HCID 68109542, compound → HCID 68109120, compound

HRID 2179419Notes

Reaction equation

HRID 2179419 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][N:12](CC4C=CC(OC)=CC=4)[CH:11]([CH2:24][F:25])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH:3]=1>O.CC(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][NH:12][CH:11]([CH2:24][F:25])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:27])=[O:28])[CH:3]=1

Participants

5

Reactant 1

HCID 68109542HCID 68109542, compound

Product 1

HCID 68109120HCID 68109120, compoundYield 12%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ceric ammonium nitrate (800 mg, 1.46 mmol) in water (1 mL) was added to a solution of the product obtained in step C (90 mg, 0.18 mmol) in acetone (10 mL). The resulting red solution was stirred at ambient temperature for 1.5 h, diluted with ethyl acetate, washed sequentially with saturated aqueous NaHCO3 and brine then dried over anhydrous MgSO4. The solution was filtered and the filtrate concentrated in vacuo to give the crude product which was purified by flash column chromatography (SiO2, 9:1 to 1:1 hexanes/ethyl acetate) providing 6-chloro-1-(fluoromethyl)-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine (8 mg, 12%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 8.14 (d, J=1.5 Hz, 1H), 7.98-7.95 (m, 2H), 7.85 (d, J=1.8 Hz, 1H), 7.57-7.48 (m, 3H), 5.72-5.54 (m, 1H), 3.68-3.58 (m, 1H), 3.42-3.28 (m, 2H), 3.26-3.18 (m, 1H), 3.13-3.00 (m, 2H).

Workup

  1. washwashed sequentially with saturated aqueous NaHCO3 and brine
  2. dry with materialthen dried over anhydrous MgSO4
  3. filtrationThe solution was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customto give the crude product which
  6. customwas purified by flash column chromatography (SiO2, 9:1 to 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-ff5308e626bd46ee91ff7a13f13759c9
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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