Potassium Carbonate → HCID 86590134, compound

HRID 1840521Notes

Reaction equation

HRID 1840521 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][C:12]([CH3:26])([O:14][C:15]([NH:17][C@@H:18]([CH2:23][C:24]#[CH:25])[C:19]([O:21][CH3:22])=[O:20])=[O:16])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:13][C:12]([CH3:26])([O:14][C:15]([NH:17][C@@H:18]([CH2:23][C:24]#[C:25][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[C:19]([O:21][CH3:22])=[O:20])=[O:16])[CH3:11]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 782402-Bromo-5-nitropyridineHCID 11817013(S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoate

Product 1

HCID 86590134HCID 86590134, compoundYield 65%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-bromo-5-nitropyridine (10.0 g; 49.0 mmol), methyl (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]pent-4-ynoate (13.34 g; 58.8 mmol), copper iodide (0.465 g; 2.5 mmol), potassium carbonate (13.6 g; 98.0 mmol) and dichlorobis(triphenylphosphine)palladium (1.7 g; 2.5 mmol) in 30 ml of anhydrous dimethylformamide (DMF) is heated for 4 hours at 60° C. under argon. The reaction mixture is taken up in 800 ml of ethyl acetate, washed with 2×400 ml of water, 400 ml of saturated hydrogen carbonate and 400 ml of brine, dried over sodium sulphate, filtered and then concentrated under reduced pressure. The residue obtained is purified on a column of silica, eluting with a cyclohexane/ethyl acetate gradient of from 0 to 20% ethyl acetate. 11 g of methyl (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(5-nitropyrid-2-yl)pent-4-ynoate is isolated.

Workup

  1. washwashed with 2×400 ml of water, 400 ml of saturated hydrogen carbonate and 400 ml of brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customis purified on a column of silica
  7. washeluting with a cyclohexane/ethyl acetate gradient of from 0 to 20% ethyl acetate

Sources & evidence

ORD record
ord-faa9066029644151b344ebe3cf4afd74
Source dataset
uspto-grants-2004_01
Patent number
US06680329B2

Reaction notes

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