Triethylamine → HCID 178522902, compound

HRID 2289959Notes

Reaction equation

HRID 2289959 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18](I)=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1.[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)#[CH:26].CCN(CC)CC>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([C:26]#[C:25][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 137268EthynylpyridineHCID 178522917HCID 178522917, compound

Product 1

HCID 178522902HCID 178522902, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the title compound of Example 5 (540.3 mg), 2-ethynyl pyridine (0.172 g), PdCl2 (PPh3)2 (21.1 mg), and 0.75 mL Et3N in 3 mL DMF is heated at 90° C. for 1 hr. The reaction mixture is cooled to room temperature and diluted with H2O. A tan solid precipitates, which is collected, dissolved in a mixture of CH2Cl2 and MeOH, and adsorbed onto silica. The crude product is chromatographed eluting with 2% MeOH in CH2Cl2. Fractions homogenous by TLC are combined, condensed and recrystallized from hot MeOH/CH2Cl2 and hexanes to yield 0.302 g of the desired product as a white solid.

Workup

  1. customA tan solid precipitates
  2. customwhich is collected
  3. dissolutiondissolved in a mixture of CH2Cl2 and MeOH
  4. customThe crude product is chromatographed
  5. washeluting with 2% MeOH in CH2Cl2
  6. customcondensed
  7. customrecrystallized from hot MeOH/CH2Cl2 and hexanes

Sources & evidence

ORD record
ord-8c6ef6a6fd73479895bce6a6c7d6b6b8
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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