Dichloromethane → HCID 68183081, compound

HRID 1615519Notes

Reaction equation

HRID 1615519 reaction equation
[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:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[S:14][C:13]=3[CH:12]([OH:24])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(Cl)Cl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=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[C:12](=[O:24])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 68183118HCID 68183118, compound

Product 1

HCID 68183081HCID 68183081, compoundYield 50%

Procedure

The reaction mixture was quenched with saturated sodium bisulfite then was cooled to rt and insoluble materials were removed by filtration. The pH of the filtrate was adjusted to 9 by the addition of a saturated NaHCO3 solution and the organic layer was separated. To the aqueous layer was added saturated NH4Cl solution (5 mL) and it was then extracted with DCM (3×20 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated. The obtained residue, 4-(4-chlorophenyl)-2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-8-ol (3.17 g, 8.30 mmol), was dissolved in methylene chloride (1217 mL, 580 mmol) and Dess-Martin periodinane (3.9 g, 9.20 mmol) was added. The reaction mixture was stirred for 16 h at rt. The reaction mixture was neutralized to pH ˜7 by the addition of NaHCO3, the organic layer was separated, and the aqueous layer was extracted with DCM (3×20 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated. The obtained residue was purified by column chromatography (SiO2, elution with 0-100% EA/hexane) to give the title compound as a white solid (1.34 g, 50% yield). LCMS: (AA) ES+ , 354. 1H NMR (400 MHz, DMSO-d6) δ: 8.51-8.54 (dd, J=1.5 Hz, J=4.5 Hz, 2H), 8.12-8.18 (m, 1H), 7.51-7.54 (dd, J=1.5 Hz, J=4.5 Hz, 2H), 7.34-7.38 (m, 2H), 7.15-7.17 (br s, 2H), 7.13-7.14 (br s, 1H), 4.26-4.31 (m, 1H), 3.10-3.28 (m, 1H), 2.05-2.15 (m, 1H), 1.80-1.90 (m, 2H), 1.50-1.72 (m, 2H).

Workup

  1. customThe reaction mixture was quenched with saturated sodium bisulfite
  2. custominsoluble materials were removed by filtration
  3. additionThe pH of the filtrate was adjusted to 9 by the addition of a saturated NaHCO3 solution
  4. customthe organic layer was separated
  5. additionTo the aqueous layer was added saturated NH4Cl solution (5 mL) and it
  6. extractionwas then extracted with DCM (3×20 mL)
  7. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe organic layer was separated
  11. extractionthe aqueous layer was extracted with DCM (3×20 mL)
  12. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe obtained residue was purified by column chromatography (SiO2, elution with 0-100% EA/hexane)

Sources & evidence

ORD record
ord-03adc7e6b83d4c9f842ae33ddb550f0b
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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