Triethylamine → Ethyl 4-(2-aminopyridin-6-ylethynyl)benzoate

HRID 583702

Reaction equation

HRID 583702 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.[CH2:9]([O:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[CH:15][CH:14]=1)[CH3:10].CCN(CC)CC>CC#N.CCOC(C)=O.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>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:20]#[C:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]([O:11][CH2:9][CH3:10])=[O:21])=[CH:14][CH:15]=2)[N:3]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 3008092-Amino-6-bromopyridineHCID 15540683Ethyl 4-ethynylbenzoate

Product 1

HCID 10683170Ethyl 4-(2-aminopyridin-6-ylethynyl)benzoate

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-6-bromopyridine (0.38 g, 2.4 mmol), alkyne 29-2 (0.35 g, 2.0 mmol), Et3N (1.0 mL, 7.2 mmol), (Ph3P)2PdCl2 (76 mg, 0.11 mmol), an CuI (26 mg, 0.14 mmol) were combined in 5 mL CH3CN, sealed in a glass pressure tube and heated to 100° for 3 h. The mixture was diluted with EtOAc, washed with water and brine, dried (MgSO4), concentrated, and purified by flash chromatography (silica, 5% acetone/hexane), to give 29-3 as a tan solid.

Workup

  1. customsealed in a glass pressure tube
  2. temperatureheated to 100° for 3 h
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by flash chromatography (silica, 5% acetone/hexane)

Sources & evidence

ORD record
ord-4a1cc6d752804f3ca40eba6af34d2b96
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Linked notes

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