Trifluoroacetic acid → 8-(4-Fluorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine

HRID 2179315Notes

Reaction equation

HRID 2179315 reaction equation
[F: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.FC(F)(F)C(O)=O>ClCCl>[F: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 6422Trifluoroacetic acidHCID 68108445HCID 68108445, compound

Product 1

HCID 681085938-(4-Fluorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridineYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the product obtained in step A (150 mg, 0.31 mmol) in dichloromethane (3 mL) was added trifluoroacetic acid (0.6 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, 90:10 dichloromethane/methanol) to give 8-(4-fluorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine (60 mg, 52%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.03 (d, J=1.8 Hz, 1H), 8.00-7.92 (m, 2H), 7.78 (dd, J=8.7, 2.1 Hz, 1H), 7.51 (d, J=9.0 Hz, 1H), 7.21-7.10 (m, 2H), 4.00 (t, J=2.1 Hz, 2H), 3.25 (t, J=5.7 Hz, 2H), 2.84-2.76 (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, 90:10 dichloromethane/methanol)

Sources & evidence

ORD record
ord-1286fbbaa6e145d5942b6a877c0ff405
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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