Tri-tert-butylphosphine tetrafluoroborate → HCID 68954792, compound

HRID 750998Notes

Reaction equation

HRID 750998 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][NH:9][C:10]2[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=2)[C:13](OCCCC)=[O:14])[CH:2]=1.[CH:23]1([O:28][C:29]2[CH:30]=[C:31](I)[CH:32]=[CH:33][C:34]=2[O:35][CH3:36])[CH2:27][CH2:26][CH2:25][CH2:24]1.[CH3:38][C:39]([CH3:42])([O-:41])[CH3:40].[Na+].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1>[CH:23]1([O:28][C:29]2[CH:30]=[C:31]([N:9]([CH2:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[C:10]3[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=3)[C:13]([O:41][C:39]([CH3:42])([CH3:40])[CH3:38])=[O:14])[CH:32]=[CH:33][C:34]=2[O:35][CH3:36])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 111979243-cyclopentyloxy-4-methoxyiodobenzeneHCID 23676156Sodium t-butoxideHCID 69205850HCID 69205850, compound

Product 1

HCID 68954792HCID 68954792, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 103 mg of 1-butyl N-(2-(3-pyridyl)ethyl)-3-aminobenzoate (0.35 mmol) and 200 mg of 3-cyclopentyloxy-4-methoxyiodobenzene (0.63 mmol) in 5 mL of toluene was added 100 mg of sodium t-butoxide (1.0 mmol), 15 mg of tri-t-butylphosphonium tetrafluoroborate (0.05 mmol) and 25 mg of tris(dibenzylidineacetone)dipalladium(0) (0.028 mmol). The mixture was stirred for 16 h and filtered through celite. The celite was washed with 3×5 mL of toluene and the filtrate was concentrated in vacuo. The residue was purified by column chromatography using 30%-40% EtOAc in hexanes as eluant to give 48 mg of t-butyl N-(3-cyclopentyloxy-4-methoxyphenyl)-N-(2-(3-pyridyl)ethyl)-3-aminobenzoate.

Workup

  1. filtrationfiltered through celite
  2. washThe celite was washed with 3×5 mL of toluene
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a5233a5c3c9c48b4b75be798b40777f9
Source dataset
uspto-grants-2008_07
Patent number
US07405230B2

Reaction notes

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