HCID 86680613, compound → HCID 86680614, compound

HRID 1497440Notes

Reaction equation

HRID 1497440 reaction equation
[CH:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=[O:2].[CH2:18]([Mg]Br)[CH3:19]>C1COCC1.C(OCC)(=O)C>[OH:2][CH:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH2:18][CH3:19]

Participants

5

Reactant 2

HCID 86680613HCID 86680613, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 86680614HCID 86680614, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(6-formylpyridin-3-yl)benzamide (0.30 g, 1.32 mmol), in THF (30 mL) was added ethyl magnesium bromide (0.53 g, 3.97 mmol, 3M in diethyl ether) under nitrogen at 0° C. and the contents were stirred for 3 h at the same temperature. The contents were diluted with ethyl acetate (150 mL), quenched with ammonium chloride solution (100 mL), the organic layer washed with brine solution (2×100 mL), the layers separated, the organic layer dried over sodium sulphate and distilled off to get the crude product. The compound was purified by flash chromatography (100-200 micron; 60% ethyl acetate in hexane) to give 4-(6-(1-hydroxypropyl)pyridin-3-yl)benzamide (0.17 g, 51% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.83 (s, 1H), 8.10 (dd, 1H), 8.00 (s, 1H), 7.97 (d, 2H), 7.79 (d, 2H), 7.55 (d, 1H), 7.36 (s, 1H), 5.30 (d, 1H), 4.53 (q, 1H), 1.17 (m, 1H), 1.65 (m, 1H), 0.86 (t, 3H); LC-MS m/z calcd for [M+H]+ 257.31. found 257.4.

Workup

  1. customquenched with ammonium chloride solution (100 mL)
  2. washthe organic layer washed with brine solution (2×100 mL)
  3. customthe layers separated
  4. dry with materialthe organic layer dried over sodium sulphate
  5. distillationdistilled off
  6. customto get the crude product
  7. customThe compound was purified by flash chromatography (100-200 micron; 60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9e365a47f0ae4670811e9227aca4f504
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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