Diethyl Ether → HCID 86680611, compound

HRID 1497437Notes

Reaction equation

HRID 1497437 reaction equation
[CH:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([NH:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=[O:2].[CH2:19]([Mg]Br)[CH3:20].C(OCC)C.CO.C(Cl)Cl>C1COCC1>[OH:2][CH:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([NH:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 21226129Dichloromethane methanolHCID 86680610HCID 86680610, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 86680611HCID 86680611, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(6-formylpyridin-3-yl)-N-methylbenzamide (0.2 g, 0.8 mmol) in THF (15 mL) at −30° C. was slowly added 3.0 M ethyl magnesium bromide in diethyl ether (0.9 mL, 2.4 mmol) and the reaction mixture was stirred at rt for 3 h. After completion of the reaction as monitored with TLC (5% MeOH\DCM), the reaction mixture was quenched with sat'd. NH4Cl (50 mL) solution. The reaction mixture was extracted with EtOAc (3×50 mL), washed with water (2×50 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel 230-400μ) using 2% methanol in dichloromethane. The product was isolated as a yellow solid (0.1 g, 45% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.82 (d, 1H), 8.46 (d, 1H), 8.11 (dd, 1H), 7.92 (d, 2H), 7.80 (d, 2H), 7.51 (d, 1H), 5.30 (d, 1H), 4.54 (q, 1H), 2.78 (d, 3H), 1.79 (m, 1H), 1.63 (m, 1H), 0.85 (t, 3H).

Workup

  1. customat −30° C.
  2. customAfter completion of the reaction
  3. customthe reaction mixture was quenched with sat'd
  4. extractionThe reaction mixture was extracted with EtOAc (3×50 mL)
  5. washwashed with water (2×50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by column chromatography (silica gel 230-400μ)

Sources & evidence

ORD record
ord-2346282407b54c00b4aa57b747d5c4d9
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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