HCID 21472367, compound → HCID 21472358, compound

HRID 2294895Notes

Reaction equation

HRID 2294895 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:15]=[C:14]([CH2:16][CH2:17][CH2:18][CH3:19])[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]4[N:37]([CH:38]([O:40][CH2:41][CH3:42])[CH3:39])[N:36]=[N:35][N:34]=4)=[CH:23][CH:22]=3)[C:5]2=[N:6][C:7]=1[CH:8]([O:11][CH3:12])[O:9][CH3:10]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:16]([C:14]1[N:13]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[N:37]([CH:38]([O:40][CH2:41][CH3:42])[CH3:39])[N:36]=[N:35][N:34]=3)=[CH:23][CH:22]=2)[C:5]2=[N:6][C:7]([CH:8]([O:11][CH3:12])[O:9][CH3:10])=[C:2]([C:5]3[CH:4]=[CH:3][CH:2]=[CH:7][N:6]=3)[CH:3]=[C:4]2[N:15]=1)[CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 1

HCID 21472367HCID 21472367, compound

Product 1

HCID 21472358HCID 21472358, compoundYield 111.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

0.7 g (1.1 mmole) of the compound obtained in step 9 was dissolved in 5 ml of toluene and to the resulting solution were added 486 mg (1.32 mmole) of 2-(tributyltin)-pyridine and 25 mg (0.022 mmole) of Pd(PPh3)4. The resultant was heated to reflux for 16 hours under argon gas, cooled and extracted with a mixture of ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified with column chromatography (ethyl acetate) to obtain 389 mg of the title compound (yield 56%).

Workup

  1. temperatureThe resultant was heated
  2. temperatureto reflux for 16 hours under argon gas
  3. temperaturecooled
  4. extractionextracted with a mixture of ethyl acetate and water
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b2e4d90581d94b0394478b76d9d6dfdb
Source dataset
uspto-grants-1997_11
Patent number
US05691348

Reaction notes

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