HCID 19776904, compound → HCID 19776910, compound

HRID 1612871Notes

Reaction equation

HRID 1612871 reaction equation
Br[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([O:12][CH3:13])[C:5]([CH:14]=[O:15])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[O:21][CH2:22][C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([O:30][CH3:31])[C:24]=1[S:32][Sn](CCCC)(CCCC)CCCC)CCC>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>[CH:14]([C:5]1[CH:4]=[CH:3][C:2]([S:32][C:24]2[C:25]([O:30][CH3:31])=[CH:26][C:27]([CH3:29])=[CH:28][C:23]=2[CH2:22][OH:21])=[C:7]([C:6]=1[O:12][CH3:13])[C:8]([O:10][CH3:11])=[O:9])=[O:15]

Participants

5

Reactant 2

HCID 19776904HCID 19776904, compoundHCID 67854024HCID 67854024, compound

Product 1

HCID 19776910HCID 19776910, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

1.08 g (3.94 mmol) of the compound from Example 5 and 2 g (2.6 mmol) of the compound from Example 16 and 30 mg of tetrakis(triphenylphosphine)palladium are heated under reflux in 40 ml of toluene under a nitrogen atmosphere for 50 h. After concentrating in vacuo, the residue is taken up in acetonitrile and washed five times with pentane. The acetonitrile phase is concentrated in vacuo and the remaining oil (1.33 g) is chromatographed on a silica gel column using ethyl acetate/petroleum ether 1:5.

Workup

  1. concentrationAfter concentrating in vacuo
  2. washwashed five times with pentane
  3. concentrationThe acetonitrile phase is concentrated in vacuo
  4. customthe remaining oil (1.33 g) is chromatographed on a silica gel column

Sources & evidence

ORD record
ord-6f1c855d52474908b1a9f7c94d617ee0
Source dataset
uspto-grants-1993_03
Patent number
US05190971

Reaction notes

Loading…