HCID 178461630, compound → HCID 178458546, compound

HRID 626194Notes

Reaction equation

HRID 626194 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[CH:4][N:3]=1.[CH3:14][CH2:15][Mg+].[Br-]>C1COCC1>[OH:1][C:2]1[N:3]=[CH:4][C:5]([C:6](=[O:7])[CH2:14][CH3:15])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 178461630HCID 178461630, compoundHCID 178502673HCID 178502673, compound

Product 1

HCID 178458546HCID 178458546, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-hydroxy-N-methoxy-N-methylnicotinamide (800 mg, 1.0 eq) in 20 mL anhydrous THF was added 3 M EtMgBr (6 mL, 4.0 eq) dropwise at 0° C. The reaction mixture was stirred at rt for 2 h., quenched with sat NH4Cl, and extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography to give the desired product (320 mg, 48%). 1H NMR (400 MHz, CDCl3) δ 12.13 (brs, 1H), 8.11 (d, J=2.4 Hz, 1H), 8.05 (dd, J=10.0 Hz, 2.8 Hz, 1H), 6.60 (d, J=9.6 Hz, 1H), 2.79 (q, J=7.2 Hz, 2H), 1.22 (t, J=7.2 Hz, 3H).

Workup

  1. customquenched with sat NH4Cl
  2. extractionextracted with CH2Cl2
  3. customThe extract was dried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-b72b9e812a32437290df56450a39c066
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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