Tributylphosphine → 5-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-1H-indole

HRID 1163308Notes

Reaction equation

HRID 1163308 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][OH:16])[CH:10]=1.O[C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[CH:21]2.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.C(OCC)C>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[NH:23][CH:22]=[CH:21]3)[CH:10]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 160545-HydroxyindoleHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 230827203-(2,6-Dimethylphenyl)benzyl alcohol

Product 1

HCID 231117535-[(2',6'-dimethylbiphenyl-3-yl)methoxy]-1H-indoleYield 62%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2′,6′-dimethylbiphenyl-3-yl)methanol (1.0 g, 4.71 mmol), 5-hydroxyindole (0.63 g, 4.73 mmol) and tributylphosphine (1.5 mL, 6.02 mmol) in tetrahydrofuran (30 mL) was stirred, and 1,1′-(azodicarbonyl)dipiperidine (1.6 g, 6.34 mmol) was added by portions, and the mixture was stirred at room temperature for 18 hr. Diethyl ether (30 mL) was added to the reaction mixture, and the precipitated insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10-1:5) to give the title compound (0.95 g, yield 62%) as a pale-brown oil.

Workup

  1. filtrationthe precipitated insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10-1:5)

Sources & evidence

ORD record
ord-f556ca16b72f4c40b0c4a516abb71e51
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

Loading…