Water → HCID 58286923, compound

HRID 1962394Notes

Reaction equation

HRID 1962394 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][C:12](=O)[CH3:13])[C:3]=1[C:4]([OH:6])=O.[NH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.O>O1CCOCC1>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:6])[N:15]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[C:12]([CH3:13])=[CH:11]2

Participants

5

Reactant 3

HCID 962WaterHCID 100093-AminopyridineHCID 58286932HCID 58286932, compound

Product 1

HCID 58286923HCID 58286923, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Fluoro-6-(2-oxo-propyl)-benzoic acid (12.33 g, 31.43 mmol) and 3-aminopyridine (5.12 g, 54.4 mmol) in 25 mL dioxane were refluxed overnight. The reaction mixture was poured into water (250 mL). The mixture was extracted with ethyl acetate (200 mL). The organic phase was washed with brine, dried over MgSO4 and filtered through a pad of silica gel. The silica gel pad was washed with 250 mL ethyl acetate. The organic fractions were combined and rotavaped. The crude product was flash chromatographed on silica gel (eluent: 50% heptane/ethyl acetate to ethyl acetate) to obtain the product as a pale pink solid (1.3 g, yield 16.3%). LC-MS (m/z) 255.5 (MH+); tR=0.64. 1H NMR (500 MHz, CDCl3): 1.99 (s, 3H, Me), 6.43 (s, 1H), 7.07 (dd, J=8.12 Hz, J=11.3 Hz, 1H), 7.24 (d, J=7.9 Hz, 1H), 7.49 (dd, J=4.9 Hz, J=8.1 Hz, 1H), 7.58 (td, J(d)=4.8 Hz, J(t)=8 Hz, 1H), 7.64 (unresolved dt, J(d)=8.1 Hz, J(t)=ca. 1.5 Hz, 1H), 8.53 (d, J=2 Hz, 1H), 8.71 (d, J=4.8 Hz, J=0.9 Hz, 1H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (200 mL)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered through a pad of silica gel
  5. washThe silica gel pad was washed with 250 mL ethyl acetate
  6. customchromatographed on silica gel (eluent: 50% heptane/ethyl acetate to ethyl acetate)

Sources & evidence

ORD record
ord-9021d6c4d0e64f6ca4b2d82c7dc63a73
Source dataset
uspto-grants-2013_04
Patent number
US08415356B2

Reaction notes

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