Potassium Carbonate → HCID 69621312, compound

HRID 1047172Notes

Reaction equation

HRID 1047172 reaction equation
F[C:2]1[N:24]=[C:23]([F:25])[C:22]([I:26])=[CH:21][C:3]=1[C:4]([C:6](=[CH:12][NH:13][C@@H:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:15][OH:16])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:25][C:23]1[N:24]=[C:2]2[C:3]([C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12][N:13]2[C@@H:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:15][OH:16])=[CH:21][C:22]=1[I:26]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178472054HCID 178472054, compound

Product 1

HCID 69621312HCID 69621312, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (5)-ethyl 2-(2,6-difluoro-5-iodonicotinoyl)-3-(1-hydroxy-3,3-dimethylbutan-2-ylamino)acrylate Intermediate 80 (4.47 g, 9.27 mmol, 1 equiv.) in DMF (46 mL) was added potassium carbonate (1.92 g, 13.9 mmol, 1.5 equiv.) was added, and the reaction was stirred at 70° C. for 30 min. The reaction was cooled to 0° C. and quenched with saturated ammonium chloride (5 mL). The reaction was partitioned between water (50 mL) and dichloromethane (50 mL). The aqueous layer was extracted with dichloromethane (2×30 mL), and the organics were concentrated. The compound was purified via silica gel chromatography and concentrated to afford (S)-ethyl 7-fluoro-1-(1-hydroxy-3,3-dimethylbutan-2-yl)-6-iodo-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate Intermediate 78 as a solid (3.37 g, 79%). Calcd for C17H26FIN2O4. H1NMR (d6-DMSO) δ 8.69 (s, 1H), 4.24 (m, 3H), 3.98 (m, 2H), 1.28 (t, 3H), 0.95 (s, 9H).

Workup

  1. additionwas added
  2. temperatureThe reaction was cooled to 0° C.
  3. customquenched with saturated ammonium chloride (5 mL)
  4. customThe reaction was partitioned between water (50 mL) and dichloromethane (50 mL)
  5. extractionThe aqueous layer was extracted with dichloromethane (2×30 mL)
  6. concentrationthe organics were concentrated
  7. customThe compound was purified via silica gel chromatography
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8738dc5cc2944b0fb4691306e4b30da7
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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