Potassium Carbonate → HCID 87918846, compound

HRID 1047175Notes

Reaction equation

HRID 1047175 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]([CH2:12][C@H:13]1[CH2:17][CH2:16][NH:15][CH2:14]1)[CH:7]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5]2=[O:23].I[CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]([CH2:12][C@H:13]1[CH2:17][CH2:16][N:15]([CH2:25][CH2:26][CH3:27])[CH2:14]1)[CH:7]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5]2=[O:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 87918850HCID 87918850, compound

Product 1

HCID 87918846HCID 87918846, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (5)-ethyl 6-bromo-4-oxo-1-(pyrrolidin-3-ylmethyl)-1,4-dihydro-1,7-naphthyridine-3-carboxylate Intermediate 94 (511.5 mg, 1.2 mmol, 1 equiv.) in acetonitrile (3 mL) and DMF (1 mL) was added iodopropane (0.234 mL, 2.4 mmol, 2 equiv.) followed by potassium carbonate (663 mg, 4.8 mmol, 4 equiv.). The reaction was stirred at 60° C. for 2 days. The reaction was cooled to 23° C. and concentrated. The residue was re-suspended and partitioned between ethyl acetate (10 mL) and water (10 mL). The aqueous layer was extracted with ethyl acetate (2×10 mL), and the organics were dried and concentrated to afford (S)-ethyl 6-bromo-4-oxo-1-((1-propylpyrrolidin-3-yl)methyl)-1,4-dihydro-1,7-naphthyridine-3-carboxylate (211 mg, 38%). Calcd for C19H24BrN3O3 [M+H]+: 424.0.

Workup

  1. temperatureThe reaction was cooled to 23° C.
  2. concentrationconcentrated
  3. custompartitioned between ethyl acetate (10 mL) and water (10 mL)
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  5. customthe organics were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5e7d64e5c1bb43598fa325ca3f6378af
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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