Hydrochloric Acid → 8-(4-Chlorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride

HRID 2179318Notes

Reaction equation

HRID 2179318 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:23][C:22]4[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][C:17]=4[C:15]=3[CH:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:23][C:22]4[CH2:21][CH2:20][NH:19][CH2:18][C:17]=4[C:15]=3[CH:16]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68109196HCID 68109196, compound

Product 1

HCID 681090598-(4-Chlorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochlorideYield 160.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The product of step A (118 mg, 0.26 mmol) was Boc-deprotected by treating with 4N HCl in dioxane (2 mL). After stirring for 2 h at ambient temperature the reaction mixture was quenched with 10% sodium bicarbonate solution (20 mL) and extracted with dichloromethane. The organic extract was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 95:5 chloroform/methanol) to give 8-(4-chlorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (80 mg, 87%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.02 (d, J=1.8 Hz, 1H), 7.91-7.84 (m, 2H), 7.78 (dd, J=8.7, 2.1 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 7.48-7.41 (m, 2H), 3.99 (t, J=2.1 Hz, 2H), 3.24 (t, J=5.7 Hz, 2H), 2.85-2.76 (m, 2H).

Workup

  1. customwas quenched with 10% sodium bicarbonate solution (20 mL)
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, 95:5 chloroform/methanol)

Sources & evidence

ORD record
ord-a2758053613a4e45891d4f7abd565736
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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