tert-Butylphosphine → HCID 57713362, compound

HRID 1983874Notes

Reaction equation

HRID 1983874 reaction equation
[S:1]1[C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[NH:5][C:4]=2[CH:3]=[CH:2]1.Br[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:16][CH:15]=1.C(O[Na])(C)(C)C.C(P)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C(C)=CC=CC=1>[CH2:21]([O:20][C:17]1[CH:16]=[CH:15][C:14]([N:5]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:12]3[S:1][CH:2]=[CH:3][C:4]2=3)=[CH:19][CH:18]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 123165tert-ButylphosphineHCID 145298p-Bromophenyl octyl etherHCID 12371552HCID 12371552, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 57713362HCID 57713362, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7237O-XyleneSolvent

Procedure

3.0 g (17.3 mmol) of 4H-thieno[3,2-b]indole (C′), 4.93 g (17.3 mmol) of 1-bromo-4-octyloxybenzene, and 0.0025 g (1.114×10−2 mmol) of tris(dibenzylideneacetone)dipalladium(0) were dissolved in 1.9 g (19.8 mmol) of t-BuONa, 0.003 g (1.5×102 mmol) of t-butylphosphine, and 50 ml of xylene and the solution was refluxed at 120° C. for 24 hours. Then, the solvent was removed and the resulting product was isolated and purified by column chromatography using toluene/hexane (⅓ by volume) as an eluent, thereby obtaining 5.35 g (yield: 82%) of 4-(4′-octyloxy-phenyl)-4H-thieno[3,2-b]indole (D′).

Workup

  1. customThen, the solvent was removed
  2. customthe resulting product was isolated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-a74520390fc44ce2a53dbbc09a335bd7
Source dataset
uspto-grants-2009_06
Patent number
US07541736B2

Reaction notes

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