3-Fluorobenzylamine → 3-[(3-Fluorobenzyl)amino]pyridine-4-carboxylic acid

HRID 63033Notes

Reaction equation

HRID 63033 reaction equation
F[C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][NH2:16]>CC(N(C)C)=O>[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][NH:16][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 668533-FluorobenzylamineHCID 3453613-Fluoropyridine-4-carboxylic acid

Product 1

HCID 817504513-[(3-Fluorobenzyl)amino]pyridine-4-carboxylic acidYield 33.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
168 °C

Procedure

3-Fluoroisonicotinic acid (100 mg, 0.71 mmol) and 3-fluorobenzylamine (308 μL, 2.84 mmol) were combined in DMA (3 mL) and the solution was stirred at 168° C. in a microwave for 90 min. The solution was concentrated in vacuo and purified through a short plug of silica gel chromatography (20% MeOH/DCM). The semi-pure fractions were concentrated and then taken up in water to give a white precipitate, which was collected by filtration and dried under vacuum to give 58 mg (33%) of the title compound. 1H NMR (500 MHz, DMSO-d6): δ 8.18 (s, 1H), 7.99 (br s, 1H), 7.84 (d, 1H, J=5.0 Hz), 7.58 (d, 1H, J=5.0 Hz), 7.31-7.41 (m, 2H), 7.15-7.23 (m, 2H), 4.62 (s, 2H). [M+H] calc'd for C13H11FN2O2, 247. found 247.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified through a short plug of silica gel chromatography (20% MeOH/DCM)
  3. concentrationThe semi-pure fractions were concentrated
  4. customto give a white precipitate, which
  5. filtrationwas collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-bd4108fd0b7c47ab8edb27d4df4f389e
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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