Ethyl Acetate → HCID 58885235, compound

HRID 1766279Notes

Reaction equation

HRID 1766279 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11]1[CH:16]=[CH:15][N:14]([CH3:17])[CH2:13][CH:12]=1.[CH:28]([Sn](CCCC)(CCCC)CCCC)=[CH2:29].C(OCC)(=O)C>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:28]([C:2]1[CH:3]=[C:4]([O:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH:11]1[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]1)=[CH2:29]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 81998TributylvinyltinHCID 86592478HCID 86592478, compound

Product 1

HCID 58885235HCID 58885235, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of benzenesulfonic acid 7-bromo-3-(1-methylpyridin-4-yl)-1H-indol-5-yl ester and Pd (PPh3)4 (0.2 eq.) in dry toluene was degassed and then treated with vinyl tributyltin (1.1 eq.). Heat the reaction mixture to reflux. After 5 hours, cool to room temperature, pour into ethyl acetate, wash with brine, dry the organic layer over Na2SO4, and concentrate. Purify to give the title compound.

Workup

  1. customwas degassed
  2. temperatureHeat the reaction mixture
  3. temperatureto reflux
  4. washwash with brine
  5. dry with materialdry the organic layer over Na2SO4
  6. concentrationconcentrate
  7. customPurify

Sources & evidence

ORD record
ord-270fc990a2274d6dadf16267e560637e
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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