Triethylamine → HCID 59010042, compound

HRID 2118104Notes

Reaction equation

HRID 2118104 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C:11]2=[O:14])=[CH:7][CH:6]=1.C(N(CC)CC)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O>C1(C)C=CC=CC=1.C(OCC)C.C(=O)(O)[O-].[Na+].C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:18]=[C:17]([C:19]([F:20])([F:22])[F:21])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][C:11]2=[O:14])=[CH:7][CH:6]=1

Participants

9

Reactant 3

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 59010060HCID 59010060, compound

Product 1

HCID 59010042HCID 59010042, compound

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 6-[2-chloro-4-(trifluoromethyl)phenoxy]indan-1-one (200 mg, 0.612 mmol) in toluene (5.0 mL) at 0° C. under nitrogen was added triethylamine (0.104 mL, 0.734 mmol) followed by trimethylsilyl trifluoromethanesulfonate (0.140 g, 0.612 mmol). The reaction warmed to room temperature and stirred for 10 min, then was diluted with diethyl ether and saturated sodium bicarbonate. The aqueous layer was extracted with diethyl ether and the combined organic layers were washed with brine, dried with magnesium sulfate, filtered and concentrated. The resulting residue was dissolved in dichloromethane (1.0 mL) and added via canula at room temperature in the dark to a suspension of Pd(OAc)2 (134 mg, 0.60 mmol) in acetonitrile (4.0 mL). The resulting reaction mixture stirred 1.25 h, then was diluted with diethyl ether, filtered through celite and concentrated to provide the final product as yellow oil which was carried forward without further purification.

Workup

  1. extractionThe aqueous layer was extracted with diethyl ether
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe resulting residue was dissolved in dichloromethane (1.0 mL)
  7. customThe resulting reaction mixture
  8. stirringstirred 1.25 h
  9. filtrationfiltered through celite and
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-a8ec32f3291d4948b644d76ce26c92fe
Source dataset
uspto-grants-2008_10
Patent number
US07442808B2

Reaction notes

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