboxylate (D115) (730.8 mg);

Workup

  1. temperatureto reflux under nitrogen overnight
  2. customThe solvents were evaporated
  3. additionethyl acetate (150 ml) and NaHCO3 solution (150 ml) were added
  4. extractionThe product was extracted into ethyl acetate (3 x)
  5. dry with materialthe extracts were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ea90dda6b5a943e5b7bcc1d48daf201a
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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