Triethylamine → HCID 178494888, compound

HRID 2289961Notes

Reaction equation

HRID 2289961 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.[CH2:25]([O:28][CH3:29])[C:26]#[CH:27].CCN(CC)CC>CN(C=O)C.CO>[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:27]#[C:26][CH2:25][O:28][CH3:29])=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 693933-MethoxypropyneHCID 178522917HCID 178522917, compound

Product 1

HCID 178494888HCID 178494888, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the title compound of Example 5 (540.3 mg), methyl propargyl ether (0.14 mL), 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 partitioned between EtOAc and H2 0. The aqueous layer is washed with EtOAc (4×). The combined organic layers are dried over Na2SO4 and condensed to obtain a dark residue. The residue is diluted with MeOH, adsorbed onto silica, and chromatographed eluting with 2% MeOH in CH2Cl2. Fractions homogenous by TLC are combined, condensed and recrystallized from EtOAc/hexanes to yield 0.218 g of the desired product as a white solid.

Workup

  1. custompartitioned between EtOAc and H2 0
  2. washThe aqueous layer is washed with EtOAc (4×)
  3. dry with materialThe combined organic layers are dried over Na2SO4 and condensed
  4. customto obtain a dark residue
  5. customchromatographed
  6. washeluting with 2% MeOH in CH2Cl2
  7. customcondensed
  8. customrecrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-1f44bf44ff3a4d8ca711c18710eea2b3
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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