3,3-Dimethyl-1-butyne → HCID 59811264, compound

HRID 2113636Notes

Reaction equation

HRID 2113636 reaction equation
C[O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[N:6][CH:5]=1.C(N(CC)C(C)C)(C)C.[CH3:21][C:22]([CH3:26])([CH3:25])[C:23]#[CH:24]>O1CCOCC1.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.[Cu](I)I>[CH3:21][C:22]([CH3:26])([CH3:25])[C:23]#[C:24][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:11])=[CH:5][N:6]=1

Participants

7

Reactant 3

HCID 135123,3-Dimethyl-1-butyneHCID 81531DiisopropylethylamineHCID 254249Methyl 6-chloropyridine-3-carboxylate

Product 1

HCID 59811264HCID 59811264, compoundYield 99.1%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

6-Chloronicotinic acid methyl ester (500 mg; 2.93 mmol) was suspended in 1,4-dioxane (3 ml) in a 5 ml reaction vial. To the vessel was added dichlorobis(triphenylphosphine)palladium(II) (70 mg; 3 mol %), copper iodide (12 mg), N,N-diisopropylethylamine (0.63 ml; 3.5 mmol) and 3,3-dimethylbut-1-yne (0.44 ml; 3.5 mmol). The vessel was sealed and the mixture was heated at 80° C. for 24 hrs. The solvents were evaporated to dryness and 20 ml of tetrahydrofuran and 20 ml of 10N NaOH was added. The mixture was stirred at room temperature for 30 minutes and the solvent was evaporated. The basic layer was acidified with concentrated HCl and extracted three times with EtOAc. The organic layers were washed with brine and dried over Na2SO4, filtered and evaporated to give the desired product as a brown powder (590 mg; 99%).

Workup

  1. customThe vessel was sealed
  2. customThe solvents were evaporated to dryness and 20 ml of tetrahydrofuran and 20 ml of 10N NaOH
  3. additionwas added
  4. customthe solvent was evaporated
  5. extractionextracted three times with EtOAc
  6. washThe organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-bb5fa4432c714d8e894f3e73bcdc5b1a
Source dataset
uspto-grants-2008_10
Patent number
US07432281B2

Reaction notes

Loading…