Water → HCID 71271169, compound

HRID 1752491Notes

Reaction equation

HRID 1752491 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[CH:5].C[O:7][C:8]([C:10]1[C:15]([Cl:16])=[CH:14][C:13](Br)=[CH:12][N:11]=1)=[O:9].O>C1COCC1.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>[Cl:16][C:15]1[C:10]([C:8]([OH:9])=[O:7])=[N:11][CH:12]=[C:13]([C:5]#[C:4][CH2:3][O:2][CH3:1])[CH:14]=1

Participants

7

Reactant 3

HCID 962WaterHCID 693933-MethoxypropyneHCID 46311201Methyl 5-bromo-3-chloropyridine-2-carboxylate

Product 1

HCID 71271169HCID 71271169, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-methoxy-propyne (421 mg, 6 mmol), bis(triphenylphosphine)palladium(II) chloride (84 mg, 0.12 mmol), copper(I) iodide (23 mg, 0.12 mmol) and N Eta (1.17 ml, 8.4 mmol) in THF (10 ml) under Argon was added 3-chloro-5-bromo-pyridine-2-carboxylic acid methyl ester (284 mg, 1.2 mmol) and the mixture was heated to 80° C. for 5 h. At 0° C. water (12 ml) was added and the mixture was extracted with EtOAc. The aq. Phase was acidified to pH 1 by addition of 1N HCl, extracted with DCM. The combined DCM extracts were washed with half-saturated aq. sodium chloride, dried with Na2SO4 and evaporated to provide the title compound as an off-white solid, which was used for coupling reactions without further purification.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. additionThe aq. Phase was acidified to pH 1 by addition of 1N HCl
  3. extractionextracted with DCM
  4. washThe combined DCM extracts were washed with half-saturated aq. sodium chloride
  5. dry with materialdried with Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-c636506c24b544f7a3bbff736b54783d
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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