Trifluoroacetic acid → HCID 68109725, compound

HRID 2179439Notes

Reaction equation

HRID 2179439 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][C:10]=3[C:6]=2[CH:5]=[C:4]([C:22](O)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH3:23])[CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[C:6]=2[CH:5]=[C:4]([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH2:23])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68109018HCID 68109018, compound

Product 1

HCID 68109725HCID 68109725, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of step A (60.0 mg, 0.14 mmol) in dichloromethane (6 mL) was added trifluoroacetic acid (0.5 mL). After stirring for 2 h at ambient temperature the reaction mixture was quenched with 10% sodium bicarbonate solution (15 mL) and extracted with dichloromethane. The organic extract was dried over sodium sulphate and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 9:1 dichloromethane/methanol) affording 6-chloro-8-(1-phenylvinyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine (40 mg, 74%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 7.36-7.31 (m, 5H), 7.24-7.20 (m, 2H), 5.47 (d, J=11.4 Hz, 2H), 3.92 (t, J=1.8 Hz, 2H), 3.24 (t, J=5.7 Hz, 2H), 2.84 (t, J=5.7 Hz, 2H)

Workup

  1. customwas quenched with 10% sodium bicarbonate solution (15 mL)
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. dry with materialwas dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, 9:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-05f4f581f0a84368b27b81f7c94809a8
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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