Potassium Carbonate → HCID 86695933, compound

HRID 2369532Notes

Reaction equation

HRID 2369532 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH2:14][OH:15])=[CH:12][N:11]=[C:10]([NH:16][C:17](=[O:19])[CH3:18])[CH:9]=2)=[C:4](F)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:13](=[CH:12][N:11]=[C:10]([NH:16][C:17](=[O:19])[CH3:18])[CH:9]=3)[CH2:14][O:15][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86695934HCID 86695934, compound

Product 1

HCID 86695933HCID 86695933, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of N-(4-(4-chloro-2-fluorophenyl)-5-(hydroxymethyl)pyridin-2-yl)acetamide (9 g, 23.82 mmol) in DMF (90 mL) was added potassium carbonate (9.88 g, 71.5 mmol) and the resultant mixture was sealed tightly and heated at 95° C. for 16 h. The reaction mixture was then cooled to room temperature and volatiles were removed under reduced pressure. The crude material was taken up in water (200 mL) and filtered. The residue was washed with water (2×250 mL) and dried under reduced pressure for 16 h to afford N-(8-chloro-5H-chromeno[3,4-c]pyridin-2-yl)acetamide (5.5 g, 20.02 mmol, 84% yield) as a pale brown solid. LCMS (ESI) m/e 275.2 [(m)−, calcd for C14H12ClN2O2275.1] LC/MS retention time (method D): tR=1.77 min; 1H NMR (400 MHz, DMSO-d6) δ 10.6 (s, 1 H), 8.41 (s, 1 H), 8.25 (s, 1 H), 7.78 (d, J=8.4 Hz, 1 H), 7.22-7.15 (m, 2 H), 5.2 (s, 2 H), 2.2 (s, 3 H).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customvolatiles were removed under reduced pressure
  3. filtrationfiltered
  4. washThe residue was washed with water (2×250 mL)
  5. customdried under reduced pressure for 16 h

Sources & evidence

ORD record
ord-a103a95a71664db7b8eeb2b8ae181a08
Source dataset
uspto-grants-2014_04
Patent number
US08703953B2

Reaction notes

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