Triethylamine → HCID 86760309, compound

HRID 857313Notes

Reaction equation

HRID 857313 reaction equation
Br[C:2]1[N:3]([CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]/[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.CCN(CC)CC>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-]>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]3[CH2:19][CH2:20][CH2:21]/[C:22](=[CH:23]/[C:24]([O:26][CH2:27][CH3:28])=[O:25])/[C:2]=23)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86760308HCID 86760308, compound

Product 1

HCID 86760309HCID 86760309, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a vigorously stirred solution of 0.13 g of the product from Step 5 in 4 mL of DMF under N2 atmosphere was added sequentially 0.75 g of n-Bu4NCl, 0.1 mL of Et3N and 0.022 g of Pd(AcO)2. The mixture was stirred for 1 hour at 75° C. and then concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluted with 6:1 hexane/EtOAc to give 0.07 g of the more mobile isomer followed by 0.06 g of the less mobile isomer.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel flash chromatography
  3. washeluted with 6:1 hexane/EtOAc
  4. customto give 0.07 g of the more mobile isomer

Sources & evidence

ORD record
ord-a65130786a574c39988f150716a79d02
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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