Potassium Carbonate → HCID 86695933, compound

HRID 870942Notes

Reaction equation

HRID 870942 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 C14H12ClN2O2 275.1] LC/MS retention time (method D): tR=1.77 min; 1H NMR (400 MHz, DMSO-d6) δ 10.6 (s, 1H), 8.41 (s, 1H), 8.25 (s, 1H), 7.78 (d, J=8.4 Hz, 1H), 7.22-7.15 (m, 2H), 5.2 (s, 2H), 2.2 (s, 3H).

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-3fe872a5f810431aa8b6e7c5ad55d5f9
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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