1,2-Dichloroethane → HCID 68183033, compound

HRID 1615518Notes

Reaction equation

HRID 1615518 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:17]3[CH:16]=[C:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[S:14][C:13]=3[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.ClCCCl.C([SiH](CC)CC)C.FC(F)(F)S(O)(=O)=O.C([O-])(O)=O.[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[CH:16]=[C:15]([C:18]4[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=4)[S:14][C:13]=3[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 681831404-(4-chlorophenyl)-2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-4-ol

Product 1

HCID 68183033HCID 68183033, compoundYield 95%

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(4-chlorophenyl)-2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-4-ol (745.8 mg, 2.10 mmol) in 1,2-dichloroethane (11.0 mL, 140 mmol) were added triethylsilane (3.35 mL, 20.9 mmol) and trifluoromethanesulfonic acid (0.927 mL, 10.5 mmol) and the resulting reddish solution was heated at 100° C. for 16 hr. The reaction mixture was allowed to cool to rt then was neutralized to pH 7 by the addition of a saturated NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×10 mL). The organic layers were combined, washed with brine, dried over MgSO4, filtered, concentrated and the obtained residue was purified by column chromatography (SiO2, elution with 0-100% EA/DCM) to give the title compound as a white foam (587.4 mg, 95% yield). LCMS: (FA) ES+ , 354. 1H NMR (400 MHz, DMSO-d6) δ: 8.45-8.49 (dd, J=1.5 Hz, J=4.7 Hz, 2H), 7.36-7.44 (m, 4H), 7.16-7.20 (dd, J=8.2 Hz, 2H), 7.10-7.12 (br s, 1H), 4.28-4.33 (m, 1H), 2.75-3.0 (m, 2H), 2.10-2.20 (m, 1H), 1.88-1.95 (m, 1H), 1.60-1.80 (m, 4H).

Workup

  1. temperatureto cool to rt
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe obtained residue was purified by column chromatography (SiO2, elution with 0-100% EA/DCM)

Sources & evidence

ORD record
ord-b26d94ebc9ec4a70b32522ade4c189c1
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

Loading…