Indole → HCID 10512013, compound

HRID 1173526Notes

Reaction equation

HRID 1173526 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.CC(C)([O-])C.[Na+].[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16]1.C1C=CC(P(C2C(OC3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=3)=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.[C].[Pd]>[N:6]1[CH:7]=[CH:8][C:3]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 798IndoleHCID 818524-Chloropyridine hydrochlorideHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 23676156Sodium t-butoxide

Product 1

HCID 10512013HCID 10512013, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 1140TolueneSolvent

Procedure

In 600 mL of toluene were dissolved 30.0 g (0.20 mol) of 4-chloropyridine hydrochloride, 53.8 g (0.56 mol) of sodium t-butoxide, 19.6 g (0.01 mol) of 10 w/w % palladium-carbon (Pd—C) (containing 54 w/w % water), 23.4 g (0.20 mol) of indole, and 5.39 g (0.01 mol) of DPEphos. The resultant mixture was stirred for 10 hours with refluxing. After completion of the reaction, the reaction mixture was cooled to room temperature and the palladium-carbon was filtered off. This liquid reaction mixture was concentrated. 300 mL of ethyl acetate and 300 mL of 1-M hydrochloric acid were added to the residue to extract the target compound with the aqueous layer. Subsequently, 300 mL of ethyl acetate and 200 mL of 2-M aqueous sodium hydroxide solution were added to the aqueous layer to extract the target compound with the organic layer this time. This organic layer was washed with 200 mL of water and then dried with magnesium sulfate. The organic layer was filtered and concentrated to obtain 33.3 g (yield, 86%) of the target compound as an oily substance. The purity thereof was 99.8%.

Workup

  1. temperaturewith refluxing
  2. customAfter completion of the reaction
  3. filtrationthe palladium-carbon was filtered off
  4. customThis liquid reaction mixture
  5. concentrationwas concentrated
  6. addition300 mL of ethyl acetate and 300 mL of 1-M hydrochloric acid were added to the residue
  7. extractionto extract the target compound with the aqueous layer
  8. additionSubsequently, 300 mL of ethyl acetate and 200 mL of 2-M aqueous sodium hydroxide solution were added to the aqueous layer
  9. extractionto extract the target compound with the organic layer this time
  10. washThis organic layer was washed with 200 mL of water
  11. dry with materialdried with magnesium sulfate
  12. filtrationThe organic layer was filtered
  13. concentrationconcentrated
  14. customto obtain
  15. custom33.3 g (yield, 86%) of the target compound as an oily substance

Sources & evidence

ORD record
ord-ec2be5a5526d4bf6a55efb0b85492b5f
Source dataset
uspto-grants-2010_11
Patent number
US07834183B2

Reaction notes

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