Potassium Phosphate, Tribasic → Methyl(4-cyclopropyl-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate

HRID 591506Notes

Reaction equation

HRID 591506 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH2:4][C:5]1[C:9]2[C:10](OS(C(F)(F)F)(=O)=O)=[CH:11][C:12]([O:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:13][C:8]=2[S:7][CH:6]=1.[CH:34]1(B(O)O)[CH2:36][CH2:35]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2].O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:33])[CH2:4][C:5]1[C:9]2[C:10]([CH:34]3[CH2:36][CH2:35]3)=[CH:11][C:12]([O:14][Si:15]([CH:22]([CH3:23])[CH3:24])([CH:19]([CH3:20])[CH3:21])[CH:16]([CH3:18])[CH3:17])=[CH:13][C:8]=2[S:7][CH:6]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 131734520Methyl(4-(((trifluoromethyl)sulfonyl)oxy)-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 131734522Methyl(4-cyclopropyl-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetateYield 91.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl(4-(((trifluoromethyl)sulfonyl)oxy)-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate (512 mg) and DMF (10 mL) were added cyclopropylboronic acid (167 mg), potassium phosphate (1238 mg), Pd(OAc)2 (21.83 mg) and tricyclohexylphosphine (82 mg) at room temperature, and the mixture was refluxed for 16 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (372 mg).

Workup

  1. temperaturethe mixture was refluxed for 16 h
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed successively with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-7dff6fd2eecb4fe98a755433b3f20f07
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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