Triethylamine → HCID 178522903, compound

HRID 2289970Notes

Reaction equation

HRID 2289970 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]([OH:30])[CH2:26][CH2:27][C:28]#[CH:29].CCN(CC)CC>CN(C=O)C.C(Cl)Cl>[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:29]#[C:28][CH2:27][CH2:26][CH2:25][OH:30])=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 793464-Pentyn-1-olHCID 178522917HCID 178522917, compound

Product 1

HCID 178522903HCID 178522903, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the title compound of Example 5 (540.3 mg), 4-pentyn-1-ol (0.16 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 H2O. The aqueous layer is washed with EtOAc (3×). The combined organic layers are dried over Na2SO4 and condensed to obtain a red-brown residue. The residue is diluted with CH2Cl2 and chromatographed eluting with 2% MeOH in CH2Cl2. Fractions homogenous by TLC are combined, condensed and recrystallized from EtOAc/hexanes to yield 0.296 g of the desired product as a white solid.

Workup

  1. custompartitioned between EtOAc and H2O
  2. washThe aqueous layer is washed with EtOAc (3×)
  3. dry with materialThe combined organic layers are dried over Na2SO4 and condensed
  4. customto obtain a red-brown residue
  5. customchromatographed
  6. washeluting with 2% MeOH in CH2Cl2
  7. customcondensed
  8. customrecrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-feb59aa2d41e4f1998753e640136d72a
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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