Water → HCID 71271440, compound

HRID 1752488Notes

Reaction equation

HRID 1752488 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[CH:5].CCN(CC)CC.[CH3:13][O:14][C:15]([C:17]1[C:22]([NH2:23])=[CH:21][C:20](Br)=[CH:19][N:18]=1)=[O:16].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>[CH3:13][O:14][C:15]([C:17]1[C:22]([NH2:23])=[CH:21][C:20]([C:5]#[C:4][CH2:3][O:2][CH3:1])=[CH:19][N:18]=1)=[O:16]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 693933-MethoxypropyneHCID 50989141Methyl 3-amino-5-bromopyridine-2-carboxylate

Product 1

HCID 71271440HCID 71271440, 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 NEt3 (1.17 ml, 8.4 mmol) in THF (10 ml) under Argon was added 3-amino-5-bromo-pyridine-2-carboxylic acid methyl ester (277 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 combined organic layers were washed with half-saturated aq. sodium chloride, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1:4) to provide the title compound as orange solid.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washthe combined organic layers were washed with half-saturated aq. sodium chloride
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1:4)

Sources & evidence

ORD record
ord-56d172c170fd455c998a22fca5e8199a
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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